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{{use dmy dates|date=November 2022}} |
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{{chembox |
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{{chembox |
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| Verifiedfields = changed |
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| verifiedrevid = 408988451 |
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| Watchedfields = changed |
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| Name = Resorcinol |
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| verifiedrevid = 415763656 |
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| ImageFileL1 = Resorcinol.svg |
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| Name = Resorcinol |
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| ImageSizeL1 = 120px |
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| ImageFileL1 = Resorcinol.svg |
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| ImageNameL1 = Skeletal formula |
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| ImageSizeL1 = 150px |
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| ImageFileR1 = Resorcinol-3D-balls.png |
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| ImageNameL1 = Skeletal formula |
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| ImageSizeR1 = 120px |
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| ImageFileR1 = Resorcinol-3D-balls.png |
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| ImageNameR1 = Ball-and-stick model |
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| ImageNameR1 = Ball-and-stick model |
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| IUPACName = Benzene-1,3-diol |
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| ImageSizeR1 = 100px |
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| OtherNames = Resorcin<br />m-dihydroxybenzene; 1,3-benzenediol; 1,3-Dihydroxybenzene; 3-Hydroxyphenol; m-hydroquinone; m-benzenediol; 3-hydroxycyclohexadien-1-one |
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| PIN = Benzene-1,3-diol<ref name=iupac2013>{{cite book | title = Nomenclature of Organic Chemistry: IUPAC Recommendations and Preferred Names 2013 (Blue Book) | publisher = ] | date = 2014 | location = Cambridge | page = 691 | doi = 10.1039/9781849733069-FP001 | isbn = 978-0-85404-182-4| chapter = Front Matter }}</ref> |
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| Section1 = {{Chembox Identifiers |
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| OtherNames = Resorcinol<ref name=iupac2013 /><br />Resorcin<br />''m''-Dihydroxybenzene<br />1,3-Benzenediol<br /> 1,3-Dihydroxybenzene<br />3-Hydroxyphenol<br />''m''-Benzenediol |
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| SMILES = c1cc(cc(c1)O)O |
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|Section1={{Chembox Identifiers |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChEBI_Ref = {{ebicite|changed|EBI}} |
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| ChEBI = 27810 |
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| SMILES = c1cc(cc(c1)O)O |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID = 4878 |
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| ChemSpiderID = 4878 |
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| PubChem = 5054 |
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| PubChem = 5054 |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| CASNo = 108-46-3 |
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| CASNo = 108-46-3 |
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| UNNumber = 2876 |
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| UNNumber = 2876 |
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}} |
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}} |
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| Section2 = {{Chembox Properties |
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|Section2={{Chembox Properties |
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| Formula = C<sub>6</sub>H<sub>6</sub>O<sub>2</sub> |
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| Formula = C<sub>6</sub>H<sub>6</sub>O<sub>2</sub> |
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| MolarMass = 110.1 g/mol |
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| MolarMass = 110.111 g/mol |
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| Appearance = White solid |
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| Appearance = White solid<ref name=PGCH/> |
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| Odor = Faint<ref name=PGCH/> |
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| Density = 1.28 g/cm<sup>3</sup>, solid |
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| Density = 1.28 g/cm<sup>3</sup>, solid |
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| Solubility = 110 g/100 mL at 20 °C |
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| Solubility = 110 g/100 mL at 20 °C |
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| MeltingPtC = 110 |
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| BoilingPtC = 277 |
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| MeltingPtC = 110 |
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| BoilingPtC = 277 |
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| pKa = 9.15<ref>Gawron, O., Duggan, M., Grelechi, C., ''J. Anal. Chem.'', '''1952''', ''24'', 969.</ref> |
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| pKa = 9.15<ref>{{cite journal | last1 = Gawron | first1 = O. | last2 = Duggan | first2 = M. | last3 = Grelechi | first3 = C. | year = 1952 | title = Manometric Determination of Dissociation Constants of Phenols| doi = 10.1021/ac60066a013 | journal = Analytical Chemistry| volume = 24 | issue = 6| pages = 969–970 }}</ref> |
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| VaporPressure = 0.0002 mmHg (25 °C)<ref name=PGCH/> |
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| Dipole = {{val|2.07|0.02|u=]}}<ref>{{cite journal|doi=10.1021/ja01218a051|title=The Dipole Moments of Catechol, Resorcinol and Hydroquinone|year=1945|last1=Lander|first1=John J.|last2=Svirbely|first2=John J. Lander, W. J.|journal=Journal of the American Chemical Society|volume=67|issue=2|pages=322–324|bibcode=1945JAChS..67..322L }}</ref> |
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| MagSus = {{val|-67.26e-6|u=cm<sup>3</sup>/mol}} |
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| RefractIndex = 1.578<ref name="CRC97">{{Cite book |title=CRC handbook of chemistry and physics: a ready-reference book of chemical and physical data. |date=2016 |others=William M. Haynes, David R. Lide, Thomas J. Bruno |isbn=978-1-4987-5428-6 |edition=2016-2017, 97th |location=Boca Raton, Florida |oclc=930681942}}</ref> |
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}} |
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| Section3 = {{Chembox Structure |
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| Section4 = {{Chembox Thermochemistry |
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| DeltaHform = -368.0 kJ·mol<sup>−1</sup><ref name="CRC97"/> |
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| Dipole = |
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| DeltaHfus = 20.4 kJ·mol<sup>−1</sup><ref name="CRC97"/> |
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}} |
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}} |
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| Section7 = {{Chembox Hazards |
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|Section6={{Chembox Pharmacology |
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| ExternalMSDS = |
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| ATCCode_prefix = D10 |
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| EUClass = Harmful ('''Xn''')<br />Dangerous for<br />the environment ('''N''') |
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| ATCCode_suffix = AX02 |
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| ATC_Supplemental = {{ATC|S01|AX06}} |
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}} |
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|Section7={{Chembox Hazards |
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| GHSPictograms = {{GHS05}}{{GHS07}}{{GHS09}} |
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| HPhrases = {{H-phrases|302|313|315|318|400}} |
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| PPhrases = {{P-phrases|273|280|305+351+338}} |
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| ExternalSDS = |
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| FlashPtF = 261 |
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| FlashPt_ref =<ref name=PGCH/> |
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| AutoignitionPtC = 608 |
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| AutoignitionPt_ref =<ref name="CRC97"/> |
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| PEL = none<ref name=PGCH>{{PGCH|0543}}</ref> |
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| ExploLimits = 1.4%-?<ref name=PGCH/> |
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| IDLH = N.D.<ref name=PGCH/> |
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| REL = TWA 10 ppm (45 mg/m<sup>3</sup>) ST 20 ppm (90 mg/m<sup>3</sup>)<ref name=PGCH/> |
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}} |
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'''Resorcinol''' (or '''resorcin''') is a phenolic compound. It is an ] with the formula C<sub>6</sub>H<sub>4</sub>(OH)<sub>2</sub>. It is one of three ]ic ]s, the 1,3-isomer (or '']''-isomer). Resorcinol crystallizes from ] as colorless needles that are readily soluble in water, alcohol, and ether, but insoluble in ] and ].<ref name="Ullmann">{{Ullmanns|title=Resorcinol|author=K. W. Schmiedel |author2=D. Decker |doi=10.1002/14356007.a23_111.pub2|year=2012}}</ref> |
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'''Resorcinol''' (or '''resorcin''') is a dihydroxy ]. It is the 1,3-] of ] with the ] C<sub>6</sub>H<sub>4</sub>(OH)<sub>2</sub>. |
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==Nomenclature== |
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Benzene-1,3-diol is the name recommended by the ] (IUPAC) in its ''1993 Recommendations for the Nomenclature of Organic Chemistry''.<ref>{{cite book | author=Panico, R.; & Powell, W. H. (Eds.) | title=A Guide to IUPAC Nomenclature of Organic Compounds 1993 | location=Oxford | publisher=Blackwell Science | year=1994 | isbn=0-632-03488-2}}</ref> |
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==Production== |
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==Production== |
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Resorcinol is produced in several steps from benzene, starting with dialkylation with ] to give ]. Oxidation and ] of this disubstituted arene gives acetone and resorcinol.<ref name="Ullmann" /> |
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It is produced when any of a large number of ]s (e.g. ], ], etc.) are melted with ], or by the ] of ] extract. It may be prepared ] by melting ], ] or ] with ]; by the action of ] on ]; or by the action of 10% ] on ]<ref>{{cite journal|journal = Ber | first = J |last = Meyer | year = 1897 |pages = 2569 |volume = 30}}</ref>. Many ''ortho''- and ''para''-compounds of the ] series (for example, the bromophenols, benzene-''para''-disulfonic acid) also yield resorcinol on fusion with potassium hydroxide. |
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] |
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Resorcinol is an expensive chemical, produced in only a very few locations around the world (as of 2010 only four commercial plants were known to be operative: in the United States, Germany, China, and Japan), and as such it is the determining factor in the cost of ] adhesives.<ref>Wood adhesives, </ref> Production in the United States ended in 2017 with the closure of Indspec Chemical's plant in Petrolia, Pennsylvania.<ref>{{cite web |last1=McCoy |first1=Michael |title=Resorcinol plant to close |url=https://cen.acs.org/articles/95/i14/Resorcinol-plant-close.html |website=Chemical & Engineering News |publisher=American Chemical Society |access-date=6 December 2023}}</ref> |
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Many additional routes exist for resorcinol. It was formerly produced by disulfonation of benzene followed by hydrolysis of the 1,3-disulfonate. This method has been discarded because it cogenerates so much sulfur-containing waste. Resorcinol can also be produced when any of a large number of ]s (such as ] and ]) are melted with ], or by the ] of ] extract. It may be ] by melting ], phenol-3-sulfonic acid with ]. Diazotization of ] or on ] followed by hydrolysis provides yet another route.<ref>{{cite journal|journal = Berichte der Deutschen Chemischen Gesellschaft| first = J |last = Meyer | year = 1897 |pages = 2568–2569 |volume = 30| issue = 3 |doi =10.1002/cber.18970300334 | title =Notiz über die Umwandlung von Aminen in Phenole| url = https://zenodo.org/record/1425892 }}</ref> Many '']''- and '']''-compounds of the ] series (for example, the ], benzene-''para''-disulfonic acid) also yield resorcinol on fusion with potassium hydroxide. |
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==Properties== |
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==Reactions== |
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Resorcinol crystallizes from ] as colorless needles which are readily soluble in water, alcohol and ether, but insoluble in ] and ]. It reduces ], and ]. It does not form a precipitate with ] solution, as the isomeric ] does. ] colors its aqueous solution a dark violet, and ] water precipitates tribromoresorcin. These properties are what give it its use as a colouring agent for certain ] experiments. ] reduces it to dihydroresorcin, which when heated to 150 to 160 °C with concentrated ] solution gives γ-acetylbutyric acid (D. Vorlgnder); when fused with potassium hydroxide, resorcinol yields ], pyrocatechol and ]. It ] with ]s or ]s, in the presence of dehydrating agents, to oxyketones, e.g. |
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Partial ] of resorcinol gives ], also known as 1,3-cyclohexanedione.<ref name=OS>{{cite journal|title=Dihydroresorcinol|first1=R. B. |last1=Thompson|journal=Org. Synth.|year=1947|volume=27|page=21|doi=10.15227/orgsyn.027.0021}}</ref><ref>{{cite journal|title=Methyl-1,3-Cyclohexanedione|first1=A. B. |last1=Mekler|first2=S.|last2=Ramachandran|first3=S.|last3=Swaminathan|first4=Melvin S.|last4=Newman|journal=Org. Synth.|year=1961|volume=41|page=56|doi=10.15227/orgsyn.041.0056}}</ref> |
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with ] and glacial ] at 145 °C it yields resacetophenone (HO)<sub>2</sub>C<sub>6</sub>H<sub>3</sub>~CO.CH<sub>3</sub>(M. Nencki and N. Sieber, Jour. prak. Chem., 1881, 23, p. 147). With the ]s of dibasic acids it yields ]s. When heated with ]—] to 200 °C it yields meta-dioxydiphenylamine (A. Seyewitz, Bull. Soc. Chins., 1890, 3, p. 811). With ] it forms a water-soluble blue dye, which is turned red by acids, and is used as an ], under the name of lacmoid (M. C. Traub and C. Hock, Ber., 1884, 17, p. 2615). It condenses readily with ]s, yielding with ], on the addition of catalytic ], methylene diresorcin <sub>2</sub>•CH<sub>2</sub>, whilst with ], in the presence of ], it yields the ] of tetra-oxydiphenyl methane |
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carboxylic acid (J. T. Hewitt and F. G. Pope, Jour. C/tern. Soc., 1897, 75, p. 1084). In alcoholic solution it condenses with ] to form 4-methylumbelliferone (A. Michael, Jour. prak. Chem., 1888, 37, 470). |
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It reduces ] and ]. It does not form a precipitate with ] solution, as does the isomeric ]. ] colors its aqueous solution a dark-violet, and ] water precipitates tribromoresorcinol. These properties are what give it its use as a colouring agent for certain ] experiments. |
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In addition to electrophilic aromatic addition, resorcinol (and other poly-ols)undergo nucleophilic substitution via the enone form. |
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] reduces it to dihydroresorcin, which when heated to 150 to 160 °C with concentrated ] solution gives γ-acetylbutyric acid.{{Citation needed|date=February 2022}} |
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With concentrated ], in the presence of cold concentrated ], it yields trinitro-resorcin (]), which forms yellow crystals, exploding violently on rapid heating. |
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When fused with potassium hydroxide, resorcinol yields ], ], and ]. It ] with ]s or ]s, in the presence of dehydrating agents, to oxyketones, for example, with ] and glacial ] at 145 °C it yields resacetophenone (HO)<sub>2</sub>C<sub>6</sub>H<sub>3</sub>COCH<sub>3</sub>.<ref>{{cite journal| journal = Journal für Praktische Chemie | title =Über die Verbindungen der ein- und zweibasischen Fettsäuren mit Phenolen | pages=147–156| first1=M. | last1= Nencki | first2= N. | last2= Sieber | doi= 10.1002/prac.18810230111| year = 1881 | volume = 23| issue =1 | url =https://zenodo.org/record/1427886 }}</ref> With the ]s of dibasic acids, it yields ]s. When heated with ]—] to 200 °C it yields ''meta''-dioxydiphenylamine.<ref>A. Seyewitz, Bull. Soc. Chins., 1890, 3, p. 811</ref> |
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==Occurrence== |
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Parts of a molecule of ], another natural compound which is present in ], has the resorcinol skeleton structure in it. |
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With ] it forms a water-soluble blue dye, which is turned red by acids, and is used as a ] under the name of ].<ref>{{cite journal | title = Ueber ein Lakmoid | doi = 10.1002/cber.188401702192 | first1 = M. C. | last1= Traub | first2= C. | last2 = Hock | journal = Berichte der Deutschen Chemischen Gesellschaft| year = 1884 | volume = 17 | issue = 2 | pages= 2615–2617| url = https://zenodo.org/record/1425349 }}</ref> It condenses readily with ]s, yielding with ], on the addition of catalytic ], methylene diresorcin <sub>2</sub>CH<sub>2</sub>. Reaction with ] in the presence of ] yields the ] of tetra-oxydiphenyl methane carboxylic acid.<ref>J. T. Hewitt and F. G. Pope, Jour. C/tern. Soc., 1897, 75, p. 1084</ref> In alcoholic solution it condenses with ] to form ].<ref>{{cite journal | journal = Journal für Praktische Chemie |year =1888| volume = 37 |issue =1| title =Ueber das Verhalten von Natriummalonäther gegen Resorcinol| pages =469–471 | first1=Arthur | last1=Michael| doi= 10.1002/prac.18880370144|url =https://zenodo.org/record/1427932}}</ref> |
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==Applications== |
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===Medical=== |
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Used externally it is an ] and ], and is used 5 to 10% in ointments in the treatment of chronic skin diseases such as ], ] and ] of a sub-acute character.{{Citation needed|date=October 2007}} It is present in over-the-counter topical ] treatments at 2% or less concentration, and in prescription treatments at higher concentrations.{{Citation needed|date=October 2007}} Weak, watery solutions of resorcinol (25 to 35 g/kg) are useful in allaying the itching in ].{{Citation needed|date=October 2007}} A 2% solution used as a spray has been used with marked effect in ] and in ].{{Citation needed|date=October 2007}} In the latter disease 0.6 mL of the 2% solution has been given internally. It can be included as an anti-] agent in ] or in ] cosmetics.{{Citation needed|date=October 2007}} It has also been employed in the treatment of ]s in doses of 125 to 250 mg in pills, and is said to be ] and ] in its |
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action.{{Citation needed|date=October 2007}} In large doses it is a ] causing ], ], ], ] and ]. It is also worked up in certain medicated soaps.{{Citation needed|date=October 2007}} Monoacetylresorcinol, C<sub>6</sub>H<sub>4</sub>(OH)(O-COCH<sub>3</sub>), is used under the name of '''euresol'''.{{Citation needed|date=October 2007}} Resorcinol is one of the main active ingredients in products like ] and ]. |
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In presence of ], with twice amount of ], ] creates ] effect on water.<ref name=":0" /> |
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===Chemical=== |
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Resorcinol is also used as a chemical intermediate for the synthesis of pharmaceuticals and other organic compounds. It is used in the production of diazo dyes and plasticizers and as a ] absorber in resins. |
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In addition to electrophilic aromatic addition, resorcinol (and other ]s) undergo nucleophilic substitution via the ] ]. |
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An emerging use of resorcinol is as a template molecule in ]. The -OH groups on resorcinol form ]s to target molecules holding them in the proper orientation for a reaction. Many such reactions are able to be carried out in the ] thereby reducing or eliminating the use of solvents that may be harmful to the environment. (see ]) |
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Nitration with concentrated ] in the presence of cold concentrated ] yields trinitroresorcin (]), an explosive. |
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Resorcinol is an analytical reagent for the qualitative determinaion of ketoses (]). |
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==Occurrence and use== |
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Resorcinol is the starting material for ] molecules and the initiating explosive lead styphnate (Reference: Army TM 9-1300-214, p. 7–12). |
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Derivatives of resorcinol are found in different natural sources. ]s are found in ].<ref>{{Cite journal |last=Suzuki |first=Y |date=1999 |title=Structures of 5-alkylresorcinol-related analogues in rye |url=https://linkinghub.elsevier.com/retrieve/pii/S003194229900196X |journal=Phytochemistry |volume=52 |issue=2 |pages=281–289 |doi=10.1016/S0031-9422(99)00196-X|bibcode=1999PChem..52..281S }}</ref> Polyresorcinols are found as ]s in plants.<ref name=":0">{{Cite journal |last1=Cheng |first1=H. A. |last2=Drinnan |first2=C. T. |last3=Pleshko |first3=N. |last4=Fisher |first4=O. Z. |date=2015-10-21 |title=Pseudotannins Self-assembled into Antioxidant Complexes |journal=] |volume=11 |issue=39 |pages=7783–7791 |doi=10.1039/c5sm01224d |issn=1744-683X |pmid=26313262|pmc=4589535 |bibcode=2015SMat...11.7783C }}</ref> |
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===Adhesives=== |
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Resorcinol reacts with formaldehyde to form a thermoset resin, which can form the basis of an ]. |
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{{main|Resorcinol glue}} |
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Resorcinol is mainly used in the production of resins. As a mixture with ], it condenses with ] to afford ]. Such resins are used as adhesives in the rubber industry and others are used for ].<ref name="Ullmann" /> In relation to its conversion resins with formaldehyde, resorcinol is the starting material for ] rings. |
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===Medical uses=== |
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It is present in over-the-counter topical ] treatments at 2% or less concentration, and in prescription treatments at higher concentrations.<ref>{{cite journal | journal = Clinical and Experimental Dermatology| year = 2010 | volume = 35 | issue = 1 | pages = 36–40 | doi = 10.1111/j.1365-2230.2009.03377.x | pmid = 19549239 | last1 = Boer | first1 = J | last2 = Jemec | first2 = GB | title = Resorcinol peels as a possible self-treatment of painful nodules in hidradenitis suppurativa| s2cid = 1794323 }}</ref> Monoacetylresorcinol, C<sub>6</sub>H<sub>4</sub>(OH)(O–COCH<sub>3</sub>), is used under the name of Euresol.<ref>, ]</ref> It is used in ] with limited evidence showing it can help with resolution of the lesions.<ref name="Wipperman">{{cite journal |last1=Wipperman |first1=J |last2=Bragg |first2=DA |last3=Litzner |first3=B |title=Hidradenitis Suppurativa: Rapid Evidence Review. |journal=American Family Physician |date=1 November 2019 |volume=100 |issue=9 |pages=562–569 |pmid=31674740}}</ref> Resorcinol is one of the active ingredients in products such as ], ], and ]. |
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In the 1950s and early 1960s the British Army used it, in the form of a paste applied directly to the skin. One such place where this treatment was given to soldiers with chronic acne was the Cambridge Military Hospital, Aldershot, England. It was not always successful. |
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] is an ] found in ]. |
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===Chemical uses=== |
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Resorcinol is used as a chemical intermediate for the synthesis of pharmaceuticals and other organic compounds. It is used in the production of ]s and ]s and as a ] absorber in resins. |
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It is an analytical reagent for the qualitative determination of ]s (]). |
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It is the starting material for the initiating explosive ].<ref>"Military Explosives," Department of the Army Technical Manual, TM-9-1300-214 (Washington, D.C.: Department of the Army, September 1984), p. 7-12.</ref> |
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==Related compounds== |
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==Related compounds== |
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], C<sub>12</sub>H<sub>7</sub>NO<sub>4</sub>, obtained by the action of nitrous acid on resorcinol <ref>{{cite journal | first = P | last = Weselsky | coauthors = Benedikt, R | journal = Monats. | year = 1880 | volume = f | pages = 889}}</ref>, forms small dark red crystals possessing a greenish metallic glance. When dissolved in concentrated sulfuric acid and warmed to 210 °C, the solution on pouring into water yields a precipitate of resorufin, C<sub>12</sub>H<sub>7</sub>NO<sub>3</sub>, an oxyphenoxazone, which is insoluble in water, but is readily soluble in hot concentrated hydrochloric acid, and in solutions of caustic alkalis. The alkaline solutions are of a rose-red color and show a cinnabar-red fluorescence. A tetrabromresorufin is used as a dye-stuff under the name of Fluorescent Resorcin Blue. |
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], C<sub>12</sub>H<sub>7</sub>NO<sub>4</sub>, obtained by the action of ] on resorcinol,<ref>{{cite journal | first = P | last = Weselsky |title = Neue Derivate des Resorcins |trans-title=New derivatives of resorcinol |journal = Berichte der Deutschen Chemischen Gesellschaft | year = 1871 | volume = 4 | pages = 32–33 | url = https://books.google.com/books?id=rmkoAAAAYAAJ&pg=PA32 | doi=10.1002/cber.18710040114}}</ref> forms small dark red crystals possessing a greenish metallic glance. When dissolved in concentrated ] and warmed to 210 °C, the solution on pouring into water yields a precipitate of ], C<sub>12</sub>H<sub>7</sub>NO<sub>3</sub>, an ], which is insoluble in water but is readily soluble in hot concentrated ], and in solutions of ]. The alkaline solutions are of a rose-red color and show a cinnabar-red ]. A tetrabromresorufin is used as a ] under the name of Fluorescent Resorcin Blue. |
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Thioresorcinol is obtained by the action of zinc and hydrochloric acid on the chloride of benzene meta-disulfonic acid. It melts at 27 °C and boils at 243 °C. Resorcinol disulfonic acid (HO)<sub>2</sub>C<sub>6</sub>H<sub>2</sub>(HSO3)<sub>2</sub>, is a deliquescent mass obtained by the action of sulfuric acid on resorcin <ref>{{cite journal | first = H | last = Fischer | journal = Monats. | year = 1881 | volume = 2 | pages = 321}}</ref>. It is easily soluble in water and decomposes when heated to 100 °C. |
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] is obtained by the action of ] and ] on ''meta''-benzenedisulfonyl chloride. It melts at 27 °C and boils at 243 °C. Resorcinol disulfonic acid, (HO)<sub>2</sub>C<sub>6</sub>H<sub>2</sub>(HSO<sub>3</sub>)<sub>2</sub>, is a ] mass obtained by the action of ] on resorcin.<ref>{{cite journal | first1 = J. | last1 = Piccard | first2 = A. | last2 = Humbert | year = 1876 | title = Ueber eine Resorcindisulfosäure |trans-title=On a resorcinol disulfonic acid | journal = Berichte der Deutschen Chemischen Gesellschaft | volume = 9 | issue = 2 | pages = 1479–1483 | url = https://books.google.com/books?id=hltBAAAAYAAJ&pg=PA1479 | doi=10.1002/cber.187600902133}}</ref> It is readily soluble in water and ]. |
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Resorcinol is also a common ] that is found in a class of ] agents, some of which (], ganetespib, KW-2478, and onalespib) were in ] {{as of|2014|lc=y}}.<ref name="pmid23312026">{{cite journal |author1=Sidera, K. |author2=Patsavoudi, E. | title = HSP90 inhibitors: current development and potential in cancer therapy. | journal = Recent Patents on Anti-Cancer Drug Discovery| volume = 9 | issue = 1 | pages = 1–20 |date=Jan 2014 | pmid = 23312026 | doi = 10.2174/15748928113089990031 }}</ref><ref name="pmid20055425">{{cite journal |author1=Biamonte, M. A. |author2=Van de Water, R. |author3=Arndt, J. W. |author4=Scannevin, R. H. |author5=Perret, D. |author6=Lee, W.-C. | title = Heat shock protein 90: Inhibitors in clinical trials. | journal = Journal of Medicinal Chemistry| volume = 53 | issue = 1 | pages = 3–17 |date=Jan 2010 | pmid = 20055425 | doi = 10.1021/jm9004708 }}</ref> Part of the resorcinol structure binds to inhibits the ] of ], which is a ] for anticancer treatments.<ref name="pmid23312026"/> |
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==See also== |
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==History, etymology, and nomenclature== |
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Austrian chemist ] (1825–1875) is remembered for his chemical analysis of resorcinol and for his part in the first preparation of resorcinol, along with ], which was published in 1864.<ref>Raj B. Durairaj. ''Resorcinol: Chemistry, Technology and Applications.'' Springer Science & Business Media, 2005 {{ISBN|9783540280903}}</ref>{{rp|10}}<ref>{{cite journal | last1 = McConnell | first1 = Virginia F. | year = 1953 | title = Hlasiwetz and Barth — Pioneers in the structural aspects of plant products | journal = Journal of Chemical Education | volume = 30 | issue = 8| page = 380 | doi = 10.1021/ed030p380 | bibcode = 1953JChEd..30..380M }}</ref> |
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Benzene-1,3-diol is the name recommended by the ] (IUPAC) in its ''1993 Recommendations for the Nomenclature of Organic Chemistry''.<ref>{{cite book | author=Panico, R.; & Powell, W. H. (Eds.) | title=A Guide to IUPAC Nomenclature of Organic Compounds 1992 | location=Oxford | publisher=Blackwell Science | year=1994 | isbn=978-0-632-03488-8}}</ref> |
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Resorcinol is so named because of its derivation from ammoniated resin gum, and for its relation to the chemical ].<ref>H. Hlasiwetz and L. Barth (1864) (On a new substance homologous to orcin), ''Annalen der Chemie'', '''130''' (3) : 354-359. Resorcinol is named on p. 358: ''"Wir nennen den neuen Körper, da wir gefunden haben, dass er auch aus dem Ammoniakgummiharz erhalten werden kann, ''Resorcin'', um an seine Entstehung aus Harzen und seine Beziehung zum Orcin zu erinnern."'' (We name the new substance, since we have found that it can be obtained from ammoniated resin gum, ''resorcin'', in order to recall its creation from resin and its relation to ].)</ref> |
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==Toxicity== |
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Resorcinol has low toxicity, with an {{LD50}} (rats, oral) > 300 mg/kg. It is less toxic than ].<ref name="Ullmann" /> |
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Resorcinol was named a ] under European Union ] in 2022 because of its ] properties.<ref>{{cite news |title=Resorcinol to be added to REACH candidate list after long battle |url=https://chemicalwatch.com/418254/resorcinol-to-be-added-to-reach-candidate-list-after-long-battle |access-date=16 August 2022 |work=Chemical Watch |date=February 10, 2022}}</ref> |
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==References== |
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==References== |
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{{EB1911 |wstitle=Resorcin |volume=23 |pages=183–184}} |
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