| Revision as of 09:28, 5 December 2011 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Saving copy of the {{chembox}} taken from revid 462328413 of page Benzoin for the Chem/Drugbox validation project (updated: ''). |
Latest revision as of 01:21, 25 December 2023 edit 1234qwer1234qwer4 (talk | contribs)Extended confirmed users, Page movers197,958 edits added Category:Substances discovered in the 19th century using HotCat |
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{{distinguish|Benzoin (resin)}}{{other|Benzoin (disambiguation)}} |
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{{ambox | text = This page contains a copy of the infobox ({{tl|chembox}}) taken from revid of page ] with values updated to verified values.}} |
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{{chembox |
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{{Chembox |
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| Name = Benzoin |
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| verifiedrevid = 443418104 |
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| Watchedfields = changed |
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| verifiedrevid = 464186825 |
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| ImageFile_Ref = {{chemboximage|correct|??}} |
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| ImageFile_Ref = {{chemboximage|correct|??}} |
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| ImageFile = Benzoin.png |
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| ImageFile = Benzoin.svg |
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| ImageFile1 = Benzoin-3D-balls.png |
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| ImageFile1 = Benzoin-3D-balls.png |
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| IUPACName = 2-hydroxy-1,2-di(phenyl)ethanone |
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| PIN = 2-Hydroxy-1,2-diphenylethan-1-one |
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| OtherNames = 2-hydroxy-2-phenylacetophenone, 2-hydroxy-1,2-diphenylethanone, desyl alcohol, bitter almond oil camphor |
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| OtherNames = 2-Hydroxy-2-phenylacetophenone<br />2-Hydroxy-1,2-diphenylethanone<br />Desyl alcohol<br />Bitter almond oil camphor |
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| Section1 = {{Chembox Identifiers |
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|Section1={{Chembox Identifiers |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID = 8093 |
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| ChemSpiderID = 8093 |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| ChEMBL_Ref = {{ebicite|correct|EBI}} |
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| ChEMBL_Ref = {{ebicite|correct|EBI}} |
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| ChEMBL = 190677 |
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| ChEMBL = 190677 |
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| Beilstein = 391839 |
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| 3DMet = B00286 |
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| RTECS = DI1590000 |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChI = 1S/C14H12O2/c15-13(11-7-3-1-4-8-11)14(16)12-9-5-2-6-10-12/h1-10,13,15H |
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| StdInChI = 1S/C14H12O2/c15-13(11-7-3-1-4-8-11)14(16)12-9-5-2-6-10-12/h1-10,13,15H |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| CASNo = 119-53-9 |
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| CASNo = 119-53-9 |
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| PubChem = 8400 |
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| PubChem = 8400 |
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| ChEBI_Ref = {{ebicite|correct|EBI}} |
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| ChEBI_Ref = {{ebicite|correct|EBI}} |
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| ChEBI = 17682 |
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| ChEBI = 17682 |
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| SMILES = O=C(c1ccccc1)C(O)c2ccccc2 |
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| SMILES = O=C(c1ccccc1)C(O)c2ccccc2 |
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}} |
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|Section2={{Chembox Properties |
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| C=14 | H=12 | O=2 |
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| Appearance = Off-white crystals |
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| Density = 1.310 g/cm<sup>3</sup> (20 °C)<ref name="crc97">{{cite book | author=William M. Haynes | title=CRC Handbook of Chemistry and Physics | edition=97th | year=2016 | publisher=CRC Press | location=Boca Raton | isbn=978-1-4987-5429-3 | page=3-40 | url=https://books.google.com/books?id=VVezDAAAQBAJ}}</ref> |
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| MeltingPtC = 135 to 139<ref name="crc97"/> |
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| MeltingPt_notes = |
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| BoilingPtC = 330 to 356<ref name="crc97"/> |
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| BoilingPt_notes = |
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| Solubility = Slightly soluble |
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| Solvent1 = ethanol |
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| Solubility1 = Very good<ref name="crc97"/> |
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| Solvent2 = ether |
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| Solubility2 = Slightly soluble |
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| Solvent3 = chlorine |
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| Solubility3 = Soluble |
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| Solvent4 = chloroform |
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| Solubility4 = Very good<ref name="crc97"/> |
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}} |
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|Section3={{Chembox Hazards |
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| LD50 = 10.000 mg/kg |
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| MainHazards = |
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| FlashPt = |
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| AutoignitionPt = |
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| NFPA-H = 1 |
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| NFPA-F = 1 |
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| NFPA-R = 0 |
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| NFPA-S = |
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| HPhrases = {{H-phrases|412}} |
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| PPhrases = {{P-phrases|273|501}} |
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}} |
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}} |
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}} |
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| Section2 = {{Chembox Properties |
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'''Benzoin''' ({{IPAc-en|ˈ|b|ɛ|n|z|oʊ|.|ᵻ|n}} or {{IPAc-en|-|ɔɪ|n}}) is an ] with the formula PhCH(OH)C(O)Ph. It is a ] attached to two ] groups. It appears as off-white crystals, with a light ]-like odor. Benzoin is synthesized from ] in the ]. It is chiral and it exists as a pair of enantiomers: (''R'')-benzoin and (''S'')-benzoin. |
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|C=14|H=12|O=2 |
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| Appearance = off-white crystals |
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Benzoin is ''not'' a constituent of ] obtained from the ] ''(Styrax)'' or ]. The main component in these natural products is ]. |
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| Density = 1.31 g/cm<sup>3</sup> |
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| MeltingPt = 132-137 °C |
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==History== |
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| BoilingPt = 344 °C |
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Benzoin was first reported in 1832 by ] and ] during their research on ], which is ] with traces of ].<ref>{{cite journal |
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| Solubility = Slightly Soluble |
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| title = Untersuchungen über das Radikal der Benzoesäure |
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| Solvent = ] |
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| author = Wöhler, Liebig |
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| SolubleOther = Slightly Soluble |
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| journal = Annalen der Pharmacie |
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| Solvent = ] |
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| volume = 3 |
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| SolubleOther = Soluble |
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| Solvent = ] |
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| issue = 3 |
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| pages = 249–282 |
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| SolubleOther = Slightly Soluble |
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| year = 1832 |
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| Solvent = ] |
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| url = |
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| SolubleOther = Soluble |
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| doi = 10.1002/jlac.18320030302 |
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| last2 = Liebig | hdl = 2027/hvd.hxdg3f |
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| hdl-access = free |
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}}</ref> The catalytic synthesis by the ] was improved by ] during his time with Liebig.<ref>{{cite journal |
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| title = Beiträge zur Kenntniss einiger Verbindungen aus der Benzoylreihe |
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| author = N. Zinin |
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| journal = Annalen der Pharmacie |
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| volume = 31 |
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| issue = 3 |
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| pages = 329–332 |
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| year = 1839 |
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| url = https://zenodo.org/record/1426941 |
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| doi = 10.1002/jlac.18390310312 |
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| access-date = 2020-09-10 |
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| archive-date = 2022-07-09 |
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| archive-url = https://web.archive.org/web/20220709093441/https://zenodo.org/record/1426941 |
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| url-status = live |
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}}</ref><ref>{{cite journal |
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| title = Ueber einige Zersetzungsprodukte des Bittermandelöls |
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| author = N. Zinin |
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| journal = Annalen der Pharmacie |
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| volume = 34 |
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| issue = 2 |
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| pages = 186–192 |
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| year = 1840 |
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| url = https://zenodo.org/record/1426951 |
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| doi = 10.1002/jlac.18400340205 |
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| access-date = 2019-06-30 |
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| archive-date = 2022-07-09 |
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| archive-url = https://web.archive.org/web/20220709093441/https://zenodo.org/record/1426951 |
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| url-status = live |
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}}</ref> |
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==Uses== |
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The main use of benzoin is as a precursor to ], which is used as a ].<ref name=Ullmann>Hardo Siegel, Manfred Eggersdorfer "Ketones" in Ullmann's Encyclopedia of Industrial Chemistry Wiley-VCH, 2002 by Wiley-VCH, Wienheim. {{doi|10.1002/14356007.a15_077}}</ref><ref>{{Cite book |last=Nakamura |first=Kenichiro |url=https://www.worldcat.org/oclc/884012539 |title=Photopolymers : photoresist materials, processes, and applications |date=2015 |isbn=978-1-4665-1731-8 |location=Boca Raton, FL |oclc=884012539}}</ref> The conversion proceeds by ] using copper(II),<ref>{{OrgSynth | author = Clarke, H. T. |author2=Dreger.E. E. | title = Benzil | collvol = 1 | collvolpages = 87 | year = 1941 | prep = cv1p0087}}</ref> ], or ]. In one study, this reaction is carried out with atmospheric oxygen and basic ] in ].<ref>{{cite journal|title=A very simple and chemoselective air oxidation of benzoins to benzils using alumina|author1=Konstantinos Skobridis|author2=Vassiliki Theodorou|author3=Edwin Weber|journal=]|volume=06-1798JP|pages=102–106|year=2006|url=http://www.arkat-usa.org/ark/journal/2006/I10_General/1798/06-1798JP%20as%20published%20mainmanuscript.asp}}{{Dead link|date=June 2019 |bot=InternetArchiveBot |fix-attempted=yes }}</ref> |
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Benzoin also sees wide spread use in ] formulations, where it acts as a degassing agent during the ] stage. This action prevents surface defects such as 'pinholing'.<ref>{{cite journal |last1=Maxwell |first1=B.E |last2=Wilson |first2=R.C |last3=Taylor |first3=H.A |last4=Williams |first4=D.E |last5=Farnham |first5=W |last6=Tria |first6=J |title=Understanding benzoin's mode of action in powder coatings |journal=Progress in Organic Coatings |date=November 2001 |volume=43 |issue=1–3 |pages=158–166 |doi=10.1016/S0300-9440(01)00181-3}}</ref><ref>{{cite journal |last1=Jahromi |first1=Shahab |last2=Mostert |first2=Ben |last3=Derks |first3=Andreas |last4=Koldijk |first4=Fokelien |title=Mechanism of action of benzoin as a degassing agent in powder coatings |journal=Progress in Organic Coatings |date=December 2003 |volume=48 |issue=2–4 |pages=183–193 |doi=10.1016/S0300-9440(03)00096-1}}</ref> |
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Benzoin can be used in the preparation of several pharmaceutical drugs including ], ], and ].<ref>{{US patent|2242775}}</ref> |
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==Preparation== |
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Benzoin is prepared from ] via the ].<ref> |
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{{ |
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OrgSynth |
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| author = Roger Adams |
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| author2 = C. S. Marvel |
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| title = Benzoin |
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| volume = 1 |
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| pages = 33 |
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| year = 1921 |
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| collvol = 1 |
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| collvolpages = 94 |
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| collyear = 1941 |
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| prep = CV1P0094 |
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}} |
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}} |
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</ref> |
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| Section3 = {{Chembox Hazards |
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| MainHazards = |
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==References== |
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| FlashPt = |
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{{reflist}} |
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| Autoignition = |
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| NFPA-H = 2 |
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==External links== |
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| NFPA-F = 1 |
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* , ''Organic Syntheses'', Coll. Vol. 1, p. 94 (1941); Vol. 1, p. 33 (1921) |
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| NFPA-R = 0 |
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| NFPA-O = |
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{{Authority control}} |
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}} |
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}} |
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] |
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] |
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] |