Revision as of 16:10, 16 February 2012 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Saving copy of the {{chembox}} taken from revid 476964713 of page 1,2-Dichlorobenzene for the Chem/Drugbox validation project (updated: ''). |
Latest revision as of 21:29, 10 February 2024 edit Michael7604 (talk | contribs)Extended confirmed users8,895 edits is an aryl chloride and |
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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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| Verifiedfields = changed |
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|Verifiedfields = changed |
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|Watchedfields = changed |
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| verifiedrevid = 456361325 |
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|verifiedrevid = 477203514 |
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| Reference=<ref>'']'', 11th Edition, '''3044'''</ref> |
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|Reference = <ref>'']'', 11th Edition, '''3044'''</ref> |
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| Name = 1,2-Dichlorobenzene |
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| ImageFileL1 = 1,2-Dichlorobenzene.svg |
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|Name = 1,2-Dichlorobenzene |
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|ImageFile1 = O-Dichlorobenzene-2D-skeletal.svg |
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| ImageSizeL1 = 120px |
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| ImageNameL1 = 1,2-Dichlorobenzene |
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|ImageName1 = Skeletal structure of 1,2-Dichlorobenzene |
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|ImageSize1 = 150px |
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| ImageFileR1 = Ortho-dichlorobenzene-3D-balls.png |
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|ImageFileL2 = 1,2-Dichlorobenzene-Mercury-3D-bs.png |
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| ImageSizeR1 = 120px |
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| ImageNameR1 = Ball-and-stick model of 1,2-dichlorobenzene |
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|ImageNameL2 = Ball-and-stick model of the 1,2-dichlorobenzene molecule |
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|ImageSizeL2 = 150px |
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| IUPACName = 1,2-Dichlorobenzene |
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| OtherNames = ''ortho''-Dichlorobenzene,''o''-Dichlorbenzene, odcb |
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|ImageFileR2 = 1,2-Dichlorobenzene-Mercury-3D-sf.png |
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|ImageNameR2 = Space-filling model of the 1,2-dichlorobenzene molecule |
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| Section1 = {{Chembox Identifiers |
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|ImageSizeR2 = 150px |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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|PIN = 1,2-Dichlorobenzene |
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| ChEBI_Ref = {{ebicite|correct|EBI}} |
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|OtherNames = ''ortho''-Dichlorobenzene, ''o''-Dichlorobenzene, odcb, ''o''-Dichlorobenzol |
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| ChEBI = 35290 |
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|Section1={{Chembox Identifiers |
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| ChemSpiderID = 13837988 |
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|PubChem = 7239 |
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| KEGG_Ref = {{keggcite|correct|kegg}} |
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|ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| KEGG = C14328 |
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|ChEBI_Ref = {{ebicite|correct|EBI}} |
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| InChI = 1/C6H4Cl2/c7-5-3-1-2-4-6(5)8/h1-4H |
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|ChEBI = 35290 |
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| InChIKey = RFFLAFLAYFXFSW-UHFFFAOYAE |
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|ChemSpiderID = 13837988 |
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| SMILES1 = c1ccc(c(c1)Cl)Cl |
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| ChEMBL_Ref = {{ebicite|changed|EBI}} |
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|KEGG_Ref = {{keggcite|correct|kegg}} |
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| ChEMBL = 298461 |
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|KEGG = C14328 |
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|InChI = 1/C6H4Cl2/c7-5-3-1-2-4-6(5)8/h1-4H |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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|InChIKey = RFFLAFLAYFXFSW-UHFFFAOYAE |
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| StdInChI = 1S/C6H4Cl2/c7-5-3-1-2-4-6(5)8/h1-4H |
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|SMILES1 = c1ccc(c(c1)Cl)Cl |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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|ChEMBL_Ref = {{ebicite|correct|EBI}} |
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| StdInChIKey = RFFLAFLAYFXFSW-UHFFFAOYSA-N |
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| CASNo = 95-50-1 |
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|ChEMBL = 298461 |
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|StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| EC No = 202-425-9 |
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|StdInChI = 1S/C6H4Cl2/c7-5-3-1-2-4-6(5)8/h1-4H |
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| Annex No = 602-034-00-7 |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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|StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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|StdInChIKey = RFFLAFLAYFXFSW-UHFFFAOYSA-N |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| UNII = 6PJ93I88XL |
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|CASNo = 95-50-1 |
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|EC_number = 202-425-9 |
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| SMILES = c1ccc(c(c1)Cl)Cl |
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|CASNo_Ref = {{cascite|correct|CAS}} |
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|UNII_Ref = {{fdacite|correct|FDA}} |
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|UNII = 6PJ93I88XL |
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|SMILES = c1ccc(c(c1)Cl)Cl |
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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>4</sub>Cl<sub>2</sub> |
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|Formula = C{{sub|6}}H{{sub|4}}Cl{{sub|2}} |
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|Appearance = colourless liquid |
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| MolarMass = 147.01 g/mol |
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|Odor = Naphthalene-like |
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| Density = 1.30 g/cm³ |
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|MolarMass = 147.01 g/mol |
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| MeltingPtC = -17.03 |
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|Density = 1.30 g/cm{{sup|3}} |
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| BoilingPtC = 180.5 |
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|MeltingPtC = -17.03 |
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}} |
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|BoilingPtC = 180.19 |
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| Section7 = {{Chembox Hazards |
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|BoilingPt_ref = <ref>{{Cite journal|last1=Roháč|first1=Vladislav|last2=Růžička|first2=Vlastimil|last3=Růžička|first3=Květoslav|last4=Aim|first4=Karel|date=September 1998|title=Measurements of Saturated Vapor Pressure above the Liquid Phase for Isomeric Dichlorobenzenes and 1,2,4-Trichlorobenzene |journal=Journal of Chemical & Engineering Data|language=en |volume=43|issue=5|pages=770–775|doi=10.1021/je9701442|issn=0021-9568}}</ref> |
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| FlashPt = 66 °C |
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|Solubility = 0.01%<ref name=PGCH/> |
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| SkinHazard = Causes skin irritation |
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|VaporPressure = 1 mmHg (20°C) |
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| EyeHazard = Causes eye irritation |
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|Viscosity = 1.0656 (20 °C) |
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| InhalationHazard = Causes respiratory tract irritation |
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|MagSus = -84.26·10{{sup|−6}} cm{{sup|3}}/mol |
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| IngestionHazard = Toxic if swallowed |
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|RefractIndex = 1.54920 |
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| ExternalMSDS = http://www.sigmaaldrich.com/catalog/DisplayMSDSContent.do |
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}} |
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}} |
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}} |
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|Section3={{Chembox Hazards |
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|FlashPtC = 66 |
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|SkinHazard = Causes skin irritation |
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|EyeHazard = Causes eye irritation |
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|InhalationHazard = Causes respiratory tract irritation |
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|IngestionHazard = Mildly toxic |
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|ExternalSDS = |
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|PEL = C 50 ppm (300 mg/m{{sup|3}})<ref name=PGCH>{{PGCH|0189}}</ref> |
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|ExploLimits = 2.2%-9.2%<ref name=PGCH/> |
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|IDLH = 200 ppm<ref name=PGCH/> |
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|LD50 = 500 mg/kg (oral, rat, rabbit)<br/> 200 mg/kg (oral, guinea pig)<br/>436 mg/kg (oral, mouse)<ref name=IDLH>{{cite web |url = https://www.cdc.gov/niosh/idlh/95501.html |title = ''o''-Dichlorobenzene |publisher = National Institute for Occupational Safety and Health (NIOSH) |date = 4 December 2014 |access-date = 6 March 2015}}</ref> |
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|REL = C 50 ppm (300 mg/m{{sup|3}})<ref name=PGCH/> |
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|LCLo = 1000 ppm (guinea pig, 20 hr)<br/>800 ppm (guinea pig, 24 hr)<br/>821 ppm (rat, 7 hr)<ref name=IDLH/> |
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}} |
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|Section4={{Chembox Related |
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| OtherCompounds = ]<br/>] |
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}} |
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}} |
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'''1,2-Dichlorobenzene''', or '''orthodichlorobenzene''' ('''ODCB'''), is an ] and isomer of ] with the formula C{{sub|6}}H{{sub|4}}Cl{{sub|2}}. This colourless liquid is poorly soluble in water but miscible with most organic solvents. It is a derivative of ], consisting of two adjacent ] atoms. |
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It is mainly used as a ] in the synthesis of ]s, as a preferred solvent for dissolving and working with ]s, as an ], and in softening and removing carbon-based contamination on metal surfaces. |
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==Production and uses== |
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1,2-Dichlorobenzene is obtained as a side-product of the production of ]: |
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:{{chem|C|6|H|5|Cl}} + {{chem|Cl|2}} → {{chem|C|6|H|4|Cl|2}} + HCl |
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The reaction also affords the 1,4- and small amounts of the 1,3-isomer. The 1,4- isomer is preferred over the 1,2- isomer due to ]. The ] is uncommon because it is a meta- compound, while chlorine, like all halogens, is an ] director in terms of ]. |
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It is mainly used as a precursor to ], an intermediate in the synthesis of ]s.<ref name=Booth>Gerald Booth (2007). "Nitro Compounds, Aromatic" in ''Ullmann's Encyclopedia of Industrial Chemistry'' Wiley-VCH, Weinheim, 2005.</ref> In terms of niche applications, 1,2-dichlorobenzene is a versatile, high-boiling solvent. It is a preferred solvent for dissolving and working with ]s. It is an ] for termites and locust borers, historically used by the ] to combat widespread bark beetle outbreaks.<ref>{{cite web|url=https://www.youtube.com/watch?v=axs2jR2HC6I |archive-url=https://ghostarchive.org/varchive/youtube/20211221/axs2jR2HC6I |archive-date=2021-12-21 |url-status=live|title=Battle of the Beetles|date=25 July 2011|access-date=22 April 2018|via=YouTube}}{{cbignore}}</ref> |
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1,2-Dichlorobenzene is also used in softening and removing carbon-based contamination on metal surfaces.<ref>Technical Order 2J-1-13</ref> |
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==Safety== |
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Data from human exposure to 1,2-dichlorobenzene shows that concentrations of 100 ppm have been reported to cause sporadic irritation of the eyes and respiratory tract.<ref>{{cite web|url=https://www.cdc.gov/niosh/idlh/95501.html|title=CDC - Immediately Dangerous to Life or Health Concentrations (IDLH): o-Dichlorobenzene - NIOSH Publications and Products|date=16 November 2017|website=www.cdc.gov|access-date=22 April 2018}}</ref> The ] and the ] have set occupational exposure limits at a ceiling of 50 ppm, over an eight-hour workday.<ref>{{cite web|url=https://www.cdc.gov/niosh/npg/npgd0189.html|title=CDC - NIOSH Pocket Guide to Chemical Hazards -o-Dichlorobenzene|website=www.cdc.gov|access-date=22 April 2018}}</ref> |
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==See also== |
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*]—different numbers of chlorine substituents and isomeric forms |
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==References== |
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<references/> |
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{{Insecticides}} |
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{{DEFAULTSORT:Dichlorobenzene, 1, 2-}} |
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] |
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] |
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] |
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] |