| Revision as of 15:35, 16 February 2012 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Saving copy of the {{chembox}} taken from revid 447521704 of page 2-Chlorobenzoic_acid for the Chem/Drugbox validation project (updated: ''). |
Latest revision as of 15:41, 8 September 2024 edit JWBE (talk | contribs)Extended confirmed users10,122 edits removed Category:Chlorobenzene derivatives; added Category:2-Chlorophenyl compounds using HotCat |
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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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| verifiedrevid = 443313777 |
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| verifiedrevid = 477197744 |
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|ImageFile=2-Chlorobenzoic acid.png |
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| ImageFile=2-Chlorobenzoic acid - Vect.svg |
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|ImageSize=120px |
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| ImageSize=120px |
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|IUPACName=2-chlorobenzoic acid |
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| PIN = 2-Chlorobenzoic acid |
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|OtherNames=''o''-Chlorobenzoic acid |
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| OtherNames=''o''-Chlorobenzoic acid |
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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 = 8071 |
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| ChemSpiderID = 8071 |
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| KEGG_Ref = {{keggcite|correct|kegg}} |
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| KEGG_Ref = {{keggcite|correct|kegg}} |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| CASNo=118-91-2 |
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| CASNo=118-91-2 |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| PubChem= 8374 |
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| UNII = 8P0867193V |
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| ChEBI_Ref = {{ebicite|correct|EBI}} |
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| PubChem= 8374 |
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| ChEBI_Ref = {{ebicite|correct|EBI}} |
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| ChEBI = 30793 |
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| ChEBI = 30793 |
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| SMILES = O=C(O)c1ccccc1Cl |
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| SMILES = O=C(O)c1ccccc1Cl |
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|Section2={{Chembox Properties |
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|Section2={{Chembox Properties |
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| C = 7 | H = 5 | Cl = 1 | O = 2 |
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| C=7 | H=5 | Cl=1 | O=2 |
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| Appearance=light brown solid |
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| Appearance=white solid |
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| Density= |
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| Density= |
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| MeltingPtC=142 |
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| MeltingPtC=142 |
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| BoilingPtC=285 |
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| BoilingPtC=285 |
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| LogP = 2.039 <ref>1.2-Chlorobenzoic acid; C7H5ClO2; ChemSpider. Chemspider.com (2015). at </ref> |
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| Solubility= |
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| pKa = 2.89 <ref>Clayton, G. D. and F. E. Clayton (eds.). Patty's Industrial Hygiene and Toxicology: Volume 2A, 2B, 2C: Toxicology. 3rd ed. New York: John Wiley Sons, 1981-1982., p. 1838</ref> <ref>2.2-Chlorobenzoic acid; C7H5ClO2 - PubChem. Pubchem.ncbi.nlm.nih.gov at </ref> |
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| Solubility= |
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| MagSus = -83.56·10<sup>−6</sup> cm<sup>3</sup>/mol |
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|Section3={{Chembox Hazards |
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|Section3={{Chembox Hazards |
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| ExternalMSDS = |
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| ExternalSDS = |
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| FlashPt= |
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| FlashPt= |
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| AutoignitionPt = |
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'''2-Chlorobenzoic acid''' is an ] with the formula ClC<sub>6</sub>H<sub>4</sub>CO<sub>2</sub>H. It is one of three ] ]s, the one that is the strongest acid. This white solid is used as a precursor to a variety of drugs, food additives, and dyes.<ref name=Ullmann>Takao Maki, Kazuo Takeda "Benzoic Acid and Derivatives" in Ullmann's Encyclopedia of Industrial Chemistry 2002, Wiley-VCH, Weinheim. {{doi|10.1002/14356007.a03_555}}.</ref> |
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==Synthesis and reactions== |
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{{See also|α,α,α-trichlorotoluene}} |
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It is prepared by the ] of 2-]. The laboratory scale reaction employs ].<ref>{{OrgSynth | title = ''o''-Chlorobenzoic acid | collvol = 2 | collvolpages = 135 | prep = cv2p0135 | author = H. T. Clarke and E. R. Taylor | year = 1943}}</ref> Alternatively it arises by the hydrolysis of α,α,α-trichloro-2-toluene. |
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The chloride is readily replaced by ammonia to ]. Similarly, the chloride is displaced by ], leading to ]. |
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At elevated temperature it ]s.<ref name=Ullmann/> |
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==References== |
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<references/> |
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{{DEFAULTSORT:Chlorobenzoic acid, 2-}} |
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] |
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] |
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{{organohalide-stub}} |