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2-Chlorobenzoic acid
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477197744 2-Chlorobenzoic acid - Vect.svg 120px 2-Chlorobenzoic acid o-Chlorobenzoic acid correct chemspider 8071 correct kegg C02357 1/C7H5ClO2/c8-6-4-2-1-3-5(6)7(9)10/h1-4H,(H,9,10) IKCLCGXPQILATA-UHFFFAOYAI correct EBI 115243 correct chemspider 1S/C7H5ClO2/c8-6-4-2-1-3-5(6)7(9)10/h1-4H,(H,9,10) correct chemspider IKCLCGXPQILATA-UHFFFAOYSA-N correct CAS 118-91-2 correct FDA 8P0867193V 8374 correct EBI 30793 O=C(O)c1ccccc1Cl 7 5 1 2 white solid 142 285 2.039 1.2-Chlorobenzoic acid; C7H5ClO2; ChemSpider. Chemspider.com (2015). at 2.89 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. 18382.2-Chlorobenzoic acid; C7H5ClO2 - PubChem. Pubchem.ncbi.nlm.nih.gov at −83.56·10−6 cm3/mol
Oxford MSDS
2-Chlorobenzoic acid is an organic compound with the formula ClC6H4CO2H. It is one of three isomeric chlorobenzoic acids, the one that is the strongest acid. This white solid is used as a precursor to a variety of drugs, food additives, and dyes.Takao Maki, Kazuo Takeda "Benzoic Acid and Derivatives" in Ullmann's Encyclopedia of Industrial Chemistry 2002, Wiley-VCH, Weinheim. 10.1002/14356007.a03_555.
Synthesis and reactions
α,α,α-trichlorotoluene
It is prepared by the oxidation of 2-chlorotoluene. The laboratory scale reaction employs potassium permanganate. o-Chlorobenzoic acid 2 135 cv2p0135 H. T. Clarke and E. R. Taylor 1943 Alternatively it arises by the hydrolysis of α,α,α-trichloro-2-toluene.
The chloride is readily replaced by ammonia to 2-aminobenzoic acid. Similarly, the chloride is displaced by diphenylphosphide, leading to 2-diphenylphosphinobenzoic acid.
At elevated temperature it decarboxylates.
Applications
Known uses include in the synthesis of: Mefenamic acid,((Lednicer, D.)), ((Mitscher, L. A.)) 1977 The organic chemistry of drug synthesis. 1 Wiley 9780471521419 Amsacrine,((Castañer, J.)), ((Paton, D. M.)) Drugs of the Future m-AMSA 5 6 277 1980 http://journals.prous.com/journals/servlet/xmlxsl/pk_journals.xml_summary_pr?p_JournalId=2&p_RefId=154683&p_IsPs=N 0377-8282 10.1358/dof.1980.005.06.154683 28 August 2026 subscription Eproxindine, Diclofenac,((Vardanyan, R. S.)), ((Hruby, V. J.)) 2006 Synthesis of essential drugs Elsevier 1st 9780444521668 Thiethylperazine, Meclofenamic acid,((Castañer, J.)), ((Arrigoni-Martelli, E.)) Drugs of the Future Meclofenamic Acid 3 4 307 1978 http://journals.prous.com/journals/servlet/xmlxsl/pk_journals.xml_summary_pr?p_JournalId=2&p_RefId=277278&p_IsPs=N 0377-8282 10.1358/dof.1978.003.04.277278 28 August 2026 subscription Araprofen, Lucanthone (& thus also ROC 325), Tibric acid, Enfenamic acid, Chlorprothixene (actually 2-iodobenzoic acid according to cited patent).((Lednicer, D.)) 2009 Strategies for organic drug synthesis and design Wiley 2nd 9780470190395 Flufenamic acid 2006 Synthesis of Essential Drugs Elsevier https://linkinghub.elsevier.com/retrieve/pii/B9780444521668X50006 10.1016/B978-0-444-52166-8.X5000-6 9780444521668((Moffett, R. B.)), ((Aspergren, B. D.)) Journal of the American Chemical Society Aminoalkylphenothiazines 82 7 1600–1607 April 1960 https://pubs.acs.org/doi/abs/10.1021/ja01492a022 10.1021/ja01492a022 28 August 2026 subscription ((Carrasco, R.)), ((Pellón, R. F.)), ((Elguero, J.)), ((Goya, P.)), ((Páez, J. A.)) Synthetic Communications The Use of Ultrasound in the Synthesis of N-Thranilic Acids by the Ullmann Goldberg Reaction 19 11–12 2077–2080 July 1989 http://www.tandfonline.com/doi/abs/10.1080/00397918908052600 10.1080/00397918908052600 28 August 2026 subscription
References
Category:Benzoic acids
Category:2-Chlorophenyl compounds