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    2-Chlorobenzoic acid

    Topic: Chemistry

     From Handwiki - Reading time: 2 min
    2-Chlorobenzoic acid
    2-Chlorobenzoic acid - Vect.svg
    Names
    Preferred IUPAC name
    2-Chlorobenzoic acid
    Other names
    o-Chlorobenzoic acid
    Identifiers
    3D model (JSmol)
    ChEBI
    ChEMBL
    ChemSpider
    KEGG
    UNII
    Properties
    C7H5ClO2
    Molar mass 156.57 g·mol−1
    Appearance white solid
    Melting point 142 °C (288 °F; 415 K)
    Boiling point 285 °C (545 °F; 558 K)
    log P 2.039 [1]
    Acidity (pKa) 2.89 [2] [3]
    -83.56·10−6 cm3/mol
    Hazards
    Safety data sheet Oxford MSDS
    Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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    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.[4]

    Synthesis and reactions

    It is prepared by the oxidation of 2-chlorotoluene. The laboratory scale reaction employs potassium permanganate.[5] 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.[4]

    References

    1. ↑ 1.2-Chlorobenzoic acid; C7H5ClO2; ChemSpider. Chemspider.com (2015). at [1]
    2. ↑ 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
    3. ↑ 2.2-Chlorobenzoic acid; C7H5ClO2 - PubChem. Pubchem.ncbi.nlm.nih.gov at [2]
    4. ↑ 4.0 4.1 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.
    5. ↑ H. T. Clarke and E. R. Taylor (1943). "o-Chlorobenzoic acid". Organic Syntheses. http://www.orgsyn.org/demo.aspx?prep=cv2p0135. ; Collective Volume, 2, pp. 135 



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