2-Chlorobenzoic acid

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]

2-Chlorobenzoic acid
Names
Preferred IUPAC name
2-Chlorobenzoic acid
Other names
o-Chlorobenzoic acid
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.003.897
KEGG
UNII
  • InChI=1S/C7H5ClO2/c8-6-4-2-1-3-5(6)7(9)10/h1-4H,(H,9,10) checkY
    Key: IKCLCGXPQILATA-UHFFFAOYSA-N checkY
  • InChI=1/C7H5ClO2/c8-6-4-2-1-3-5(6)7(9)10/h1-4H,(H,9,10)
    Key: IKCLCGXPQILATA-UHFFFAOYAI
  • O=C(O)c1ccccc1Cl
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 (SDS) 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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Infobox references

Synthesis and reactions
See also: α,α,α-trichlorotoluene

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
  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
  4. 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.; Collective Volume, vol. 2, p. 135
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