2-Chlorobenzoic acid

2-Chlorobenzoic acid
Names
Preferred IUPAC name
2-Chlorobenzoic acid
Other names
o-Chlorobenzoic acid
Identifiers
CAS Number
  • 118-91-2 checkY
3D model (JSmol)
  • Interactive image
ChEBI
  • CHEBI:30793 checkY
ChEMBL
  • ChEMBL115243 checkY
ChemSpider
  • 8071 checkY
ECHA InfoCard 100.003.897 Edit this at Wikidata
KEGG
  • C02357 checkY
PubChem CID
  • 8374
UNII
  • 8P0867193V checkY
CompTox Dashboard (EPA)
  • DTXSID4024771 Edit this at Wikidata
InChI
  • 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
Chemical formula
 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]
Magnetic susceptibility (χ)
 -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
Chemical compound

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. ^ a b 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; Collected Volumes, vol. 2, p. 135.
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