2-Chlorobenzoic acid

2-Chlorobenzoic acid
Names
	Preferred IUPAC name 2-Chlorobenzoic acid
	Other names o-Chlorobenzoic acid
Identifiers
CAS Number	118-91-2 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:30793 ;
ChEMBL	ChEMBL115243 ;
ChemSpider	8071 ;
ECHA InfoCard	100.003.897
KEGG	C02357 ;
PubChem CID	8374;
UNII	8P0867193V ;
CompTox Dashboard (EPA)	DTXSID4024771 ;
	InChI InChI=1S/C7H5ClO2/c8-6-4-2-1-3-5(6)7(9)10/h1-4H,(H,9,10) Key: IKCLCGXPQILATA-UHFFFAOYSA-N ; InChI=1/C7H5ClO2/c8-6-4-2-1-3-5(6)7(9)10/h1-4H,(H,9,10) Key: IKCLCGXPQILATA-UHFFFAOYAI;
	SMILES 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
Acidity (pKa)	2.89
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). verify (what is ?) Infobox references

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

^ 1.2-Chlorobenzoic acid; C7H5ClO2; ChemSpider. Chemspider.com (2015). at [1]
^ 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
^ 2.2-Chlorobenzoic acid; C7H5ClO2 - PubChem. Pubchem.ncbi.nlm.nih.gov at [2]
^ ^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.
^ H. T. Clarke and E. R. Taylor (1943). "o-Chlorobenzoic acid". Organic Syntheses; Collected Volumes, vol. 2, p. 135.

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[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]

[Ullmann-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; Collected Volumes, vol. 2, p. 135.

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