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]
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| Names | |
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| Preferred IUPAC name
2-Chlorobenzoic acid | |
| Other names
o-Chlorobenzoic acid | |
| Identifiers | |
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| ECHA InfoCard | 100.003.897 
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CompTox Dashboard (EPA) |
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| 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] |
| -83.56·10−6cm3/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). | |
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]
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