Cyclohexanecarboxylic acid
Chemical compound
From Wikipedia, the free encyclopedia
Cyclohexanecarboxylic acid is the organic compound with the formula C6H11CO2H or C6H11COOH. It is the carboxylic acid of cyclohexane. It is a colorless oil that crystallizes near room temperature.[2]
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| Names | |
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| Preferred IUPAC name
Cyclohexanecarboxylic acid[1] | |
| Identifiers | |
3D model (JSmol) |
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| ChEBI | |
| ChemSpider | |
| ECHA InfoCard | 100.002.465 |
PubChem CID |
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| UNII | |
CompTox Dashboard (EPA) |
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| Properties | |
| C7H12O2 | |
| Molar mass | 128.171 g·mol−1 |
| Appearance | white solid |
| Density | 1.0274 g/cm3 |
| Melting point | 30–31 °C (86–88 °F; 303–304 K) |
| Boiling point | 232–234 °C (450–453 °F; 505–507 K) |
| −83.24·10−6 cm3/mol | |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Preparation and reactions
It is prepared by hydrogenation of benzoic acid.
Cyclohexanecarboxylic acid is a precursor to the nylon-6 precursor caprolactam via its reaction with nitrosylsulfuric acid. It can also be oxidized to cyclohexene.[2]
Cyclohexanecarboxylic acid exhibits the reactions typical of carboxylic acids, including its conversion to the acid chloride cyclohexanecarbonyl chloride using thionyl chloride[3] or oxalyl chloride[4] and to various other acyl derivatives either directly or by way of the acyl halide.
Biochemistry
Cyclohexanecarboxylic acid is a product in the metabolism of benzoic acid in certain microorganisms.[5] In rat models, cyclohexanecarboxylic acid was found to have anti-convulsant activity in a manner similar to valproic acid.[6]
Related compounds
- 1,4-Cyclohexanedicarboxylic acid
- Quinic acid, a polyhydroxy derivative
- Methyl cyclohexanecarboxylate, the methyl ester
External links
- Cyclohexanecarboxylic+Acids at the U.S. National Library of Medicine Medical Subject Headings (MeSH)