Cyclohexanecarboxylic acid

Cyclohexanecarboxylic acid
Names
Preferred IUPAC name
Cyclohexanecarboxylic acid
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.002.465 Edit this at Wikidata
UNII
  • InChI=1S/C7H12O2/c8-7(9)6-4-2-1-3-5-6/h6H,1-5H2,(H,8,9)
    Key: NZNMSOFKMUBTKW-UHFFFAOYSA-N
  • InChI=1/C7H12O2/c8-7(9)6-4-2-1-3-5-6/h6H,1-5H2,(H,8,9)
    Key: NZNMSOFKMUBTKW-UHFFFAOYAH
  • O=C(O)C1CCCCC1
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).

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.

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.

Cyclohexanecarboxylic acid exhibits the reactions typical of carboxylic acids, including its conversion to the acid chloride cyclohexanecarbonyl chloride using thionyl chloride or oxalyl chloride and to various other acyl derivatives either directly or by way of the acyl halide.

Esterification to ethyl cyclohexanoate [3289-28-9] (aka Esterly™) described as "Ripe fruit, apple, strawberry." (synthesis:).

Biochemistry

Cyclohexanecarboxylic acid is a product in the metabolism of benzoic acid in certain microorganisms. In rat models, cyclohexanecarboxylic acid was found to have anti-convulsant activity in a manner similar to valproic acid.

References

  1. ↑ Nomenclature of Organic Chemistry : IUPAC Recommendations and Preferred Names 2013 (Blue Book). Cambridge: The Royal Society of Chemistry. 2014. pp. 303, 639. doi:10.1039/9781849733069-00648. ISBN 978-0-85404-182-4.
  2. 1 2 Maki, Takao; Takeda, Kazuo. "Benzoic Acid and Derivatives". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a03_555. ISBN 978-3-527-30673-2..
  3. ↑ Cope, Arthur C.; Ciganek, Engelbert (1959). "N,N-Dimethylcyclohexylmethylamine". Organic Syntheses. 39: 19. doi:10.15227/orgsyn.039.0019.
  4. ↑ Spessard, Gary O.; Chan, Wan Kit; Masamune, S. (1983). "Preparation of thiol esters: S-tert-butyl cyclohexanecarbothioate and S-tert-butyl 3α,7α,12α-trihydroxy-5β-cholane-24-thioate". Organic Syntheses. 61: 134. doi:10.15227/orgsyn.061.0134.
  5. ↑ Lee, D. (10 July 2013). "Preparation of a Sulfonated Carbonaceous Material from Lignosulfonate and Its Usefulness as an Esterification Catalyst". Molecules. 18 (7): 8168–8180. doi:10.3390/molecules18078168. ISSN 1420-3049. PMC 6269820. PMID 23846757.
  6. ↑ Elshahed, M. S.; Bhupathiraju, V. K.; Wofford, N. Q.; Nanny, M. A.; McInerney, M. J. (2001). "Metabolism of benzoate, cyclohex-1-ene carboxylate, and cyclohexane carboxylate by "Syntrophus aciditrophicus" strain SB in syntrophic association with H2-using microorganisms". Applied and Environmental Microbiology. 67 (4): 1728–1738. doi:10.1128/AEM.67.4.1728-1738.2001. PMC 92791. PMID 11282627.
  7. ↑ Liu, M. J.; Pollack, G. M. (1994). "Pharmacokinetics and pharmacodynamics of valproate analogues in rats. IV. Anticonvulsant action and neurotoxicity of octanoic acid, cyclohexanecarboxylic acid, and 1-methyl-1-cyclohexanecarboxylic acid". Epilepsia. 35 (1): 234–243. doi:10.1111/j.1528-1157.1994.tb02939.x. PMID 8112253.