Cyclohexanecarboxylic acid

Cyclohexanecarboxylic acid
Names
	Preferred IUPAC name Cyclohexanecarboxylic acid
Identifiers
CAS Number	98-89-5 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:36096;
ChemSpider	7135;
ECHA InfoCard	100.002.465
PubChem CID	7413;
UNII	H9VKD9VL18 ;
CompTox Dashboard (EPA)	DTXSID8059180 ;
	InChI 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;
	SMILES O=C(O)C1CCCCC1;
Properties
Chemical formula	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)
Magnetic susceptibility (χ)	-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). Infobox references

Cyclohexanecarboxylic acid is the organic compound with the formula C₆H₁₁CO₂H. It is the carboxylic acid of cyclohexane. It is a colorless oil that crystallizes near room temperature.^[2]

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.^[3]^[4]

Related compounds

Derivatives related to cyclohexanecarboxylic acid include:

External links

Cyclohexanecarboxylic Acids at the U.S. National Library of Medicine Medical Subject Headings (MeSH)

References

^ 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.
^ ^a ^b Maki, Takao; Takeda, Kazuo. "Benzoic Acid and Derivatives". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a03_555. ISBN 978-3527306732..
^ Turro, Nicholas J.; Leermakers, Peter A.; Vesley, George F. (1967). "Cyclohexylidenecyclohexane". Org. Synth. 47: 34. doi:10.15227/orgsyn.047.0034.
^ Cope, Arthur C.; Ciganek, Engelbert (1959). "N,N-Dimethylcyclohexylmethylamine". Organic Syntheses. 39: 19. doi:10.15227/orgsyn.039.0019.

[iupac2013-1] 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.

[Ullmann-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 978-3527306732..

[3] Turro, Nicholas J.; Leermakers, Peter A.; Vesley, George F. (1967). "Cyclohexylidenecyclohexane". Org. Synth. 47: 34. doi:10.15227/orgsyn.047.0034.

[4] Cope, Arthur C.; Ciganek, Engelbert (1959). "N,N-Dimethylcyclohexylmethylamine". Organic Syntheses. 39: 19. doi:10.15227/orgsyn.039.0019.

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