Cyclohexane

Cyclohexane
Cyclohexane	3D structure of a cyclohexane molecule
Skeletal formula of cyclohexane in its chair conformation	Ball-and-stick model of cyclohexane in its chair conformation
Names
	Preferred IUPAC name Cyclohexane
	Other names Hexanaphthene (archaic)
Identifiers
CAS Number	110-82-7 ;
3D model (JSmol)	Interactive image;
3DMet	B04304;
Beilstein Reference	1900225
ChEBI	CHEBI:29005 ;
ChEMBL	ChEMBL15980 ;
ChemSpider	7787 ;
DrugBank	DB03561 ;
ECHA InfoCard	100.003.461
Gmelin Reference	1662
KEGG	C11249 ;
PubChem CID	8078;
RTECS number	GU6300000;
UNII	48K5MKG32S ;
UN number	1145
CompTox Dashboard (EPA)	DTXSID4021923 ;
	InChI InChI=1S/C6H12/c1-2-4-6-5-3-1/h1-6H2 Key: XDTMQSROBMDMFD-UHFFFAOYSA-N ; InChI=1/C6H12/c1-2-4-6-5-3-1/h1-6H2 Key: XDTMQSROBMDMFD-UHFFFAOYAZ;
	SMILES C1CCCCC1;
Properties
Chemical formula	C6H12
Molar mass	84.162 g·mol−1
Appearance	Colourless liquid
Odor	Sweet, gasoline-like
Density	0.7739 g/ml (liquid); 0.996 g/ml (solid)
Melting point	6.47 °C (43.65 °F; 279.62 K)
Boiling point	80.74 °C (177.33 °F; 353.89 K)
Solubility in water	Immiscible
Solubility	Soluble in ether, alcohol, acetone
Vapor pressure	78 mmHg (20 °C)
Magnetic susceptibility (χ)	−68.13·10−6 cm3/mol
Refractive index (nD)	1.42662
Viscosity	1.02 cP at 17 °C
Hazards
	GHS labelling:
Pictograms
Signal word	Danger
Hazard statements	H225, H304, H315, H336
Precautionary statements	P210, P233, P240, P241, P242, P243, P261, P264, P271, P273, P280, P301+P310, P302+P352, P303+P361+P353, P304+P340, P312, P321, P331, P332+P313, P362, P370+P378, P391, P403+P233, P403+P235, P405, P501
NFPA 704 (fire diamond)	1 3 0
Flash point	−20 °C (−4 °F; 253 K)
Autoignition; temperature	245 °C (473 °F; 518 K)
Explosive limits	1.3–8%
	Lethal dose or concentration (LD, LC):
LD50 (median dose)	12705 mg/kg (rat, oral); 813 mg/kg (mouse, oral)
LCLo (lowest published)	17,142 ppm (mouse, 2 h); 26,600 ppm (rabbit, 1 h)
	NIOSH (US health exposure limits):
PEL (Permissible)	TWA 300 ppm (1050 mg/m3)
REL (Recommended)	TWA 300 ppm (1050 mg/m3)
IDLH (Immediate danger)	1300 ppm
Thermochemistry
Std enthalpy of; formation (ΔfH⦵298)	−156 kJ/mol
Std enthalpy of; combustion (ΔcH⦵298)	−3920 kJ/mol
Related compounds
Related cycloalkanes	Cyclopentane; Cycloheptane
Related compounds	Cyclohexene; Benzene
Supplementary data page
	Cyclohexane (data page)
	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

Cyclohexane is a cycloalkane with the molecular formula C₆H₁₂. Cyclohexane is non-polar. Cyclohexane is a colourless, flammable liquid with a distinctive detergent-like odor, reminiscent of cleaning products (in which it is sometimes used). Cyclohexane is mainly used for the industrial production of adipic acid and caprolactam, which are precursors to nylon.^[5]

Cyclohexyl (C₆H₁₁) is the alkyl substituent of cyclohexane and is abbreviated Cy.^[6]

^ "Hexanaphthene". dictionary.com. Archived from the original on 2018-02-12.
^ "Front Matter". Nomenclature of Organic Chemistry : IUPAC Recommendations and Preferred Names 2013 (Blue Book). Cambridge: The Royal Society of Chemistry. 2014. pp. P001–P004. doi:10.1039/9781849733069-FP001. ISBN 978-0-85404-182-4.
^ ^a ^b ^c ^d ^e NIOSH Pocket Guide to Chemical Hazards. "#0163". National Institute for Occupational Safety and Health (NIOSH).
^ ^a ^b "Cyclohexane". Immediately Dangerous to Life or Health Concentrations (IDLH). National Institute for Occupational Safety and Health (NIOSH).
^ Campbell, M. Larry (2011). "Cyclohexane". Ullmann's Encyclopedia of Industrial Chemistry. doi:10.1002/14356007.a08_209.pub2. ISBN 978-3527306732.
^ "Standard Abbreviations and Acronyms" (PDF). The Journal of Organic Chemistry.

[1] "Hexanaphthene". dictionary.com. Archived from the original on 2018-02-12.

[iupac2013-2] "Front Matter". Nomenclature of Organic Chemistry : IUPAC Recommendations and Preferred Names 2013 (Blue Book). Cambridge: The Royal Society of Chemistry. 2014. pp. P001–P004. doi:10.1039/9781849733069-FP001. ISBN 978-0-85404-182-4.

[PGCH-3] NIOSH Pocket Guide to Chemical Hazards. "#0163". National Institute for Occupational Safety and Health (NIOSH).

[IDLH-4] "Cyclohexane". Immediately Dangerous to Life or Health Concentrations (IDLH). National Institute for Occupational Safety and Health (NIOSH).

[Campbell2011-5] Campbell, M. Larry (2011). "Cyclohexane". Ullmann's Encyclopedia of Industrial Chemistry. doi:10.1002/14356007.a08_209.pub2. ISBN 978-3527306732.

[6] "Standard Abbreviations and Acronyms" (PDF). The Journal of Organic Chemistry.

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