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Cyclohexane information


Cyclohexane
Cyclohexane
Cyclohexane
3D structure of a cyclohexane molecule
3D structure of a cyclohexane molecule
Skeletal formula of cyclohexane in its chair conformation
Skeletal formula of cyclohexane in its chair conformation
Ball-and-stick model of cyclohexane in its chair conformation
Ball-and-stick model of cyclohexane in its chair conformation
Names
Preferred IUPAC name
Cyclohexane[2]
Other names
Hexanaphthene (archaic)[1]
Identifiers
CAS Number
  • 110-82-7 checkY
3D model (JSmol)
  • Interactive image
3DMet
  • B04304
Beilstein Reference
1900225
ChEBI
  • CHEBI:29005 checkY
ChEMBL
  • ChEMBL15980 checkY
ChemSpider
  • 7787 checkY
DrugBank
  • DB03561 checkY
ECHA InfoCard 100.003.461 Edit this at Wikidata
Gmelin Reference
1662
KEGG
  • C11249 checkY
PubChem CID
  • 8078
RTECS number
  • GU6300000
UNII
  • 48K5MKG32S checkY
UN number 1145
CompTox Dashboard (EPA)
  • DTXSID4021923 Edit this at Wikidata
InChI
  • InChI=1S/C6H12/c1-2-4-6-5-3-1/h1-6H2 checkY
    Key: XDTMQSROBMDMFD-UHFFFAOYSA-N checkY
  • 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)[3]
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
GHS02: Flammable GHS08: Health hazard GHS07: Exclamation mark GHS09: Environmental hazard
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)
NFPA 704 four-colored diamondHealth 1: Exposure would cause irritation but only minor residual injury. E.g. turpentineFlammability 3: Liquids and solids that can be ignited under almost all ambient temperature conditions. Flash point between 23 and 38 °C (73 and 100 °F). E.g. gasolineInstability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no code
1
3
0
Flash point −20 °C (−4 °F; 253 K)
Autoignition
temperature
245 °C (473 °F; 518 K)
Explosive limits 1.3–8%[3]
Lethal dose or concentration (LD, LC):
LD50 (median dose)
12705 mg/kg (rat, oral)
813 mg/kg (mouse, oral)[4]
LCLo (lowest published)
17,142 ppm (mouse, 2 h)
26,600 ppm (rabbit, 1 h)[4]
NIOSH (US health exposure limits):
PEL (Permissible)
TWA 300 ppm (1050 mg/m3)[3]
REL (Recommended)
TWA 300 ppm (1050 mg/m3)[3]
IDLH (Immediate danger)
1300 ppm[3]
Thermochemistry
Std enthalpy of
formation fH298)
−156 kJ/mol
Std enthalpy of
combustion cH298)
−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).
checkY verify (what is checkY☒N ?)
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]

  1. ^ "Hexanaphthene". dictionary.com. Archived from the original on 2018-02-12.
  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.
  3. ^ a b c d e NIOSH Pocket Guide to Chemical Hazards. "#0163". National Institute for Occupational Safety and Health (NIOSH).
  4. ^ a b "Cyclohexane". Immediately Dangerous to Life or Health Concentrations (IDLH). National Institute for Occupational Safety and Health (NIOSH).
  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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conformation, unlike the preference for a chair form of cyclohexane. One basis for the cyclohexane conformational preference for a chair is that it allows...

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Anomeric effect

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