Nitrocyclohexane

Chemical compound From Wikipedia, the free encyclopedia

Nitrocyclohexane is an organic compound with the molecular formula C6H11NO2. It is a colorless liquid, but degraded samples appear pale yellow. It once was produced commercially as a precursor to caprolactam.[1]

Quick facts Names, Identifiers ...
Nitrocyclohexane
Names
IUPAC name
Nitrocyclohexane
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.013.050 Edit this at Wikidata
UNII
  • InChI=1S/C6H11NO2/c8-7(9)6-4-2-1-3-5-6/h6H,1-5H2
    Key: NJNQUTDUIPVROZ-UHFFFAOYSA-N
  • InChI=1/C6H11NO2/c8-7(9)6-4-2-1-3-5-6/h6H,1-5H2
    Key: NJNQUTDUIPVROZ-UHFFFAOYAA
  • [O-][N+](=O)C1CCCCC1
Properties
C6H11NO2
Molar mass 129.159 g·mol−1
Density 1.061 g/cm3
Melting point −34 °C (−29 °F; 239 K)
Boiling point 205.8 °C (402.4 °F; 478.9 K)
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

It is prepared by reaction of nitrogen dioxide with cyclohexane, the so-called Nixian process.[1] Cyclohexane is a convenient substrate because all twelve C-H bonds are equivalent, so mononitration does not give isomers (unlike the case of n-hexane).[2]

Hazards

Nitrocyclohexane is highly flammable and a strong oxidizing agent.[3] It is listed as an extremely hazardous substance by the Emergency Planning and Community Right-to-Know Act, and the NOAA warns that it can be explosive.[3]

References

Further reading

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