Nitrocyclohexane

Nitrocyclohexane

Error creating thumbnail:
Error creating thumbnail:
Names
IUPAC name Nitrocyclohexane
Identifiers
CAS Number	1122-60-7 checkY
3D model (JSmol)	Interactive image
ChemSpider	13647
ECHA InfoCard
E number
PubChem CID	14285
UNII	LL1X024M73 checkY
CompTox Dashboard (EPA)	{{#property:P3117}}
InChI 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
SMILES [O-][N+](=O)C1CCCCC1
Properties
Chemical formula	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). Infobox references

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.

Preparation

It is prepared by reaction of nitrogen dioxide with cyclohexane, the so-called Nixian process. 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).

Hazards

Nitrocyclohexane is highly flammable and a strong oxidizing agent. 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.