Nitrocyclohexane

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).

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]

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

  1. ^ a b Teles, J. Henrique; Hermans, Ive; Franz, Gerhard; Sheldon, Roger A. (2015). "Oxidation". Ullmann's Encyclopedia of Industrial Chemistry. pp. 1–103. doi:10.1002/14356007.a18_261.pub2. ISBN 978-3-527-30385-4.
  2. ^ Sakaguchi, Satoshi; Nishiwaki, Yoshiki; Kitamura, Takaaki; Ishii, Yasutaka (2001). "Efficient Catalytic Alkane Nitration with NO2 under Air Assisted by N-Hydroxyphthalimide". Angewandte Chemie International Edition. 40: 222–224. doi:10.1002/1521-3773(20010105)40:1<222::AID-ANIE222>3.0.CO;2-W.
  3. ^ a b "Cameo Chemicals - NITROCYCLOHEXANE". Retrieved July 9, 2012.

Further reading

  • Iffland, Don C.; Criner, G. X. (1953). "Preparation of Nitro Compounds from Oximes. II. The Improved Synthesis of Nitrocycloalkanes". Journal of the American Chemical Society. 75 (16): 4047. doi:10.1021/ja01112a049.
  • Fahim, Hussein; Fleifel, Abdallah; Fahim, Fawzia (1960). "Synthesis of 1-Benzylnaphthalenes". The Journal of Organic Chemistry. 25 (6): 1040–1041. doi:10.1021/jo01076a605.