Nitrocyclohexane

Nitrocyclohexane

Names
IUPAC name Nitrocyclohexane
Identifiers
CAS Number	1122-60-7  Y
3D model (JSmol)	Interactive image
ChemSpider	13647
ECHA InfoCard	100.013.050
PubChem CID	14285
UNII	LL1X024M73  Y
CompTox Dashboard (EPA)	DTXSID6061529
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. ^[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. 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. "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.