// Workers AI · dad joke modeWhat did nitrocyclohexane say? "I'm explosive with excitement
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| Names | |
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| IUPAC name
Nitrocyclohexane | |
| Identifiers | |
3D model (JSmol) |
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| Abbreviations | CyNO2 |
| ChemSpider | |
| ECHA InfoCard | 100.013.050 |
PubChem CID |
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| UNII | |
CompTox Dashboard (EPA) |
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| 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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Nitrocyclohexane is an organic compound with the molecular formula C6H11NO2 or (CH2)5CHNO2. It is a colorless liquid, but degraded samples appear pale yellow. It once was produced commercially as a precursor to caprolactam.[1]
Preparation
[edit]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
[edit]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
[edit]- 1 2 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.
- ↑ 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.
- 1 2 "Cameo Chemicals - NITROCYCLOHEXANE". Retrieved July 9, 2012.
Further reading
[edit]- 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.