Nitrocyclohexane

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title: "Nitrocyclohexane" type: doc version: 1 created: 2026-02-28 author: "Wikipedia contributors" status: active scope: public tags: ["poisons", "nitroalkanes", "cyclohexyl-compounds", "convulsants"] topic_path: "general/poisons" source: "https://en.wikipedia.org/wiki/Nitrocyclohexane" license: "CC BY-SA 4.0" wikipedia_page_id: 0 wikipedia_revision_id: 0

| Name = | ImageFile = Nitrocyclohexane.svg | ImageFile1 = Nitrocyclohexane molecule spacefill.png | ImageSize = 200px | IUPACName = Nitrocyclohexane | OtherNames = | SystematicName = | Section1 = {{Chembox Identifiers | CASNo = 1122-60-7 | CASNo_Ref = | UNII_Ref = | UNII = LL1X024M73 | PubChem = 14285 | ChemSpiderID = 13647 | SMILES = [O-]N+C1CCCCC1 | InChI = 1/C6H11NO2/c8-7(9)6-4-2-1-3-5-6/h6H,1-5H2 | InChIKey = NJNQUTDUIPVROZ-UHFFFAOYAA | StdInChI = 1S/C6H11NO2/c8-7(9)6-4-2-1-3-5-6/h6H,1-5H2 | StdInChIKey = NJNQUTDUIPVROZ-UHFFFAOYSA-N | Section2 = {{Chembox Properties | C=6 | H=11 | N=1 | O=2 | Appearance = | Density = 1.061 g/cm3 | MeltingPtC = -34 | BoilingPtC = 205.8 | Solubility = | Section3 = {{Chembox Hazards | MainHazards = | FlashPt = | AutoignitionPt = | Section4 = | Section5 = | Section6 =

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.

References

References

  1. (2015). "Ullmann's Encyclopedia of Industrial Chemistry".
  2. (2001). "Efficient Catalytic Alkane Nitration with NO2 under Air Assisted by N-Hydroxyphthalimide". Angewandte Chemie International Edition.
  3. "Cameo Chemicals - NITROCYCLOHEXANE".

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poisonsnitroalkanescyclohexyl-compoundsconvulsants