NITROCYCLOHEXANE

Synthesis Reference(s)

Journal of the American Chemical Society, 75, p. 4047, 1953 DOI: 10.1021/ja01112a049Tetrahedron, 46, p. 7443, 1990 DOI: 10.1016/S0040-4020(01)89059-1Tetrahedron Letters, 21, p. 1117, 1980 DOI: 10.1016/S0040-4039(01)83928-9

Air & Water Reactions

Highly Flammable

Reactivity Profile

Nitroalkanes, such as NITROCYCLOHEXANE, range from slight to strong oxidizing agents. If mixed with reducing agents, including hydrides, sulfides and nitrides, they may begin a vigorous reaction that culminates in a detonation. Nitroalkanes are milder oxidizing agents, but still react violently with reducing agents at higher temperature and pressures. Nitroalkanes react with inorganic bases to form explosive salts. The presence of metal oxides increases the thermal sensitivity of nitroalkanes. Nitroalkanes with more than one nitro group are generally explosive. Nitroalkanes are insoluble in water. Flammable/combustible material. May be ignited by heat, sparks or flames.

Potential Exposure

Used in organic synthesis.

Shipping

UN3382 Toxic by inhalation liquid, n.o.s. with an LC50 lower than or equal to 1000 ml/m3 and saturated vapor concentration ≥10 LC50, Hazard Class: 6.1; Labels: 6.1 Technical Name Required, Inhalation Hazard Zone B.

Incompatibilities

A nitro compound; a fire and explosive hazard. May form explosive mixture with air. Nitrocyclohexane, a nitroalkane, is a strong oxidizing agents. If mixed with reducing agents, including hydrides, sulfides and nitrides, they may begin a vigorous reaction that culminates in a detonation. Nitroalkanes are milder oxidizing agents, but still react violently with reducing agents at higher temperature and pressures. Nitroalkanes react with inorganic bases to form explosive salts. The presence of metal oxides increases the thermal sensitivity of nitroalkanes. Nitroalkanes with more than one nitro group are generally explosive. Incompatible with alkalis, and metal oxides. This chemical is highly reactive and may be heat-and shock-sensitive.

Waste Disposal

Dissolve or mix the material with a combustible solvent and burn in a chemical incinerator equipped with an afterburner and scrubber. All federal, state, and local environmental regulations must be observed.

General Description

Nitrocyclohexane is a nitroalkane derivative that can be synthesized through various methods, including the reduction of 1,1-dinitrocyclohexane, where it forms as a product alongside other compounds like 1,1′-dinitrobicyclohexyl. It is also produced selectively in the vapor-phase catalytic nitration-oxidation of cyclohexane with NO₂ , yielding nitrocyclohexane and adipic acid. NITROCYCLOHEXANE exhibits reactivity in electron transfer reactions, where its radical intermediates participate in chain reactions. Additionally, nitrocyclohexane can be derived from the reduction of gem-bromonitro compounds or through the oxidation of azides using HOF·CH₃ CN. These synthetic routes highlight its versatility as an intermediate in organic transformations.

Definition

ChEBI: A C-nitro compound that is cyclohexane in which a single hydrogen is replaced by a nitro group.