932-83-2

Basic information

• Product Name: N-NITROSOHEXAMETHYLENEIMINE
• Synonyms: hexahydro-1-nitroso-1h-azepin;hexahydro-1-nitroso-1h-azepine;n-6-mi;n-nitrosoazacycloheptane;n-nitrosohexahydroazepine;n-nitrosoperhydroazepine;N-NITROSOHEXAMETHYLENEIMINE;HEXAHYDRO-1-NITROSOAZEPINE
• CAS NO: 932-83-2
• Molecular Formula: C₆H₁₂N₂O
• Molecular Weight: 128.17
• EINECS: 213-258-6
• Mol File: 932-83-2.mol
• Article Data: 8

Chemical Properties

• Boiling Point: 233 °C(lit.)
• Flash Point: 99 °C
• Appearance: /
• Density: 1.06 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.0414mmHg at 25°C
• Refractive Index: n20/D 1.497(lit.)
• Storage Temp.: 2-8°C
• Solubility: Chloroform (Slightly), Methanol (Slightly)
• PKA: -3.18±0.20(Predicted)
• Water Solubility: 12.82g/L(24 oC)
• CAS DataBase Reference: N-NITROSOHEXAMETHYLENEIMINE(CAS DataBase Reference)
• NIST Chemistry Reference: N-NITROSOHEXAMETHYLENEIMINE(932-83-2)
• EPA Substance Registry System: N-NITROSOHEXAMETHYLENEIMINE(932-83-2)

Safety Data

• Hazard Codes: T
• Statements: 45-22-36/37/38
• Safety Statements: 53-36/37/39-45
• WGK Germany: 3
• RTECS: CM3325000
• Hazardous Substances Data: 932-83-2(Hazardous Substances Data)

Usage

Uses

N-Nitrosohexamethylenimine is a carcinogen.

Safety Profile

Poison by ingestion. Experimental teratogenic and reproductive effects. Questionable carcinogen with experimental neoplastigenic data. Mutation data reported. Many N-nitroso compounds are carcinogens. When heated to decomposition it emits very toxic fumes of NO, and SOx. See also N-NITROSO COMPOUNDS.

InChI:InChI=1/C6H12N2O/c9-7-8-5-3-1-2-4-6-8/h1-6H2

Upstream product

• 111-49-9 hexamethylene imine 
• 544-16-1 n-Butyl nitrite 
• 543-67-9 n-propyl nitrite 

Relevant articles and documents

The Use of Potassium/Sodium Nitrite as a Nitrosating Agent in the Electrooxidative N-Nitrosation of Secondary Amines

We report herein on the electrochemical N-nitrosation of secondary amines using widely available sodium/potassium nitrite as a nitrosating agent. This approach not only eliminates the need for using a combination of sodium/potassium and a strong acid but also has good functional group tolerance. The reaction is compatible with the late-stage modification of pharmaceutical compounds and could be conducted in gram scale with a high reaction efficiency. Preliminary mechanistic studies indicate that the N-nitrosation occurs via the anodic oxidation of KNO2 into an NO2 radical which is then transformed into an NO+ cation.

Efficient procedure for chemoselective N-nitrosation of secondary amines with trichloromelamine-NaNO2

A combination of trichloromelamine and sodium nitrite in the presence of wet silica gel was used as an effective nitrosating agent for the transformation of secondary amines into the corresponding N-nitroso derivatives under mild and heterogeneous conditions in good to excellent yields.

Alumina-methanesulfonic acid (AMA)/NaNO2 as an efficient procedure for the chemoselectivite N-nitrosation of secondary amines

A combination of alumina/methanesulfonic acid (AMA) and sodium nitrite was used as an effective nitrosating agent for the nitrosation of secondary amines under mild and heterogeneous conditions in good to excellent yields. Copyright Taylor & Francis Group, LLC.