16338-97-9

Basic information

• Product Name: diallylnitrosamine
• Synonyms: diallylnitrosamine;N-NITROSODIALLYLAMINE
• CAS NO: 16338-97-9
• Molecular Formula: C₆H₁₀N₂O
• Molecular Weight: 126.18
• Mol File: 16338-97-9.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 234.28°C (rough estimate)
• Flash Point: 83.4°C
• Appearance: /
• Density: 1.1192 (rough estimate)
• Vapor Pressure: 0.23mmHg at 25°C
• Refractive Index: 1.5010 (estimate)
• CAS DataBase Reference: diallylnitrosamine(CAS DataBase Reference)
• NIST Chemistry Reference: diallylnitrosamine(16338-97-9)
• EPA Substance Registry System: diallylnitrosamine(16338-97-9)

Safety Data

• Hazardous Substances Data: 16338-97-9(Hazardous Substances Data)

Usage

Safety Profile

Moderately toxic by ingestion andsubcutaneous routes. Questionable carcinogen withexperimental carcinogenic, neoplastigenic, andtumorigenic data. Mutation data reported. When heated todecomposition it emits toxic fumes of NOx.

InChI:InChI=1/C6H10N2O/c1-3-5-8(7-9)6-4-2/h3-4H,1-2,5-6H2

Upstream product

• 95448-17-2 C₆H₁₀ClNO₂S 
• 124-02-7 diallylamine 

Downstream Products

• 5164-11-4 N,N-diallyl-hydrazine 
• 91959-83-0 5-Nitro-2-hydroxy-benzal-diallylhydrazin 

Relevant articles and documents

Substrate promiscuity of ortho-naphthoquinone catalyst: Catalytic aerobic amine oxidation protocols to deaminative cross-coupling and n-nitrosation

ortho-Naphthoquinone-based organocatalysts have been identified as versatile aerobic oxidation catalysts. Primary amines were readily cross-coupled with primary nitroalkanes via deaminative pathway to give nitroalkene derivatives in good to excellent yields. Secondary and tertiary amines were inert to ortho-naphthoquinone catalysts; however, secondary nitroalkanes were readily converted by ortho-naphthoquinone catalysts to the corresponding nitrite species that in situ oxidized the amines to the corresponding N-nitroso compounds. Without using harsh oxidants in a stoichiometric amount, the present catalytic aerobic oxidation protocol utilizes the substrate promiscuity feature to provide a facile access to amine oxidation products under mild reaction conditions.

Copper(II)-catalyzed oxidative N-nitrosation of secondary and tertiary amines with nitromethane under an oxygen atmosphere

The combination of a catalytic amount of Cu(OTf)2 and less than a stoichiometric amount of 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) under an O2 atmosphere effectively promoted the N-nitrosation of both secondary aromatic/aliphatic amines and tertiary aromatic amines with nitromethane (CH3NO2) leading to the preparation of N-nitrosamine derivatives.

N-NITROSAMINES FROM THE REACTION OF SULFAMOYLCHLORIDES WITH SODIUM NITRITE

N,N-Dialkylsulfamoyl chlorides react smoothly with sodiun nitrite in acetonitrile to afford the corresponding N-nitrosamines in nearly quantitative yields.