937-40-6

Basic information

• Product Name: BENZYL METHYL NITROSAMINE
• Synonyms: BENZYL METHYL NITROSAMINE;N-METHYL-N-BENZYLNITROSAMINE;Benzenemethanamine,N-methyl-N-nitroso-;Benzylamine,N-methyl-N-nitroso-;Methyl(benzyl)nitrosamine;methylbenzylnitrosamine;methyl-benzyl-nitrosoamin;nitrosobenzylmethylamine
• CAS NO: 937-40-6
• Molecular Formula: C₈H₁₀N₂O
• Molecular Weight: 150.18
• Mol File: 937-40-6.mol
• Article Data: 12

Chemical Properties

• Boiling Point: 271.72°C (rough estimate)
• Flash Point: 134.1°C
• Appearance: /
• Density: 1.1392 (rough estimate)
• Vapor Pressure: 0.00229mmHg at 25°C
• Refractive Index: 1.6180 (estimate)
• Storage Temp.: Refrigerator, Under inert atmosphere
• Solubility: Chloroform (Sparingly), Methanol (Slightly)
• PKA: -4.77±0.70(Predicted)
• Water Solubility: 4.505g/L(24 oC)
• CAS DataBase Reference: BENZYL METHYL NITROSAMINE(CAS DataBase Reference)
• NIST Chemistry Reference: BENZYL METHYL NITROSAMINE(937-40-6)
• EPA Substance Registry System: BENZYL METHYL NITROSAMINE(937-40-6)

Safety Data

• Hazardous Substances Data: 937-40-6(Hazardous Substances Data)

Usage

Uses

N-Nitroso-N-methylbenzylamine induced neoplasia in mice. Mice treated intragastrically with N-Nitroso-N-methylbenzylamine developed multiple tumours. Mice carrying one inactivated Fhit allele (Fhit +?/- mice) are highly susceptible to tumor induction by N-?nitrosomethylbenzylamine.

Safety Profile

Poison by ingestion. Questionable carcinogen with experimental tumorigenic data. Mutation data reported. When heated to decomposition it emits toxic fumes of NOx. See also NITROSAMINES.

InChI:InChI=1/C8H10N2O/c1-10(9-11)7-8-5-3-2-4-6-8/h2-6H,7H2,1H3

Upstream product

• 91245-57-7 N-benzyl-N-cyclopropyl-N-methylamine 
• 102-05-6 N-methyldibenzylamine 
• 64-19-7 acetic acid 
• 100-52-7 benzaldehyde 
• 13324-66-8 N-benzylcyclopropanamine 
• 10311-10-1 1-bromo-2-nitrosooxy-ethane 
• 103-67-3 benzyl-methyl-amine 
• 87014-46-8 C₇H₇N₂O^(1-)*K⁽¹⁺⁾ 
• 74-88-4 methyl iodide 
• 80-11-5 N-methyl-N-nitrosotoluene-p-sulfonamide 
• 41051-51-8 2-ethoxyethyl nitrite 
• 87039-32-5 potassium methyl(nitroso)amide 
• 620-05-3 iodomethylbenzene 
• 132931-83-0 3-Benzyl-3-methyl-1-(4-tolyl)-1-nitrosourea 

Downstream Products

• 97216-15-4 2-Hydroxy-thiobenzoesaeure-(N²-methyl-N²-benzyl-hydrazid) 
• 100-52-7 benzaldehyde 
• 65-85-0 benzoic acid 
• 100-51-6 benzyl alcohol 
• 622-29-7 N-Benzylidenemethylamine 
• 92852-70-5 2-Hydroxy-5-nitro-benzal-methylbenzylhydrazin 
• 103-67-3 benzyl-methyl-amine 
• 36239-05-1 N-Methyl-N-nitrobenzylamine 
• 29804-93-1 N'-benzyl-N'-methylformohydrazide 
• 3931-52-0 1-benzyl-1-methylhydrazine 

Relevant articles and documents

Nitromethane with IBX/TBAF as a nitrosating agent: Synthesis of nitrosamines from secondary or tertiary amines under mild conditions

Aliphatic or aromatic N,N-disubstituted nitrosamine was generated in fair to excellent yield from the reaction of a secondary or tertiary amine with o-iodoxybenzoic acid (IBX) or o-iodosylbenzoic acid (IBA)/R4NX (X = halide) and nitromethane. The product yield was strongly influenced by both the halide of R4NX and iodanes. IBX gave a higher yield than IBA, while the halides follow F- > Cl- > Br- ～ I-. Nitrous acid formed in situ from nitromethane and IBX (or IBA)/halides is likely responsible for the observed reaction.

N-Alkyl-N-Cyclopropylanilines as Mechanistic Probes in the Nitrosation of N,N-Dialkyl Aromatic Amines

A group of N-cyclopropyl-N-alkylanilines has been synthesized, and their reaction with nitrous acid in aqueous acetic acid at 0°C was examined. All compounds reacted rapidly to produce the corresponding N-alkyl-N-nitrosoaniline by specific cleavage of the cyclopropyl group from the nitrogen. The transformations were unaffected by the nature of the alkyl substituent (Me, Et, iPr, Bn). The reaction of 4-chloro-N-2-phenylcyclopropyl-N-methylaniline with nitrous acid gave 4-chloro-N-methyl-N-nitrosoaniline (76%), cinnamaldehyde (55%), 3-phenyl-5-hydroxyisoxazoline (26%), and 5-(N-4-chlorophenylmethylamino)-3-phenylisoxazoline (8%). Both the selective cleavage of the cyclopropyl group from the aromatic amine nitrogen and nature of the products derived from the cyclopropane ring support a mechanism involving the formation of an amine radical cation. This step is followed by rapid cyclopropyl ring opening to produce an iminium ion with a C-centered radical which either combines with NO or is oxidized.

Pseudophase Approach to Reactivity in Microemulsions: Quantitative Explanation of the Kinetics of the Nitrosation of Amines by Alkyl Nitrides in AOT/Isooctane/Water Microemulsions

The kinetics of the nitroso group transfer from 2-ethoxyethyl (EEN) and 2-bromoethyl (BEN) nitrit+e to the secondary amines piperazine (PIP), N-methylbenzylamine (NMBA), and morpholine (MOR) in bis(2-ethylhexyl) sulfosuccinate (AOT)/isooctane(iC8)/water microemulsions were determined.They are explained quantitatively in terms of a model in which the reagents are distributed among the aqueous, organic, and AOT film surfactant, with the aqueous pseudophase and the surfactant film as the losi of the reaction.