13256-11-6

Basic information

• Product Name: nitrosomethyl-(2-phenylethyl)amine
• Synonyms: nitrosomethyl-(2-phenylethyl)amine
• CAS NO: 13256-11-6
• Molecular Formula: C₉H₁₂N₂O
• Molecular Weight: 164.23
• Mol File: 13256-11-6.mol
• Article Data: 10

Chemical Properties

• Boiling Point: 291.67°C (rough estimate)
• Flash Point: 143.3°C
• Appearance: /
• Density: 1.1062 (rough estimate)
• Vapor Pressure: 0.00092mmHg at 25°C
• Refractive Index: 1.5373 (estimate)
• CAS DataBase Reference: nitrosomethyl-(2-phenylethyl)amine(CAS DataBase Reference)
• NIST Chemistry Reference: nitrosomethyl-(2-phenylethyl)amine(13256-11-6)
• EPA Substance Registry System: nitrosomethyl-(2-phenylethyl)amine(13256-11-6)

Safety Data

• Hazardous Substances Data: 13256-11-6(Hazardous Substances Data)

Usage

Safety Profile

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

InChI:InChI=1/C9H12N2O/c1-11(10-12)8-7-9-5-3-2-4-6-9/h2-6H,7-8H2,1H3

Upstream product

• 62-75-9 N-Nitrosodimethylamine 
• 100-39-0 benzyl bromide 
• 4549-40-0 methylvinylnitrosamine 
• 591-51-5 phenyllithium 
• 1126-71-2 N,N-dimethylphenethylamine 
• 589-08-2 N-Methyl-N-phenethylamine 
• 100-46-9 benzylamine 

Downstream Products

• 100221-57-6 N-Methyl-N-nitro-β-phenethylamine 
• 589-08-2 N-Methyl-N-phenethylamine 
• 154493-27-3 1-methyl-1-(2-phenylethyl)hydrazine hydrochloride 

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.

1-butyl-3-methylimidazolium nitrite as a reagent for the efficient n-nitrosation of secondary amines

1-Butyl-3-methylimidazolium nitrite, [bmim]NO2 was used as a new effective reagent for the preparation of N-nitrosamines from the corresponding secondary amines at 0 °C to room temperature, under mild conditions in good to excellent yields.

Reaction of secondary and tertiary amines with nitric oxide in the presence of oxygen

In order to clarify the role of oxygen in the reaction of amines with nitric oxide, secondary amines were allowed to react with nitric oxide in the presence of oxygen. Although N-nitrosamines were obtained as the main products in every case, the yields depended on the substituents and reaction solvents. Detailed investigation revealed that the reaction proceeded by at least two pathways: one involving oxygen as a catalyst, and the other consuming the stoichiometric amount of oxygen. Both paths afforded the same nitroso adducts. It was suggested that a third path, a catalytic process via Drago's salts was also possible. The same reaction was applied to a tertiary amine, and it was found that the oxygen was consumed stoichiometrically in this case.