13256-11-6

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

Downstream Products

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

Relevant academic research and scientific papers

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.

Ionic liquid 1-(4-nitritobutyl)-3-methylimidazolium chloride as a new reagent for the efficient N-nitrosation of secondary amines under mild conditions

1-(4-Nitritobutyl)-3-methylimidazolium chloride has been developed as a new reagent for efficient nitrosation of secondary amines at 0 °C to room temperature. A variety of N-nitrosamines were prepared in excellent yields by use of this task-specific ionic liquid under mild and heterogeneous 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.

Synthesis, in vitro activity, and three-dimensional quantitative Structure-activity relationship of novel hydrazine inhibitors of human vascular adhesion protein-1

Vascular adhesion protein-1 (VAP-1) belongs to the semicarbazide-sensitive amine oxidases (SSAOs) that convert amines into aldehydes. SSAOs are distinct from the mammalian monoamine oxidases (MAOs), but their substrate specificities are partly overlapping. VAP-1 has been proposed as a target for anti-inflammatory drug therapy because of its role in leukocyte adhesion to endothelium. Here, we describe the synthesis and in vitro activities of novel series of VAP-1 selective inhibitors. In addition, the molecular dynamics simulations performed for VAP-1 reveal that the movements of Met211, Ser496, and especially Leu469 can enlarge the ligand-binding pocket, allowing larger ligands than those seen in the crystal structures to bind. Combining the data from molecular dynamics simulations, docking, and in vitro measurements, the three-dimensional quantitative Structure-activity relationship (3D QSAR) models for VAP-1 (q2LOO: 0.636; r2: 0.828) and MAOs (q2LOO: 0.749, r2: 0.840) were built and employed in the development of selective VAP-1 inhibitors.

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.

Effect of oxygen on the reaction of secondary amines with nitric oxide

Secondary amines were allowed to react with nitric oxide in the presence of oxygen to afford N-nitrosamines in good yields. Detailed investigation revealed that the reaction proceeded by two pathways; the one involves the catalytic behavior of oxygen, and the other consumes a stoichiometrical amount of oxygen. Both pathways afforded the same nitroso adducts.

β-KETONITROSAMINES. SYNTHETIC EQUIVALENTS OF α-METHYLENE ALKYLAMINO ANIONS (-CH2NHR).

β-Ketonitrosamines are important in the study of nitrosamine metabolism, carcinogenesis and in vivo alkylation.The enhanced acidity of protons at the α-carbon, as well as the ease of fragmentation of the title compounds establishes them as synthetic equivalents of α-methylene alkylamino anions (-CH2NHR).Anion formation is carried out with powdered sodium hydroxide - sodium carbonate in DMF or THF at 25 deg C.Reaction with an alkyl halide gives a good yield of the alkylated product.Retro-Claisen cleavage in aqueous basic media gives the corresponding dialkyl - nitrosamine or, with D2O, the deuterated analog.

Nitrosamines from Tertiary Amines and Dinitrogen Tetraoxide

A preparative nitrosolysis of aliphatic acyclic and cyclic tertiary monoamines to nitrosoamines was brought about by treatment with dinitrogen tetraoxide in carbon tetrachloride at 0-40 deg C.Dealkylation was restricted, where applicable, to demethylation.Competitive oxidation to an amide was observed in the formation of dibutylformamide from tributylamine.Diamine dinitrate salts, without nitrosamine formation, were obtained from 1,4-dimethylpiperazine and 1,4-diazabicyclo-octane; however, each dinitrate salt thermolysed at 180-200 deg C to give a small amount of 1,4-dinitrosopiperazine.In acetic anhydride dinitrogen tetraoxide converted amines less efficiently, gave lower yield of nitrosoamines, was less selective in dealkylation, and introduced the formation of by-products.

N-Nitrosoenamines, Versatile New Synthesis Intermediates

N-Nitrosoenamines are reactive toward nucleophilic reagents such as dialkylcopper lithium and enolate ions, as well as being active in electrophilic reactions such as acid-catalyzed additions.