36239-05-1

Basic information

• Product Name: N-Methyl-N-nitrobenzylamine
• Synonyms: N-Methyl-N-nitrobenzylamine
• CAS NO: 36239-05-1
• Molecular Weight: 166.18
• Mol File: 36239-05-1.mol

Chemical Properties

• CAS DataBase Reference: N-Methyl-N-nitrobenzylamine(CAS DataBase Reference)
• NIST Chemistry Reference: N-Methyl-N-nitrobenzylamine(36239-05-1)
• EPA Substance Registry System: N-Methyl-N-nitrobenzylamine(36239-05-1)

Safety Data

• Hazardous Substances Data: 36239-05-1(Hazardous Substances Data)

Upstream product

• 36239-01-7 1-acetoxy-2-nitro-2-azapropane 
• 71-43-2 benzene 
• 103-67-3 benzyl-methyl-amine 
• 102-05-6 N-methyldibenzylamine 
• 103-83-3 N,N'-dimethylbenzylamine 
• 937-40-6 Benzylmethylnitrosamin 
• 64284-25-9 sodium salt of methylnitramine 
• 100-44-7 benzyl chloride 
• 598-57-2 methylnitroamine 
• 100-39-0 benzyl bromide 

Downstream Products

• 622-29-7 N-Benzylidenemethylamine 
• 582-25-2 Potassium benzoate 
• 100-52-7 benzaldehyde 
• 74-89-5 methylamine 

Relevant articles and documents

Formation of N-nitrosamines and N-nitramines by the reaction of secondary amines peroxynitrite and other reactive nitrogen species: Comparison with nitrotyrosine formation

Reactive nitrogen species, including nitrogen oxides (N2O3 and N2O4), peroxynitrite (ONOO-), and nitryl chloride (NO2Cl), have been implicated as causes of inflammation and cancer. We studied reactions of secondary amines with peroxynitrite and found that both N-nitrosamines and N- nitramines were formed. Morpholine was more easily nitrosated by peroxynitrite at alkaline pH than at neutral pH, whereas its nitration by peroxynitrite was optimal at pH 8.5. The yield of nitrosomorpholine in this reaction was 3 times higher than that of nitromorpholine at alkaline pH, whereas 2 times more nitromorpholine than nitrosomorpholine was formed at pH 2N·), which react with nitric oxide (·NO) or nitrogen dioxide (·NO2) to yield nitroso and nitro secondary amines, respectively. Reaction of morpholine with NO· and superoxide anion (O2·-), which were concomitantly produced from spermine NONOate and by the xanthine oxidase systems, respectively, also yielded nitromorpholine, but its yield was 2·- inhibited its formation. Reactions of morpholine with nitrite plus HOCl or nitrite plus H2O2, with or without addition of myeloperoxidase or horseradish peroxidase, also yielded nitration and nitrosation products, in yields that depended on the reactants. Tyrosine was nitrated easily by synthetic peroxynitrite, by NaNO2 plus H2O2 with myeloperoxidase, and by NaNO2 plus H2O2 under acidic conditions. Nitrated secondary amines, e.g., N-nitroproline, could be identified as specific markers for endogenous nitration mediated by reactive nitrogen species.

N-Nitration of Secondary Amines with 4-Chloro-5-methoxy-2-nitropyridazin-3-one

N-Nitration of 4-chloro-5-substituted-pyridazin-3-one with copper nitrate trihydrate in acetic anhydride gave the corresponding 4-chloro-2-nitro-5-substituted-pyridazin-3-one. 4-Chloro-5-alkoxy-2-nitropyridazin-3-ones such as 5-methoxy (2b) and 5-ethoxy (2d) derivatives showed excellent nitro group transfer potentiality. N-Nitration of some secondary amines with 2b gave the corresponding N-nitramines under mild neutral condition in good yields.