89937-90-6

Upstream product

• 110-86-1 pyridine 
• 64-17-5 ethanol 
• 509-14-8 tetranitromethane 
• 610-17-3 N,N-dimethyl-2-nitro-benzenamine 
• 612-28-2 2-nitro-N-methylaniline 
• 64-19-7 acetic acid 
• 7119-93-9 N-methyl-N-nitroaniline 
• 100-61-8 N-methylaniline 
• 88-73-3 2-Chloronitrobenzene 
• 121-69-7 N,N-dimethyl-aniline 
• 110-46-3 isopentyl nitrite 
• 51661-19-9 1,2-bis(2-nitrophenoxy)ethane 

Downstream Products

• 4760-34-3 N-methyl-1,2-phenylenediamine 
• 254-87-5 1,2,4-benzotriazene 

Relevant academic research and scientific papers

Rhodium(iii)-catalyzed indole synthesis at room temperature using the transient oxidizing directing group strategy

Rh-catalyzed reactions of N-alkyl anilines with internal alkynes at room temperature have been developed using an in situ generated N-nitroso group as a transient oxidizing directing group. Due to mild reaction conditions, this method enabled synthesis of a broad range of N-alkyl indoles, including even two indole-based medicinal compounds. Our work disclosed the feasibility of the transient oxidizing directing group strategy in C-H functionalization reactions, which possesses the potential to enhance overall step-economy and impart new reactivity patterns to substrates.

Regioselective Nitration of N-Alkyl Anilines using tert-Butyl Nitrite under Mild Condition

Regioselective ring nitration of N-alkyl anilines is reported using tert-butyl nitrite. The reactions proceed efficiently with a wide range of substrates providing synthetically useful N-nitroso N-alkyl nitroanilines in excellent yields which can be easily converted into N-alkyl phenylenediamines and N-alkyl nitroanilines using Zn-AcOH and HCl/MeOH, respectively.

Regioselective nitration of anilines with Fe(NO3)3·9H2O as a promoter and a nitro source

An efficient Fe(NO3)3·9H2O promoted ortho-nitration reaction of aniline derivatives has been developed. This reaction may go through a nitrogen dioxide radical (NO2) intermediate, which is generated by the thermal decomposition of iron(iii) nitrate. The practicality of the present method using nontoxic and inexpensive iron reagents has been shown by the broad substrate scope and applications.

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.

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.

By-products in the rearrangement of N-methyl-N-phenylnitramine

N-Methyl-N-phenylnitramine was rearranged in the aqueous dioxane- sulphuric acid mixture to 2-nitro- and 4-nitro-N-methylanilines. The isomer ratio was independent of the acidity within the range of -0.3 > H(o) > -2.8. Some by-products were isolated and i

Observation of a single-pot aromatic reductive denitration

4,N,N-Trimethyl-3-nitrobenzenamine gave reductive denitration products (ca. 28%) upon treatment with n-butyl nitrite in the presence of catalytic amounts of ammonium chloride and water in an unprecedented one-reagent single-pot process. The three isomeric N,N-dimethylnitrobenzenamines showed the same behaviour to a much lesser extent; the ortho isomer was partially (7%) transformed into 1-methylbenzotriazole.