18992-13-7

Usage

Synthesis Reference(s)

The Journal of Organic Chemistry, 50, p. 1699, 1985 DOI: 10.1021/jo00210a600

InChI:InChI=1/C4H6N2O2/c1-4(2,3-5)6(7)8/h1-2H3

Upstream product

• 78-67-1 2,2'-azobis(isobutyronitrile) 
• 5234-64-0 2-hydroxyamino-2-methylpropanenitrile 
• 44513-62-4 2-cyano-2-nitrosopropane 
• 513-81-5 2,3-dimethyl-buta-1,3-diene 
• 71-43-2 benzene 
• 41658-69-9 2-bromo-2-methyl-propionitrile 
• 79-46-9 2-nitropropane 
• 143-33-9 sodium cyanide 
• 460-19-5 ethanedinitrile 
• 151-50-8 potassium cyanide 
• 594-71-8 2-chloro-2-nitro-propane 
• 5447-97-2 2-bromo-2-nitropropane 
• 595-49-3 2,2-dinitropropane 
• 19355-69-2 2-amino-2-cyanopropane 

Downstream Products

• 460-19-5 ethanedinitrile 
• 29770-62-5 α,α-dimethyl-β-nitroisovaleronitrile 
• 41727-22-4 2-Hexinnitril 
• 29770-63-6 1-(α-cyanoisopropyl)-1-nitrocyclohexane 
• 33695-62-4 2-methyl-2-phenylsulfanylpropanenitrile 

Relevant academic research and scientific papers

Free Radical Pathways in the Nitrous Acid Deamination of α-Aminonitriles

Free radicals and carbocations are generated competitively in nitrous acid deamination reactions of α-aminonitriles: in the absence of added scavengers the radicals are trapped by NO2 and by NO.

2-Substituted nitrones and isomeric hydroxylamines - obtained via aluminium amalgam reduction of nitro nitriles and ketones-a new access to convenient intermediates for nitroso carbonyl compounds preparation

Substituted five-membered cyclic nitrones (pyrroline N-oxides) have been obtained in good to high yields from tertiary γ-nitro ketones and nitriles employing aluminium amalgam as a reducing agent in moist diethyl ether or THF. Attempts to obtain cyclic amino nitrones from α- or β-nitro nitriles failed and only the corresponding hydroxylamines have been isolated. Both nitrones and hydroxylamines have been used for synthesis of tertiary C-nitroso nitriles or ketones.

Electrooxidative coupling of salts of nitro compounds with halide, nitrite, cyanide, and phenylsulfinate anions

Electrolysis of salts of primary and secondary nitro compounds (nitroethane, 1- and 2-nitropropanes, nitrocyclohexane, and nitrocycloheptane) in the presence of excess halide, nitrite, cyanide, and phenylsulfinate anions under undivided and divided amperostatic electrolysis conditions in a two-phase medium (CH2Cl2/H2O) produces geminal nitrohalides (35-85% yields), dinitro compounds (15-51%), nitronitriles (6-27%), and nitrosulfones (50-70%). The salts of secondary nitro compounds form the products of oxidative coupling with halide and phenylsulfinate anions under the undivided electrolysis conditions. In all other cases, divided electrolysis is required.

Preparation of α-Nitronitriles

α-Bromonitro compounds react readily with sodium cyanide in bipolar aprotic solvents giving α-nitronitriles in good yields.

Reaction of Nitronate Salts with Cyanogen

Nitronate salts react with cyanogen yielding mainly geminal nitronitriles.

Catalyzed Oxidative Nitration of Nitronate Salts

Nitronate salts are converted to gem-dinitro compounds with nitrite ion and persulfate, in the presence of a catalytic amount of ferricyanide.The use of cyanide or sulfinate salts in place of nitrile gave gem-cyanonitro compounds and α-nitro sulfones, respectively.

Oxidative Substitution of Nitroparaffin Salts

α,α-Dinitro compounds, α-nitro sulfones, and α-nitro nitriles are obtained in excellent yields when nitroparaffin salts are coupled to nitrite, benzenesulfinate, and cyanide ions by the agency of potassium ferricyanide.