10424-92-7

Usage

Type of compound

Nitroso derivative of hydrazine

Usage

Reagent in organic synthesis

Potential applications

Medicine and agriculture

Role

Precursor in the synthesis of pharmaceuticals and agrochemicals

Chemical structure

Unique and reactive

Additional studies

Potential as a chemical intermediate in the production of dyes, pigments, and other specialty chemicals

Importance

Plays a significant role in the development of various products and processes in different industries

InChI:InChI=1/C9H11N3O2/c1-11(2)10-7-8-3-5-9(6-4-8)12(13)14/h3-7H,1-2H3/b10-7+

Upstream product

• 17271-88-4 p-nitrobenzyl azide 
• 57-14-7 N,N-Dimethylhydrazine 
• 555-16-8 4-nitrobenzaldehdye 

Downstream Products

• 6310-10-7 4-nitrobenzaldehyde hydrazone 
• 87743-89-3 4-aminobenzaldehyde N,N-dimethylhydrazone 
• 82453-72-3 N-[2-(Dimethyl-hydrazono)-2-(4-nitro-phenyl)-acetyl]-methanesulfonamide 
• 82453-74-5 (4-nitrophenyl)glyoxylic acid (4-methylphenyl-sulfonamide) N,N-dimethylhydrazone 
• 57295-53-1 1-methyl-5-(methylthio)-3-(4-nitrophenyl)-1H-1,2,4-triazole 
• 99063-63-5 1,1-Dimethyl-2-(p-aminobenzyl)hydrazin 

Relevant academic research and scientific papers

Determination of 1,1-Dimethylhydrazine in Water with High Pressure Liquid Chromatography and Spectrophotometric Detection Using Micellar Catalysis

Abstract: The possibility of improving the detection of 1,1-dimethylhydrazine (unsymmetrical dimethylhydrazine, UDMH) by HPLC-SPD under preliminary derivatization with 2-nitrobenzaldehyde (2NBA) and 4?nitrobenzaldehyde (4NBA) in water with micellar cataly

Perfluoroalkylation of Aryl-N,N-dimethyl Hydrazones Using Hypervalent Iodine(III) Reagents or Perfluoroalkyl Iodides

Radical trifluoromethylation of aryl N,N-dimethyl hydrazones using TBAI as an initiator and Togni's reagent as a trifluoromethyl radical source is described. Cascades proceed via electron-catalysis; this approach is generally more applicable to hydrazone perfluoroalkylation using perfluoroalkyl iodides as the radical precursors in combination with a base under visible-light initiation.

Synthesis of o -(dimethylamino)aryl ketones, acridones, acridinium salts, and 1 H -indazoles by the reaction of hydrazones and arynes

A novel, efficient route to biologically and pharmaceutically important o-(dimethylamino)aryl ketones, acridones, acridinium salts, and 1H-indazoles has been developed starting from readily available hydrazones of aldehydes and o-(trimethylsilyl)aryl triflates. The reaction proceeds through arynes under mild conditions, tolerates a wide range of functional groups, and provides the final products in good to excellent yields.

Synthesis of o -(dimethylamino)aryl ketones and acridones by the reaction of 1,1-dialkylhydrazones and arynes

A novel, efficient route to biologically and pharmaceutically important o-(dimethylamino)aryl ketones and acridones has been developed starting from readily available 1,1-dimethylhydrazones of aldehydes and o-(trimethylsilyl)aryl triflates. The reaction proceeds under mild conditions, tolerates a wide range of functional groups, and provides the final products in good to excellent yields.

A general one-pot, three-component mono N-alkylation of amines and amine derivatives in lithium perchlorate/diethyl ether solution

An efficient, general procedure for reductive monoalkylation of amines and amine derivatives with aldehydes is reported. Treatment of aldehydes with primary amines, secondary amines, O-trimethylsilylhydroxylamine, and N,N-dimethylhydrazine in lithium perc

A 'one-pot' procedure for the oxidative conversion of alkyl halides and tosylates to N,N-dimethylhydrazones

The treatment of a solution of an alkyl halide with sodium azide results in the formation of a solution of the alkyl azide, which upon filtration to remove the sodium halide, is treated with N,N-dimethyl hydrazine and catalytic FeCl3.6H2O under refluxing conditions. The result is a one pot conversion of an alkyl halide to an N,N-dimethyl hydrazone, a net oxidation of the halogen-bearing carbon.

Reaction of 1,1-dimethylhydrazones with propargyl bromide and 1,3-dibromopropyne

Quaternary salts of 1,1-dimethyl-1-(2-propynyl)hydrazones of acetaldehyde, benzaldehyde, 4-nitrobenzaldehyde, 2-thiophenealdehyde, 4-pyridinecarboxaldehyde and quaternary salts of 1,1-dimethyl-1-(3-bromo-2-propynyl)hydrazones of acetaldehyde and benzaldehyde were synthesized from the corresponding hydrazones, propargyl bromide, and 1,3-dibromopropyne at 20°C or at heating, with no solvent or in ether, acetonitrile, benzene.

Unsymmetrical dimethylhydrazine in phosphorylation reactions

The reaction of dialkyl hydrogen phosphites with nitrobenzaldehyde dimethylhydrazone leads to formation of compounds having a salt-like structure, while the reaction with hydrazones gives phosphonates. α-Dimethylhydrazinophosphonates were obtained by the

Aza-enamines, VIII. - Electrophilic Substitution reactions at the Azomethine C-Atom of Aldehyde Dialkylhydrazones: Vilsmeier Formylation and Consecutive Reactions

The reaction of hydrazones 1 with the Vilsmeier reagent yields 3-phenyl-1,4,5-triaza-1,3-pentadienium salts according to their aza-enamine character.Hydrolysis of 2 gives 1-phenylglyoxal 1-dialkylhydrazones 3, which rearrange in acidic media to 1-phenylglyoxal 2-dialkylhydrazones 4.Compound 3h forms the dihydropyrroloimidazole 5 in boiling ethanol.Pyrrolotriazinium salt 6 is obtained by the reaction of 1b with the isolated Vilsmeier reagent from dimethylformamide/oxalyl chloride.