2719-13-3

Usage

Safety Profile

Poison by ingestion. When heatedto decomposition it emits toxic vapors of NOx.

Upstream product

• 507-09-5 thioacetic acid 
• 108-94-1 cyclohexanone 
• 64-19-7 acetic acid 
• 100-16-3 4-nitrophenylhydrazone 
• 861801-83-4 4,4-bis-[N'-(4-nitro-phenyl)-hydrazino]-pentan-2-one 
• 625-77-4 N-acetylacetamide 
• 113407-66-2 2-(4-nitrophenylhydrazino)tetrahydrofuran 
• 100-05-0 4-nitrobenzenediazonium chloride 
• 636-99-7 4-nitrophenylhydrazine hydrochloride 
• 108-24-7 acetic anhydride 
• 113407-52-6 4-Chloro-butyric acid N'-(4-nitro-phenyl)-hydrazide 
• 23460-22-2 triacetyl-(4-nitro-phenyl)-hydrazine 
• 27182-39-4 5-methyl-3-(4-nitro-phenyl)-3H-[1,3,4]oxadiazol-2-one 
• 70638-46-9 2,5-dimethyl-2-(4-nitro-phenylazo)-furan-3-one 

Downstream Products

• 27182-39-4 5-methyl-3-(4-nitro-phenyl)-3H-[1,3,4]oxadiazol-2-one 
• 13122-36-6 nitrobenzene-4-d 
• 787-64-4 2-(4-nitrophenyl)-1-benzofurane 
• 1694-20-8 trans-4-nitrostilbene 
• 857796-35-1 N'-acetyl-N-chloroacetyl-N-(4-nitro-phenyl)-hydrazine 

Relevant academic research and scientific papers

Palladium/copper-catalyzed arylation of alkenes with N′-acyl arylhydrazines

A novel ligand-free palladium/copper-catalyzed Heck-type coupling reaction of alkenes and N′-acyl arylhydrazines has been developed by using air as the terminal oxidant. This protocol features wide functional group tolerance and produces highly chemoselective and regioselective products with good to excellent yields.

Preparation, properties, and reductive alkylation of arylhydrazides

1 [-Acy]-2-arylhydrazines (1), readily obtained in high yield from the condensation of arylhydrazines and the appropriate liquid carboxylic acid (2), underwent reductive alkylation with the same or different liquid carboxylic acids (2) and NaBH4 to give 1-acyl-2-alkyl-2-arylhydrazines (3) in good to moderate yields. The carboxylic acid has both the role of supplying the entering alkyl group and of acting as solvent. Most likely, it also modifies the BH4- anion to an active reducing agent under those conditions. The 1H NMR criteria for identifying the location of acylation of hydrazines and E and Z isomers are given. The MS spectra of the prepared hydrazides were analyzed in order to identify relevant structural features leading to specific fragmentations.

PREPARATION OF N-ARYLAMINO-2-PYRROLIDONES FROM ARYLHYDRAZIDES OF γ-CHLOROBUTYRIC ACID

Intramolecular alkylation of the arylhydrazides of γ-chlorobutyric acid in the presence of sodium ethoxide leads to the formation of N-arylamino-2-pyrrolidones.The direction of the reaction is not altered by the absence of a substituent on the aniline nitrogen atom.In the case of a p-nitrophenyl-hydrazide, O-alkylation is observed.

PREPARATION OF HYDRAZIDES USING SILICON TETRACHLORIDE AS COUPLING AGENT

Silicon tetrachloride proved to be an effective reagent for the preparation of hydrazides from carboxylic acids.Yields were comparable to those obtained via N,N'-dicyclohexylcarbodiimide (DCC) and the procedure was used to synthesize some hydrazides which are difficult to obtain otherwise.

REACTION OF 2-ARYLAZO-2,5-DIMETHYL-3(2H)-FURANONES WITH AMMONIA. PREPARATION OF β-ACETYL-β-(3-AMINO-2-BUTENOYL)ARYLHYDRAZINES.

Ring opening of 2-arylazo-2,5-dimethyl-3(2H)-furanones (1a-d) with ammonia leads to previously unknown β-acetyl-β-(3-amino-2-butenoyl)arylhydrazines (3a-d).The reaction mechanism is discussed.