6092-74-6

Basic information

• Product Name: N-[(1E)-1-(4-chlorophenyl)-3-hydrazinyl-3-oxoprop-1-en-2-yl]benzamide
• CAS NO: 6092-74-6
• Molecular Formula: C₁₄H₁₃NO₃
• Molecular Weight: 315.7543
• Mol File: 6092-74-6.mol
• Article Data: 6

Chemical Properties

• Density: 1.335g/cm³
• Refractive Index: 1.659
• CAS DataBase Reference: N-[(1E)-1-(4-chlorophenyl)-3-hydrazinyl-3-oxoprop-1-en-2-yl]benzamide(CAS DataBase Reference)
• NIST Chemistry Reference: N-[(1E)-1-(4-chlorophenyl)-3-hydrazinyl-3-oxoprop-1-en-2-yl]benzamide(6092-74-6)
• EPA Substance Registry System: N-[(1E)-1-(4-chlorophenyl)-3-hydrazinyl-3-oxoprop-1-en-2-yl]benzamide(6092-74-6)

Safety Data

• Hazardous Substances Data: 6092-74-6(Hazardous Substances Data)

Upstream product

• 98-95-3 nitrobenzene 
• 501-53-1 benzyl chloroformate 
• 1157855-07-6 benzyl N-phenyl-N-(benzoxycarbonyloxy)carbamate 
• 3426-71-9 Benzyl N-hydroxycarbamate 
• 1483-73-4 diphenyliodonium bromide 
• 100-65-2 N-Phenylhydroxylamine 
• 84447-15-4 phenylhydroxylamine oxalate 

Downstream Products

• 81803-90-9 benzyl 2-benzyl-1H-indole-1-carboxylate 
• 371-40-4 4-fluoroaniline 
• 1161512-86-2 C₁₉H₂₁NO₃ 
• 1095280-68-4 2-(Cbz-amino)phenyl 4-toluenesulfonate 
• 1095280-66-2 2-(Cbz-amino)phenyl methanesulfonate 
• 65440-92-8 (2-Benzyloxycarbonylaminophenyl)oxalessigsaeuredimethylester 
• 76570-51-9 N-benzyloxycarbonyl-N-phenyl-O-methylhydroxylamine 
• 131424-24-3 methyl 1-carbobenzyloxyindole-3-carboxylate 
• 81617-45-0 {2-[Ethyl-(4-nitro-benzoyl)-amino]-phenyl}-carbamic acid benzyl ester 
• 81803-87-4 N-benzoyloxycarbonyl-2-(phenylacetoacetyl)aniline 
• 81617-44-9 {2-[Methyl-(4-nitro-benzoyl)-amino]-phenyl}-carbamic acid benzyl ester 
• 91075-20-6 2-Benzenesulfonylmethyl-indole-1-carboxylic acid benzyl ester 

Relevant articles and documents

Regioselective installation of fluorosulfate (-OSO2F) functionality into aromatic C(sp2)-H bonds for the construction of: Para-amino-arylfluorosulfates

The construction of para-amino-arylfluorosulfates was achieved through installation of fluorosulfate (-OSO2F) functionality into aromatic C(sp2)-H bonds by the reaction of N-arylhydroxylamine with sulfuryl fluoride (SO2Fs

Facile procedure for the synthesis of N-aryl-N-hydroxy carbamates

An efficient one-pot procedure for the zinc-mediated reduction of nitroarenes in the presence of chloroformates leading to the corresponding N,O-bisprotected hydroxylamine is described. Reactions proceed smoothly under ambient conditions in THF-water mixt

Meldrum's Acid in Organic Synthesis. VI. Synthesis of 2-Substituted Indoles from Acyl Meldrum's Acids and Phenylhydroxylamine via Sigmatropic Rearrangement

Phenylhydroxylamine (13) oxalate was quite easily acylacetylated by heating with an equimolar amount of acyl Meldrum's acid (4) in acetonitrile to give an N-acylacetylphenylhydroxylamine (14) in high yield.When 14 was treated with another equimolar amount of the same 4 in refluxing toluene, a series of reactions, O-acylacetylation, 1-aza-1'-oxasigmatropic rearrangement, decarboxylation, dehydrative cyclization, and deacylation, occured consecutively to give a 2-substituted indole (16) in fair yield, though sometimes accompanied by the formation of a 5-substituted 4-isoxazolin-3-one (17).N-Benzoyl, N-acetyl, and N-benzyloxycarbonyl derivatives of phenylhydroxylamine (18) were treated with phenylacetyl Meldrum's acid (4i) in refluxing benzene containing copper powder to give readily rearranged ortho alkylation products (19), which were converted to the corresponding N-acyl-2-benzylindoles (20) by treatment with hydrochloric acid in boiling ethanol or with anhydrous p-toluenesulfonic acid in benzene at room temperature.Keywords - acyl Meldrum's acid; phenylhydroxylamine; N-acylacetylphenylhydroxylamine; 2-substituted indole; 1-aza-1'-oxasigmatropic rearrangement; acid-catalyzed cyclization