10151-95-8

Basic information

• Product Name: NITROACETANILIDE
• Synonyms: NITROACETANILIDE;2-Nitro-N-phenylacetamide
• CAS NO: 10151-95-8
• Molecular Formula: C₈H₈N₂O₃
• Molecular Weight: 180.16
• Mol File: 10151-95-8.mol
• Article Data: 5

Chemical Properties

• Melting Point: 94°C
• Boiling Point: 312.97°C (rough estimate)
• Appearance: /
• Density: 1.4190
• Refractive Index: 1.6000 (estimate)
• CAS DataBase Reference: NITROACETANILIDE(CAS DataBase Reference)
• NIST Chemistry Reference: NITROACETANILIDE(10151-95-8)
• EPA Substance Registry System: NITROACETANILIDE(10151-95-8)

Safety Data

• Hazardous Substances Data: 10151-95-8(Hazardous Substances Data)

Upstream product

• 98071-48-8 N-Isopropyliden-nitroacethydrazid 
• 62-53-3 aniline 
• 25854-38-0 sodium nitromethane 
• 103-71-9 phenyl isocyanate 
• 71-43-2 benzene 
• 141377-54-0 2-nitro-1-phenylethan-1-ol 
• 625-75-2 nitroacetic acid 
• 6061-03-6 nitroacetyl chloride 
• 101-99-5 N-carboethoxyaniline 
• 102721-78-8 1-(N-arylamino)-1-methylthio-2-nitroethane 

Downstream Products

• 56-40-6 glycine 
• 102026-04-0 2-nitro-5-oxo-5-phenyl-valeric acid anilide 
• 91567-55-4 5-ethoxy-4,5-dihydro-isoxazole-3-carboxylic acid anilide 
• 54614-93-6 (2-nitro-phenyl)-carbamic acid tert-butyl ester 
• 1613073-78-1 N³,N⁶-diphenyl-1,4,2,5-dioxadiazine-3,6-dicarboxamide 
• 73025-54-4 (Z)-1-Anilino-2-nitro-1-phenylethylene 

Relevant articles and documents

Copper-Catalyzed N-Arylation of Nitroenamines with Diaryliodonium Salts

A novel synthetic methodology was developed for the N-arylation of nitroenamine derivatives utilizing diaryliodonium triflates and copper(I) chloride as a catalyst. The procedure enables the easy aryl transfer from the hypervalent species under mild catalytic conditions with unusual heteroatom preference and high efficiency.

Stereoselective control in the Staudinger reactions involving monosubstituted ketenes with electron acceptor substituents: Experimental investigation and theoretical rationalization

The stereoselectivity of the Staudinger reactions involving monosubstituted ketenes with electron acceptor substituents was investigated experimentally by determination of the product stereochemistry and theoretically via DFT calculations. The results indicate that imines preferentially attack the less sterically hindered exo-side of the ketenes to generate zwitterionic intermediates. Subsequently, for cyclic imines, the intermediates undergo a conrotatory ring closure directly to produce β-lactams, while for linear imines, the imine moiety of the intermediates isomerizes to more stable intermediates, which further undergo a conrotatory ring closure to afford trans-β-lactams. The steric hindrance and the isomerization, rather than the torquoelectronic effect, play crucial roles in controlling the stereoselectivity in the practical Staudinger reactions involving monosubstituted ketenes with electron acceptor substituents, although the unaccessible borylketene with a powerful electron acceptor group controls the stereoselectivity torquoelectronically, in theory.

Production of carbonyl compounds substituted in α-position

Production of carbonyl compounds substituted in the α-position and having the formula: EQU1 wherein R1 is alkyl, aralkyl, phenyl, toluyl, naphthyl, alkoxy or amino; R2 is hydrogen EQU2 A is hydrogen, alkyl, halo or EQU3 R6 is hydrogen or methyl, and R11 is alkyl; wherein said compounds are formed by reacting a sulfur ylide having the formula: EQU4 wherein Y is the radical EQU5 and R9 and R10 are alkyl or phenyl, with a solution containing both an electrophilic agent A' that is converted into the radical A and a nucleophilic agent B' that is converted into the radical B. The resulting carbonyl compounds are useful as starting materials for the production of paper, textile, and leather auxiliaries, plant protection agents, alkyd resins, polyesters and polyamides.