21080-09-1

Basic information

• Product Name: N-(2-nitro-1-phenyl-ethyl)aniline
• Synonyms: N-(2-nitro-1-phenyl-ethyl)aniline
• CAS NO: 21080-09-1
• Molecular Formula: C₁₄H₁₄N₂O₂
• Molecular Weight: 242.2732
• Mol File: 21080-09-1.mol
• Article Data: 13

Chemical Properties

• Boiling Point: 412.5°Cat760mmHg
• Flash Point: 203.2°C
• Appearance: /
• Density: 1.213g/cm³
• Vapor Pressure: 5.17E-07mmHg at 25°C
• Refractive Index: 1.629
• CAS DataBase Reference: N-(2-nitro-1-phenyl-ethyl)aniline(CAS DataBase Reference)
• NIST Chemistry Reference: N-(2-nitro-1-phenyl-ethyl)aniline(21080-09-1)
• EPA Substance Registry System: N-(2-nitro-1-phenyl-ethyl)aniline(21080-09-1)

Safety Data

• Hazardous Substances Data: 21080-09-1(Hazardous Substances Data)

Usage

Synthesis Reference(s)

Journal of the American Chemical Society, 72, p. 4813, 1950 DOI: 10.1021/ja01166a510

InChI:InChI=1/C14H14N2O2/c17-16(18)11-14(12-7-3-1-4-8-12)15-13-9-5-2-6-10-13/h1-10,14-15H,11H2

Upstream product

• 75-52-5 nitromethane 
• 538-51-2 benzylidene phenylamine 
• 102-96-5 (2-nitroethenyl)benzene 
• 62-53-3 aniline 
• 100-52-7 benzaldehyde 
• 5153-67-3 nitrostyrene 

Downstream Products

• 105159-20-4 C₄₃H₄₄N₄O₄S₂ 
• 105159-28-2 N-{2-[4-(1,3-Dimethyl-2,4-dioxo-6-phenylamino-1,2,3,4-tetrahydro-pyrimidin-5-ylmethyl)-phenylamino]-2-phenyl-ethyl}-4-methyl-benzenesulfonamide 
• 105159-25-9 N-{2-[4-(6-Amino-1,3-dimethyl-2,4-dioxo-1,2,3,4-tetrahydro-pyrimidin-5-ylmethyl)-phenylamino]-2-phenyl-ethyl}-4-methyl-benzenesulfonamide 
• 105167-93-9 C₂₅H₂₆N₆O₄ 
• 97511-34-7 4-methyl-N-(2-(methyl(phenyl)amino)-2-phenylethyl)benzenesulfonamide 
• 97511-33-6 3,4-diphenyl-1-tosylimidazolidine 
• 105159-32-8 4-methyl-N-(2-phenyl-2-(phenylamino)ethyl)benzenesulfonamide 
• 102-96-5 (2-nitroethenyl)benzene 
• 100-52-7 benzaldehyde 
• 42164-54-5 N-(2-amino-1-phenylethyl)benzenamine 
• 75-52-5 nitromethane 
• 22710-00-5 N-pentyl-1-phenylmethanimine 
• 62-53-3 aniline 
• 538-51-2 benzylidene phenylamine 

Relevant articles and documents

Mechanistic Studies on the Michael Addition of Amines and Hydrazines to Nitrostyrenes: Nitroalkane Elimination via a Retro-aza-Henry-Type Process

In this article we report on the mechanistic studies of the Michael addition of amines and hydrazines to nitrostyrenes. Under the present conditions, the corresponding N-alkyl/aryl substituted benzyl imines and N-methyl/phenyl substituted benzyl hydrazones were observed via a retro-aza-Henry-type process. By combining organic synthesis and characterization experiments with computational chemistry calculations, we reveal that this reaction proceeds via a protic solvent-mediated mechanism. Experiments in deuterated methanol CD3OD reveal the synthesis and isolation of the corresponding deuterated intermediated Michael adduct, results that support the proposed slovent-mediated pathway. From the synthetic point of view, the reaction occurs under mild, noncatalytic conditions and can be used as a useful platform to yield the biologically important N-methyl pyrazoles in a one-pot manner, simple starting with the corresponding nitrostyrenes and the methylhydrazine.

Synthesis, Characterization and Catalytic Application of MCM 41 Supported Phenanthrolinium Dibromide Catalyst for Aza-Michael Addition Reaction in Aqueous Medium

Abstract: MCM-41 immobilized phenanthrolinium dibromide (phen-MCM-Br2) was easily prepared and applied as an efficient heterogeneous catalyst for aza-Michael addition of aromatic amines to α,β-unsaturated nitriles and nitro compounds in water. The catalyst was characterized by CHN, TGA, FT-IR, SEM, EDAX, XRD, BET, and TEM. It could be simply recovered and reused several times without significant loss of catalytic activity. Graphical Abstract: [Figure not available: see fulltext.]

Conjugate addition nitro-Mannich reaction of carbon and heteroatom nucleophiles to nitroalkenes

The conjugate addition nitro-Mannich reactions of ethyl-β-nitroacrylate (1) and β-nitrostyrene (2) with electron rich aromatic nucleophiles, stabilized carbanions, alcohols, amines, thiols, and diphenyl phosphine oxide were investigated. The one pot conju