29608-75-1

Basic information

• Product Name: 2-Phenyl-4-nitroaniline
• Synonyms: 2-Amino-5-nitrobiphenyl;2-Phenyl-4-nitroaniline;5-NITRO-2-BIPHENYLAMINE;5-Nitro-biphenyl-2-ylamine
• CAS NO: 29608-75-1
• Molecular Formula: C₁₂H₁₀N₂O₂
• Molecular Weight: 214.22
• Mol File: 29608-75-1.mol
• Article Data: 3

Chemical Properties

• Melting Point: 125 °C
• Boiling Point: 412.5°Cat760mmHg
• Flash Point: 203.3°C
• Appearance: /
• Density: 1.268g/cm³
• Vapor Pressure: 5.15E-07mmHg at 25°C
• Refractive Index: 1.65
• PKA: 0.22±0.10(Predicted)
• CAS DataBase Reference: 2-Phenyl-4-nitroaniline(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Phenyl-4-nitroaniline(29608-75-1)
• EPA Substance Registry System: 2-Phenyl-4-nitroaniline(29608-75-1)

Safety Data

• Hazardous Substances Data: 29608-75-1(Hazardous Substances Data)

Usage

Synthesis Reference(s)

Journal of the American Chemical Society, 73, p. 2438, 1951 DOI: 10.1021/ja01150a009

InChI:InChI=1/C12H10N2O2/c13-12-7-6-10(14(15)16)8-11(12)9-4-2-1-3-5-9/h1-8H,13H2

Upstream product

• 91330-60-8 2-azido-5-nitrobiphenyl 
• 1516-60-5 4-nitrophenyl azide 
• 71-43-2 benzene 

Downstream Products

• 845895-92-3 nicotinic acid-(5-nitro-biphenyl-2-ylamide) 
• 489409-86-1 2-bromo-5-nitro-1,1'-biphenyl 
• 115984-97-9 N,N'-biphenyl-2,5-diyl-bis-benzenesulfonamide 
• 412337-52-1 2-nitro-6-phenyl-phenanthridine 
• 107527-50-4 N,N'-Di-<5-nitro-2-biphenylyl>-adipamid 
• 323191-91-9 2-phenyl-4-[3-S-(tert-butoxycarbonyl)mercaptobenzoyl]amino-3'-carboxybiphenyl 
• 112330-67-3 7-methoxy-9-phenyl-5H-pyrido<3,2-c>azepine 
• 112330-66-2 6-azido-8-phenylquinoline 
• 3077-85-8 3-Nitro-carbazol 
• 855641-24-6 4-(2-nitro-phenanthridin-6-yl)-aniline 
• 29608-76-2 2-chloro-5-nitro-1,1'-biphenyl 
• 1330574-18-9 ethyl 2-(5,6-dihydro-2-nitro-5-tosylphenanthridin-6-yl)acetate 

Relevant articles and documents

INTER- AND INTRA-MOLECULAR AROMATIC N-SUBSTITUTION BY ARYLNITRENIUM-ALUMINIUM CHLORIDE COMPLEXES GENERATED FROM ARYL AZIDES IN THE PRESENCE OF ALUMINIUM CHLORIDE

Reactions of phenyl azide with aromatic compounds ( i. e. benzene, toluene, ethylbenzene, cumene, anisole, and bromobenzene ) in the presence of AlCl3 gave diarylamines, whwreas those of phenyl azides with an electron-donating group such as Me and OMe yield little of the corresponding diarylamines ( tarformation takes place ).The reaction of 4-nitrophenyl azide with benzene in the presence of AlCl3 gave 4-nitrophenyl(phenyl)amine and a C-substitution product, 2-amino-5-nitrobiphenyl.Decomposition of 2-azidophenyl(phenyl)methane and 2-azidobiphenyls in CH2Cl2 in the presence of AlCl3 underwent an N-cyclization to afford 9,10-dihydroacridine and carbazoles, respectively, in good yields.The kinetic data on the decomposition of aryl azides and a Hammet plot ( with p= -6.0 ) for the formation of diarylamines suggest that the products are formed by an aromatic N-substitution of arylnitrenium-AlCl3 complexes via azide-AlCl3 complexes.We further argue the character of arylnitrenium-AlCl3 complexes.

Cyclisation of 2-Azidodiphenylmethane and 2-Azidobiphenyls by Regiospecyfic N-Attack of Arylnitrenium-Aluminium Chloride Complexes

Decomposition of 2-azidodiphenylmethane and 2-azidobiphenyls in CH2Cl2 in the presence of AlCl3 gave 9,10-dihydroacridine and carbazoles, respectively, in reasonable yields by regiospecific N-attack of an arylnitrenium-AlCl3 complex.