7293-45-0

Usage

InChI:InChI=1/C18H15N/c19-18-12-10-17(11-13-18)16-8-6-15(7-9-16)14-4-2-1-3-5-14/h1-13H,19H2

Upstream product

• 92-52-4 biphenyl 
• 622-37-7 Phenyl azide 
• 6810-26-0 4-hydroxylaminobiphenyl 
• 71-43-2 benzene 
• 100-65-2 N-Phenylhydroxylamine 
• 5122-94-1 4-biphenylboronic acid 
• 100-00-5 4-chlorobenzonitrile 

Downstream Products

• 64058-92-0 4-Acetamido-p-terphenyl 
• 102665-45-2 N-p-terphenyl-4-yl-benzenesulfonamide 
• 94459-02-6 <4-(allyloxy)benzoyloxy>-p-terfenyl 
• 78540-80-4 <2-<4-(4-methyl-5-phenyloxazol-2-yl)phenyl>-5-phenyloxazol-4-yl>ether 
• 94872-02-3 3-Nitro-4-propionylamino-p-terphenyl 
• 1233766-07-8 7-hydroxy-4-methyl-8-([1,1';4',1'']terphenyl-4-ylimino)methyl-2H-1-benzopyran-2-one 
• 1233766-17-0 6-hydroxy-4-methyl-5-([1,1';4',1'']terphenyl-4-ylimino)methyl-2H-1-benzopyran-2-one 
• 897671-75-9 bis([1,1′:4′,1”-terphenyl]-4-yl)amine 
• 1245939-49-4 C₆₁H₄₅N 
• 1580465-25-3 C₂₈H₂₁N₂⁽¹⁺⁾*Cl^(1-) 
• 897921-63-0 N-([1,1′-biphenyl]-4-yl)-[1,1′:4′,1″-terphenyl]-4-amine 

Relevant academic research and scientific papers

Simultaneous reduction of nitro- to amino-group in the palladium-catalyzed Suzuki cross-coupling reaction

An efficient method for palladium-catalyzed Suzuki cross-coupling reaction with simultaneous reduction of nitro- to amino-group has been developed. This method allows nitro-substituted aryl halides to readily react with arylboronic acids, to afford aryl substituted aniline in low to excellent yields. The reaction was catalyzed by Pd(OAc)2 (3 mol %) at 150 °C under atmospheric pressure in the presence of K2CO3 (3 equiv) in DMF/H2O (5/1).

N- and C-attacks on aromatics of phenylnitrenium ion generated from N-phenylhydroxylamine in the presence of trifluoroacetic acid containing polyphosphoric acid or trifluoroacetic anhydride

A phenylnitrenium ion formed from N-phenylhydroxylamine in the presence of trifluoroacetic acid (TFA) containing polyphosphoric acid (PPA) interacts with the counterion -O2CCF3 and the unshared electron-pair of H2O, showing Hammett's ρ values -5.2 and -4.0 for N- and C-attacks on aromatics PhX (X = H, Me, Et, Ph and Cl), respectively. The ratio N-/C-attack for this nitrenium ion is lower than for the nitrenium ion interacting with only the counterion; the latter nitrenium ion is generated by the use of trifluoroacetic anhydride (TFAA) instead of PPA or by reaction of phenyl azide with aromatics in TFA. The ratio for the former nitrenium ion is affected by the aromatic substituent X:X = Me > X = Et > X = Ph > X = H > X = OMe at 20 and 50°C. The order for X = Cl is between those of X = H and X = Ph at 20°C, but highest at 50°C. The ratio is increased by higher reaction temperature and by decreased concentration of TFA. The results are demonstrated from the mechanistic viewpoint for the nitrenium ions.

N- and C-Attacks of Phenylnitrenium Ions Generated from Phenyl Azides in the Presence of Trifluoroacetic Acid and/or Trifluoromethanesulphonic Acid

Phenylnitrenium ions were generated from phenyl azides in the presence of trifluoroacetic acid (TFA) and/or trifluoromethanesulphonic acid (TFSA).Unsubstituted phenylnitrenium ions and those with an electron-withdrawing group such as NO2 or CN undergo aromatic N-substitution, whereas those with an electron-donating group such as Me, OMe, CH2Ph, or Ph undergo C-substitution, hydrogen abstraction, and tar formation.The special character of TFA and TFSA as compared with other acids is discussed.

Aromatic Substitution by Phenylnitrenium and Naphthylnitrenium Ions formed from Phenyl Azide and 1-Azidonaphthalene in the Presence of Trifluoromethanesulphonic Acid

Aromatic N-substitution by phenylnitrenium ions generated from phenyl azide in the presence of a catalytic amount of trifluoromethanesulphonic acid gave diarylamines (in especially good yield in the reaction with biphenyl or naphthalene), whereas naphthylnitrenium ions from 1-azidonaphthalene react with benzene to afford a C-substitution product, 1-amino-4-phenylnaphthalene.

Acid-Catalyzed Reactions of N-Arylhydroxylamines and Related Compounds with Benzene. Iminium-Benzenium Ions

N-Arylhydroxylamines react with benzene in the presence of trifluoroacetic acid (TFA) at room temperature to give diphenylamines.When TFA was replaced by a strong acid, trifluoromethanesulfonic acid (TFSA), the major products were aminobiphenyls.The nature of the reaction was explored by reactions of 4-substituted phenylhydroxylamines and dialkylaniline N-oxides with benzene.Thus, it was demonstrated that the reactive intermediates are onium-benzenium dications which are trapped by benzene to give aminobiphenyls by a mechanism similar to the Friedel-Krafts alkylation.Further evidence for the proposed reaction mechanism was the observation that nitrosobenzene and azoxybenzene reacted with benzene to give analogous products in the presence of the stronger acid.