14987-96-3

Basic information

• Product Name: (4-Bromophenylimino)triphenylphosphorane
• Synonyms: (4-Bromophenylimino)triphenylphosphorane;(p-Bromophenylimino)triphenylphosphorane
• CAS NO: 14987-96-3
• Molecular Formula: C₂₄H₁₉BrNP
• Molecular Weight: 432.29
• Mol File: 14987-96-3.mol
• Article Data: 5

Chemical Properties

• Appearance: /
• CAS DataBase Reference: (4-Bromophenylimino)triphenylphosphorane(CAS DataBase Reference)
• NIST Chemistry Reference: (4-Bromophenylimino)triphenylphosphorane(14987-96-3)
• EPA Substance Registry System: (4-Bromophenylimino)triphenylphosphorane(14987-96-3)

Safety Data

• Hazardous Substances Data: 14987-96-3(Hazardous Substances Data)

Upstream product

• 2101-88-4 1-azido-4-bromobenzene 
• 21382-82-1 (carbethoxyethylidene)triphenylphosphorane 
• 2026-11-1 <α-(Ethoxycarbonyl)benzyliden>triphenylphosphoran 
• 6395-93-3 anilinotriphenylphosphonium bromide 
• 603-35-0 triphenylphosphine 
• 106-40-1 4-bromo-aniline 
• 485842-66-8 dimethyl 2-(4-bromoanilino)-3-(triphenylphosphoranylidene)butanedioate 
• 2325-27-1 N-phenyltriphenyliminophosphorane 
• 1100-88-5 benzyltriphenylphosphonium chloride 

Downstream Products

• 1985-12-2 4-Bromophenyl isothiocyanate 
• 2493-02-9 4-bromophenyl isocyanate 
• 93619-36-4 5,7-diphenyl-1,3,4-oxadiazolo<3,2-a>pyridinylium-2-(4-bromophenyl)aminide 
• 80607-56-3 Biphenyl-2,2'-diylketen-N-(4-bromphenyl)imin 
• 74378-47-5 C₂₅H₂₂BrNP⁽¹⁺⁾*I^(1-) 
• 93660-32-3 N-(4-Bromo-phenyl)-N'-(4-methoxy-benzyl)-N''-(2-oxo-4,6-diphenyl-2H-pyridin-1-yl)-guanidine 
• 1013643-61-2 C₃₃H₂₈BrN₂O₂PS 
• 1013643-62-3 C₄₂H₃₇BrN₃O₄PS₂ 
• 1394129-72-6 methyl ((5E)-5-[(4-bromophenyl)imino]-2,4-dioxo-3-phenylimidazolidin-1-yl)acetate 
• 1394129-70-4 (5E)-5-[(4-bromophenyl)imino]-1,3-dimethylimidazolidine-2,4-dione 
• 1394129-66-8 (5E)-5-[(4-bromophenyl)imino]-1,3-dimethyl-2-thioxoimidazolidin-4-one 
• 29376-76-9 4-bromo-N-(2,2-diphenylvinylidene)aniline 
• 21538-58-9 7-bromo-1,3-diphenyl-1,4-dihydrobenzo[e][1,2,4]triazin-4-yl 
• 1481615-38-6 N-(4-bromophenyl)-2,2,2-trifluoro-1-phenylethan-1-imine 

Relevant articles and documents

Reaction between triphenylphosphine and aromatic amines in the presence of diethyl azodicarboxylate: An efficient synthesis of aryliminophosphoranes under neutral and mild conditions

An efficient synthesis of aryliminophosphoranes is described. A mixture of an aromatic amine, diethyl azodicarboxylate and triphenylphosphine undergo a Mitsonobu type reaction at ambient temperature in dry dichloromethane to afford aryliminophosphoranes in excellent yields.

Vinyltriphenylphosphonium salt mediated serendipitous synthesis of aryliminophosphoranes

Crystalline phosphorus ylides are obtained in excellent yields from the 1:1:1 addition reaction between triphenylphosphine, dimethyl acetylenedicarboxylate and aromatic amines, such as aniline, 1-naphthylamine, p-toluidine, 4-bromoaniline, 4-nitroaniline, 4-acetylaniline, 2-aminopyridine, or 2-amino-5-bromopyridine. These stabilized phosphoranes undergo a smooth intramolecular reaction in boiling p-xylene or toluene to produce aryliminophosphoranes in excellent yields.

Stereoisomerization of Ketene Imines

Barriers to racemization in solution of the ketene imines 1a - y and X-ray structures of the ketene imines 1s and z are described.Similar to allenes all ketene imines have dihedral angles of 90 deg between the C- and N-substituents.The barriers to racemization range from 30 to 63 kJmol-1 and are lowered by electron attracting substituents on C and N.The barriers of m- and p-substituted N-arylketene imines give a linear Hammett correlation with ?- constants.N-Arylketene imines racemize through inversion at nitrogen and simultaneous rotation of the aryl group around the N - aryl bond.