59285-66-4

Basic information

• Product Name: iodure de triphenyl N,N-dimethylaminophosphonium
• Synonyms: iodure de triphenyl N,N-dimethylaminophosphonium
• CAS NO: 59285-66-4
• Molecular Weight: 433.272
• Mol File: 59285-66-4.mol
• Article Data: 4

Chemical Properties

• CAS DataBase Reference: iodure de triphenyl N,N-dimethylaminophosphonium(CAS DataBase Reference)
• NIST Chemistry Reference: iodure de triphenyl N,N-dimethylaminophosphonium(59285-66-4)
• EPA Substance Registry System: iodure de triphenyl N,N-dimethylaminophosphonium(59285-66-4)

Safety Data

• Hazardous Substances Data: 59285-66-4(Hazardous Substances Data)

Upstream product

• 17986-01-5 N-methyl-P,P,P-triphenylphosphine imide 
• 74-88-4 methyl iodide 
• 34257-63-1 N-methyl-N-phenylaminotriphenylphosphonium iodide 
• 124-40-3 dimethyl amine 
• 1034-39-5 dibromotriphenylphosphorane 
• 15729-44-9 amino(triphenyl)phosphonium chloride 
• 13916-35-3 lithium triphenylphosphonium azayldiide 
• 2240-47-3 imino(triphenyl)phosphorane 
• 603-35-0 triphenylphosphine 
• 15931-69-8 bromure de triphenyl aminophosphonium 

Downstream Products

• 63207-50-1 Bis(dimethylamino)carbenium Iodide 
• 100-61-8 N-methylaniline 
• 124-40-3 dimethyl amine 
• 90709-21-0 N,N-dimethylaminotriphenylphosphonium tribromide 

Relevant articles and documents

Phosphorus in organic synthesis. The tanigawa reaction revisited as a method for converting alcohols to tertiary amines

Contrary to earlier observations, N-methyl-N- phenylaminotriphenylphosphonium iodide 1 (the Murahashi reagent) does not react with alcohols and primary or secondary amines under mild conditions (80°) to give secondary or tertiary amines. However the reaction can be successfully performed at higher temperatures. A mechanistic scheme implying initial amine exchange between 1 and the added amine leading to the N,N- dimethyl analog 5 is suggested. An improved synthesis where the reactive intermediate 5 is formed in situ from triphenylphosphine, carbon tetrachloride and HNR3R4 is described.

Alkylation et acylation de la triphenylphosphinimine N-lithiee

A new synthetic approach to primary and secondary amines using N-lithiated triphenylphosphinimine is reported.This key reagent, accessible in two steps from dibromortiphenylphosphorane and ammonia, when treated with electrophiles yields N-substituted triphenylphosphinimine derivatives.These can react to give N-mono or disubstituted triphenylphosphonium salts which upon hydrolysis lead to the corresponding primary and secondary amines.