53269-48-0

Basic information

• Product Name: HISHICOLIN PX-4MB
• Synonyms: HISHICOLIN PX-4MB;Methyltri-n-butylphosphonium Bromide
• CAS NO: 53269-48-0
• Molecular Formula: Br*C₁₃H₃₀P
• Molecular Weight: 0
• Product Categories: Phosphonium Salts
• Mol File: 53269-48-0.mol
• Article Data: 4

Chemical Properties

• Appearance: /
• CAS DataBase Reference: HISHICOLIN PX-4MB(CAS DataBase Reference)
• NIST Chemistry Reference: HISHICOLIN PX-4MB(53269-48-0)
• EPA Substance Registry System: HISHICOLIN PX-4MB(53269-48-0)

Safety Data

• Hazardous Substances Data: 53269-48-0(Hazardous Substances Data)

Upstream product

• 120256-45-3 tri-n-butyl(methyl)phosphonium methyl carbonate 
• 75-16-1 methylmagnesium bromide 
• 74-83-9 methyl bromide 
• 998-40-3 tributylphosphine 
• 20515-45-1 tri(n-butyl)phosphane hydrobromide 
• 149-73-5 trimethyl orthoformate 

Downstream Products

• 29218-85-7 tri(n-butyl)-methylenephosphorane 

Relevant articles and documents

Exploring an Umpolung strategy for quaternization of phosphorus

We propose a new, potentially widely-applicable, Umpolung approach for the synthesis of quaternary phosphonium salts R3PR1 X (X = Cl, Br) from phosphine oxides R3PO. The new organic group R1 is introduced via nucleophilic attack on an intermediate halophosphonium salt using a Grignard reagent R1MgX and replaces the traditional phosphine quaternization approach. Consequently, the new method does not suffer from the limited availability of many parent phosphines and is much faster than standard quaternization.

The reaction of primary aromatic amines with alkylene carbonates for the selective synthesis of bis-N-(2-hydroxy)alkylanilines: The catalytic effect of phosphonium-based ionic liquids

At T ≥ 140 °C, different primary aromatic amines (pX-C 6H4NH2; X = H, OCH3, CH3, Cl) react with both ethylene- and propylene-carbonates to yield a chemoselective N-alkylation process: bis-N-(2-hydroxyalkyl)anilines [pX-C 6H4N(CH2CH(R)OH)2; R = H, CH 3] are the major products and the competitive formation of carbamates is substantially ruled out. At 140 °C, under solventless conditions, the model reaction of aniline with ethylene carbonate goes to completion by simply mixing stoichiometric amounts of the reagents. However, a class of phosphonium ionic liquids (PILs) such as tetraalkylphosphonium halides and tosylates turn out to be active organocatalysts for both aniline and other primary aromatic amines. A kinetic analysis monitored by 13C NMR spectroscopy, shows that bromide exchanged PILs are the most efficient systems, able to impart a more than 8-fold acceleration to the reaction. The reactions of propylene carbonate take place at a higher temperature than those of ethylene carbonate, and only in the presence of PIL catalysts. A mechanism based on the Lewis acidity of tetraalkylphosphonium cations and the nucleophilicity of halide anions has been proposed to account for both the reaction chemoselectivity and the function of the catalysts.