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- Butyltriphenylphosphonium bromide
Butyltriphenylphosphonium bromide
PRICE INQUIRYCatalog Number
ACM1779517
Product Name
Butyltriphenylphosphonium bromide
Structure
![{[CurrentData.Name]}](https://resource.alfachemic.com/structure/1779-51-7.gif)
CAS
1779-51-7
Synonyms
(1-Butyl)triphenylphosphonium bromide
IUPAC Name
butyl(triphenyl)phosphanium;bromide;
Molecular Weight
399.3
Molecular Formula
C22H24BrP
Canonical SMILES
CCCC[P+](C1=CC=CC=C1)(C2=CC=CC=C2)C3=CC=CC=C3.[Br-]
InChI
InChI=1S/C22H24P.BrH/c1-2-3-19-23(20-13-7-4-8-14-20,21-15-9-5-10-16-21)22-17-11-6-12-18-22;/h4-18H,2-3,19H2,1H3;1H/q+1;/p-1
InChI Key
IKWKJIWDLVYZIY-UHFFFAOYSA-M
Melting Point
240-243 °C
Solubility
Soluble in chloroform and methanol
Appearance
White crystalline powder
Storage
Inert atmosphere, Room Temperature
Complexity
273
Covalently-Bonded Unit Count
2
EC Number
918-205-7
Exact Mass
398.0799
H-Bond Acceptor
1
Heavy Atom Count
24
Monoisotopic Mass
398.0799
NSC Number
59684
Rotatable Bond Count
6
Topological Polar Surface Area
0 Ų
Application
Butyltriphenylphosphonium bromide serves a multifaceted purpose in chemical synthesis and catalytic applications. This white crystalline powder is utilized as a phase-transfer catalyst in Suzuki reactions, facilitating the coupling of organic compounds. It acts as a reactant in free radical 5-exo-dig cyclization and is involved in intramolecular hydroacylalkoxylation processes. Moreover, it plays a critical role in Wittig reactions for the stereoselective synthesis of alkenes and the dimerization of α-olefins. Butyltriphenylphosphonium bromide is also employed in the alkylidenation of hydrazides for indole synthesis and assists in tandem cyclization and 1,2-thiolate shifts of nitrogen ylides. Further highlighting its versatility, this compound is used in synthesizing inhibitors of tubulin polymerization, reflecting its antimitotic and antitubulin properties, and in the creation of 3-phenylpropanoic acids, which serve as dual agonists for peroxisome proliferator-activated receptors, thus impacting the mitochondrial carnitine system.
March 22, 2025
An Indispensable Catalyst for Advanced Synthesis
Using Butyltriphenylphosphonium bromide as a PTC catalyst in our lab's Wittig reactions significantly improved yield and selectivity. Its role in synthesizing potent antimitotic agents proved highly effective and reliable.
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