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Butyltriphenylphosphonium bromide

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Catalog Number

ACM1779517

Product Name

Butyltriphenylphosphonium bromide

Structure

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CAS

1779-51-7

Product Overview
Usage

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 Å²

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.

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