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Benzyltriphenylphosphonium bromide

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Catalog Number

ACM1449463

Product Name

Structure

CAS

1449-46-3

Product Overview
Usage

Synonyms

(Phenylmethyl)triphenylphosphonium bromide

IUPAC Name

benzyl(triphenyl)phosphanium;bromide;

Molecular Weight

433.32

Molecular Formula

C25H22PBr

Canonical SMILES

C1=CC=C(C=C1)C[P+](C2=CC=CC=C2)(C3=CC=CC=C3)C4=CC=CC=C4.[Br-];

InChI

InChI=1S/C25H22P.BrH/c1-5-13-22(14-6-1)21-26(23-15-7-2-8-16-23,24-17-9-3-10-18-24)25-19-11-4-12-20-25;/h1-20H,21H2;1H/q+1;/p-1;

InChI Key

WTEPWWCRWNCUNA-UHFFFAOYSA-M;

Purity

99%

Complexity

347

Covalently-Bonded Unit Count

EC Number

215-908-4

Exact Mass

432.064g/mol

H-Bond Acceptor

Heavy Atom Count

Monoisotopic Mass

432.064g/mol

NSC Number

54813

Physical State

Off-white solid

Rotatable Bond Count

Topological Polar Surface Area

0A^2

Application

Benzyltriphenylphosphonium bromide serves as a versatile white crystalline powder primarily utilized in various chemical reactions and synthetic processes. It plays a crucial role in stereoselective azidolysis of vinyl epoxides, enantioselective aziridination, and Friedel-Crafts cyclization, which are important for the asymmetric synthesis of dihydrexidine. Additionally, it is involved in biomimetic iron(III) mediated oxidative dimerization for creating benzoquinone parvistemin A and in the enantioselective synthesis of syn-diarylheptanoids from D-glucose. This compound is also used in preparing β-amyloid plaque ligands and facilitating decarboxylative cyclopropanation. Furthermore, it reacts with 4-methyl-oxetan-2-one to yield 4-hydroxy-1-phenyl-1-(triphenyl-l5-phosphanylidene)-pentan-2-one.

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CAS
Size
Purity
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1449-46-3
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99%
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