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Benzyltriphenylphosphonium bromide

Product NameBenzyltriphenylphosphonium bromide
CAS1449-46-3
MFC25H22BrP
MW433.32
EINECS215-908-4
MOL File1449-46-3.mol

Chemical Properties

Melting point	295-298 °C(lit.)
storage temp.	Inert atmosphere,Room Temperature
form	solid
color	White to Almost white
Water Solubility	Soluble in water.
Sensitive	Hygroscopic
BRN	3599867
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
InChIKey	WTEPWWCRWNCUNA-UHFFFAOYSA-M
SMILES	[P+](CC1C=CC=CC=1)(C1C=CC=CC=1)(C1C=CC=CC=1)C1=CC=CC=C1.[Br-]
CAS DataBase Reference	1449-46-3(CAS DataBase Reference)

Safety Information

Hazard Codes	Xi
Risk Statements	36/37/38
Safety Statements	26-36/37/39
WGK Germany	3
HazardClass	6.1
PackingGroup	III
HS Code	29319090

MSDS

Provider	Language
Benzyltriphenylphosphonium bromide	English
SigmaAldrich	English
ACROS	English
ALFA	English

Usage And Synthesis

Preparation

Benzyl triphenylphosphonium bromide is prepared by the following steps:To a solution of Ph3P (22 g, 0.084 mol) in toluene, BnBr (10 ml, 0.084 mol) was added dropwise with ice-cooling and stirred at room temperature for 2 hours. A solid was formed, which was filtered and washed with toluene and then dry pet ether to remove unreacted Ph3P. The salt was dried under vacuum (35 g, 96% yield).

Chemical Properties

WHITE CRYSTALLINE POWDER

Uses

Benzyltriphenylphosphonium bromide is used as a reactant for stereoselective azidolysis of vinyl epoxides, enantioselective aziridination and Friedel-Crafts cyclization for asymmetric synthesis of dihydrexidine, biomimetic iron(III) mediated oxidative dimerization for synthesis of benzoquinone parvistemin A, enantioselective synthesis of syn-diarylheptanoids from D-glucose, preparation of β-amyloid plaque ligands and decarboxylative cyclopropanation. It react with 4-methyl-oxetan-2-one to produce 4-hydroxy-1-phenyl-1-(triphenyl-l5-phosphanylidene)-pentan-2-one.

reaction suitability

reaction type: C-C Bond Formation

Synthesis

100-39-0

603-35-0

1449-46-3

The general procedure for the synthesis of triphenylbenzylphosphonium bromide from benzylbromide and triphenylphosphine was as follows: triphenylphosphine (7.868 g, 1.0 eq.) and benzylbromide (3.73 mL, 1.04 eq.) were dissolved in dimethylformamide (DMF) (30 mL) and the mixture was transferred to a 100 mL round bottom flask equipped with a reflux condenser. The reaction mixture was heated to reflux and kept for 1 hr and subsequently cooled to room temperature. The precipitated white crystalline solid was collected by filtration, washed with ether (100 mL) and finally dried under vacuum at 60 °C for 5 h to afford the product triphenylbenzylphosphonium bromide (12.676 g, 98% yield).

References

[1] Synthetic Communications, 2001, vol. 31, # 21, p. 3377 - 3382
[2] Journal of Organic Chemistry, 2018, vol. 83, # 7, p. 3529 - 3536
[3] Canadian Journal of Chemistry, 2004, vol. 82, # 9, p. 1365 - 1371
[4] Patent: WO2004/52823, 2004, A1. Location in patent: Page 8
[5] Organic Letters, 2013, vol. 15, # 22, p. 5650 - 5653

Benzyltriphenylphosphonium bromide

Chemical Properties

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MSDS

Usage And Synthesis

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