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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
Storage Class	11 - Combustible Solids
Hazard Classifications	Eye Irrit. 2 Skin Irrit. 2 STOT SE 3

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

Preparation Products And Raw materials

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