Benzyltriphenylphosphonium bromide 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

• Language:English Provider:Benzyltriphenylphosphonium bromide
• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS
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Benzyltriphenylphosphonium bromide 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

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

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