Butyltriphenylphosphonium bromide Chemical Properties

Melting point:

240-243 °C(lit.)

storage temp. 

Inert atmosphere,Room Temperature

solubility 

Chloroform, Methanol

form 

Crystalline Powder

color 

White

Water Solubility 

soluble

Sensitive 

Hygroscopic

BRN 

3580224

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

InChIKey

IKWKJIWDLVYZIY-UHFFFAOYSA-M

SMILES

[P+](CCCC)(C1C=CC=CC=1)(C1C=CC=CC=1)C1=CC=CC=C1.[Br-]

CAS DataBase Reference

1779-51-7(CAS DataBase Reference)

EPA Substance Registry System

Phosphonium, butyltriphenyl-, bromide (1779-51-7)

Safety Information

Hazard Codes 

Xn

Risk Statements 

21/22-36/37/38

Safety Statements 

36/37-36/37/39-26

RIDADR 

3464

WGK Germany 

3

RTECS 

TA1855200

TSCA 

TSCA listed

HazardClass 

6.1

PackingGroup 

III

HS Code 

29319090

MSDS

• Language:English Provider:Butyltriphenylphosphonium bromide
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Butyltriphenylphosphonium bromide Usage And Synthesis

Chemical Properties

white crystalline powder

Uses

suzuki reaction

Uses

Reactant for: Free radical 5-exo-dig cyclization Intramolecular hydroacylalkoxylation Wittig reactions for stereoselective synthesis of alkenes Dimerization of α-olefins Alkylidenation of hydrazides for synthesis of indoles Tandem cyclization and 1,2-thiolate shift of nitrogen ylides

Uses

n-Butyltriphenylphosphonium Bromide is used in the synthesis of inhibitors of tubulin polymerization thus expressing antimitotic and antitubulin properties. Also used in the synthesis of 3-phenylpropanoic acids as peroxisome proliferator-activated receptor dual agonists affecting the mitochondrial carnitine system.

Uses

PTC catalyst

reaction suitability

reaction type: C-C Bond Formation

Synthesis

Under nitrogen protection, 280 g of bromobutane and 696 g of triphenylphosphine were added to a 2 L four-neck flask dissolved in 500 mL of xylene. The reaction mixture was heated to reflux temperature with continuous stirring for 6 hours. After completion of the reaction, the system was cooled to room temperature, the precipitated white crystals were collected by filtration and washed with xylene. After drying, 797 g of butyltriphenylphosphonium bromide was obtained as a white solid in 97.7% yield.

References

[1] Patent: JP6136589, 2017, B2. Location in patent: Paragraph 0102-0104
[2] Acta Chimica Hungarica, 1987, vol. 124, # 5, p. 737 - 748
[3] Journal of Fluorine Chemistry, 2002, vol. 113, # 2, p. 177 - 183
[4] Pharmazie, 1999, vol. 54, # 1, p. 26 - 30
[5] Synthetic Communications, 1981, vol. 11, # 2, p. 125 - 132

Butyltriphenylphosphonium bromide(1779-51-7)Related Product Information

• Diethylene glycol monobutyl ether
• Allyl bromide
• Triphenylphosphine
• Sodium bromate
• Tetrabutylphosphonium bromide
• Triphenylphosphine hydrobromide
• Tributylphosphine
• Methyltriphenylphosphonium bromide
• Ethidium bromide
• Tetraphenylphosphonium bromide
• Ethyltriphenylphosphonium bromide
• Triphenylphosphine oxide
• Butyl acetate
• Buprofezin
• Benzyltributylammonium bromide
• Cyhalofop-butyl
• Tris(triphenylphosphine)chlororhodium
• Rocuronium bromide