(4-Carboxybutyl)triphenylphosphonium bromide Chemical Properties

Melting point:

204-207 °C(lit.)

Boiling point:

324.7-327.4℃ at 101.93-102.15kPa

bulk density

360-400kg/m3

Density 

1.371 at 20℃

vapor pressure 

0Pa at 25℃

Flash point:

195°(383°F)

storage temp. 

Store below +30°C.

solubility 

DMSO, Methanol, Water

form 

solid

color 

White to Off-White

Water Solubility 

Soluble in ethanol, methanol and soluble water. Insoluble in toluene and hexane.

Sensitive 

Hygroscopic

BRN 

3586477

InChIKey

KQJPHSBFOSLICV-UHFFFAOYSA-N

LogP

0.146

CAS DataBase Reference

17814-85-6(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36

RIDADR 

3278

WGK Germany 

3

HS Code 

29310095

MSDS

• Language:English Provider:(4-Carboxybutyl)triphenylphosphonium bromide
• Language:English Provider:SigmaAldrich
• Language:English Provider:ALFA

(4-Carboxybutyl)triphenylphosphonium bromide Usage And Synthesis

Chemical Properties

WHITE TO ALMOST WHITE CRYSTALLINE POWDER

Uses

suzuki reaction

Uses

(4-Carboxybutyl)triphenylphosphonium Bromide (cas# 17814-85-6) is a compound useful in organic synthesis.

Uses

• Used as a platform for delivery of pro-apoptotic peptides into the mitochondria of tumor cells

• Ring skeletons via ring closing metathesis and double bond migration ring closing metathesis reactions
• Methyl alkenyl quinolones as antimycobacterial agents
• Prostaglandins and their drug analogs via Gold-catalyzed Meyer-Schuster rearrangement
• Diphenylmethylpiperazines as N-type calcium channel blockers as potential therapeutic agents
• Folate receptor-specific glycinamide ribonucleotide formyltransferase (GARFTase) inhibitors with antitumor activity
• Cycloalkylidene alkanols with antileishmanial activity, via Wittig reaction

reaction suitability

reaction type: C-C Bond Formation

Synthesis

General method: 5-Bromovaleric acid (1 eq.) and triphenylphosphine (1 eq.) were dissolved in 300 mL of toluene and the reaction was refluxed under argon protection for 48 hours. Upon completion of the reaction, the mixture was cooled to room temperature and subsequently concentrated under reduced pressure. The target product 4-carboxybutyltriphenylphosphonium bromide was obtained by crystallization and purification of the residue from a suitable solvent.

References

[1] Journal of Organic Chemistry, 1999, vol. 64, # 9, p. 3196 - 3206
[2] Canadian Journal of Chemistry, 2003, vol. 81, # 6, p. 697 - 704
[3] Bioorganic and Medicinal Chemistry, 2011, vol. 19, # 1, p. 567 - 579
[4] Journal of Organic Chemistry, 1987, vol. 52, # 20, p. 4449 - 4453
[5] Journal of Medicinal Chemistry, 2017, vol. 60, # 14, p. 6353 - 6363

(4-Carboxybutyl)triphenylphosphonium bromide(17814-85-6)Related Product Information

• DICHLOROTRIPHENYLPHOSPHORANE
• Tetraphenylphosphonium bromide
• Allyl bromide
• Sodium bromate
• Tetrabutylammonium bromide
• Rocuronium bromide
• Ethidium bromide
• Triphenylphosphine hydrobromide
• Benzyltributylammonium bromide
• Methyltriphenylphosphonium bromide
• Ethyltriphenylphosphonium bromide
• Phenylmagnesium bromide
• Methyl bromide
• Butyltriphenylphosphonium bromide
• DIPHENYL-N-PROPYLPHOSPHINE
• (4-ETHOXYCARBONYLBUTYL)TRIPHENYLPHOSPHONIUM BROMIDE
• Triphenyl(propyl)phosphonium bromide
• BUTYLDIPHENYLPHOSPHINE