(3-CARBOXYPROPYL)TRIPHENYLPHOSPHONIUM BROMIDE Chemical Properties

Melting point:

244-247 °C(lit.)

storage temp. 

Inert atmosphere,Room Temperature

form 

Crystalline Powder, Crystals, or Flakes

color 

White

Water Solubility 

Soluble in water. soluble in ethanol.

Sensitive 

Hygroscopic

BRN 

4173599

InChI

InChI=1S/C22H21O2P.BrH/c23-22(24)17-10-18-25(19-11-4-1-5-12-19,20-13-6-2-7-14-20)21-15-8-3-9-16-21;/h1-9,11-16H,10,17-18H2;1H

InChIKey

NKVJKVMGJABKHV-UHFFFAOYSA-N

SMILES

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

CAS DataBase Reference

17857-14-6(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36

WGK Germany 

3

Hazard Note 

Irritant/Hygroscopic

HS Code 

29319090

MSDS

• Language:English Provider:ACROS
• Language:English Provider:SigmaAldrich
• Language:English Provider:ALFA

(3-CARBOXYPROPYL)TRIPHENYLPHOSPHONIUM BROMIDE Usage And Synthesis

Chemical Properties

White powder and granules

Uses

suzuki reaction

Uses

(3-Carboxypropyl)triphenylphosphonium Bromide is a reagent used in the preparation of sphingosine 1-phosphate-1 receptor antagonists. Also used in the synthesis of mitochondrial vitamin E metabolites and other mitochondrial targets in the study of mitochodrial functions. Also used in the preparation of benzosuberene analogs that inhibit tubulin assembly and demonstrate cytotoxicity.

Uses

(3-Carboxypropyl)triphenylphosphonium bromide is used as antimalarial agents, antimycobacterial agents,antifungal agents, inhibitors of protein tyrosine phosphatase.

reaction suitability

reaction type: C-C Bond Formation

Synthesis

General procedure: 4-Bromobutyric acid (1 eq.) and triphenylphosphine (1 eq.) were dissolved in 300 mL of toluene under argon protection and heated to reflux for 48 hours. Upon completion of the reaction, the mixture was cooled to room temperature and subsequently concentrated under reduced pressure to remove the solvent. The target product (3-propylcarboxy)triphenylphosphonium bromide was obtained by crystallization and purification of the residue from a suitable solvent.

References

[1] Bioorganic and Medicinal Chemistry, 2011, vol. 19, # 1, p. 567 - 579
[2] Bioorganic and Medicinal Chemistry, 2016, vol. 24, # 21, p. 5088 - 5102
[3] Zeitschrift fur Naturforschung - Section B Journal of Chemical Sciences, 2002, vol. 57, # 3, p. 335 - 337
[4] Tetrahedron Letters, 2016, vol. 57, # 10, p. 1083 - 1086
[5] Journal of the American Chemical Society, 2018, vol. 140, # 17, p. 5805 - 5813

(3-CARBOXYPROPYL)TRIPHENYLPHOSPHONIUM BROMIDE(17857-14-6)Related Product Information

• [3-(ETHOXYCARBONYL)PROPYL]TRIPHENYLPHOSPHONIUM BROMIDE
• (4-BROMOBENZYL)TRIPHENYLPHOSPHONIUM BROMIDE
• (5-Carboxypentyl)(triphenyl)phosphonium bromide
• (4-Carboxybutyl)triphenylphosphonium bromide
• 2-(ETHOXYCARBONYL)ETHYLTRIPHENYLPHOSPHONIUM BROMIDE
• TRIMETHYLENEBIS(TRIPHENYLPHOSPHONIUM BROMIDE)
• TETRAMETHYLENEBIS(TRIPHENYLPHOSPHONIUM BROMIDE)
• PENTAMETHYLENEBIS(TRIPHENYLPHOSPHONIUM BROMIDE)
• ETHYLENEBIS(TRIPHENYLPHOSPHONIUM BROMIDE)
• TRI-N-BUTYLPHOSPHINE OXIDE
• (2-CARBOXYETHYL)TRIPHENYLPHOSPHONIUM BROMIDE
• TETRAPHENYLPHOSPHONIUM IODIDE
• 2-(1,3-Dioxolan-2-yl)ethyltriphenylphosphonium bromide
• (1,3-Dioxolan-2-ylmethyl)triphenylphosphonium bromide
• Benzotriazole-1-yl-oxytripyrrolidinophosphonium hexafluorophosphate
• Triphenyl(propyl)phosphonium bromide
• (3-CARBOXYPROPYL)TRIPHENYLPHOSPHONIUM BROMIDE
• (3-CARBOXYPROPYL-D6)TRIPHENYLPHOSPHONIUM BROMIDE