(3-Carboxypropyl)triphenylphosphonium bromide

Base Information

• Chemical Name: (3-Carboxypropyl)triphenylphosphonium bromide
• CAS No.: 17857-14-6
• Molecular Formula: C22H22BrO2P
• Molecular Weight: 429.293
• Hs Code.: 29319090
• European Community (EC) Number: 629-007-2
• DSSTox Substance ID: DTXSID70443905
• ChEMBL ID: CHEMBL4289887
• Mol file: 17857-14-6.mol

Synonyms:17857-14-6;(3-Carboxypropyl)triphenylphosphonium bromide;3-Carboxypropyltriphenylphosphonium bromide;3-carboxypropyl triphenylphosphonium bromide;MFCD00274196;3-carboxypropyl(triphenyl)phosphanium;bromide;Phosphonium, (3-carboxypropyl)triphenyl-, bromide;Phosphonium, (3-carboxypropyl)triphenyl-, bromide (1:1);(3-carboxypropyl)triphenylphosphanium bromide;SCHEMBL484781;CHEMBL4289887;(4-HYDROXY-4-OXOBUTYL)TRIPHENYLPHOSPHONIUM BROMIDE;DTXSID70443905;NKVJKVMGJABKHV-UHFFFAOYSA-N;XFZDCVIYHHHYBQ-UHFFFAOYSA-M;BCP04353;AKOS015833005;GC10171;AS-10669;SY109349;(3-carboxypropyl)triphenylphosphine bromide;(Carboxypropyl)triphenylphosphonium bromide;(3-carboxypropy)triphenylphosphonium bromide;3-carboxypropyltriphenyl phosphonium bromide;3-(Carboxypropyltriphenyl)phosphonium bromide;C1635;FT-0604704;FT-0615285;(3-carboxy-propyl)triphenylphosphonium bromide;(3-Carboxypropyl)-triphenylphosphonium bromide;(3-carboxypropyl)triphenyl-phosphonium bromide;(3-Carboxypropyl)(triphenyl)phosphanium bromide;(3-carboxypropyl)(triphenyl)phosphonium bromide;F10044;EN300-7562858;J-501196;(3-CARBOXYPROPYL)TRIPHENYLPHOSPHANIUM BROMIDE;(3-CARBOXYPROPYL)TRIPHENYLPHOSPHONIUM BROMIDE;CARBOXYPROPYLTRIPHENYLPHOSPHONIUMBROMIDE;(3-CARBOXYPROPYL)TRIPHENYLPHOSPHONIUM BROMIDE(3-CARBOXYPROPYL)TRIPHENYLPHOSPHONIUM BROMIDE

Chemical Property of (3-Carboxypropyl)triphenylphosphonium bromide

Chemical Property:

• Appearance/Colour: White powder and granules
• Melting Point: 244-247 °C(lit.)
• PSA: 50.89000
• LogP: 0.84930
• Storage Temp.: Inert atmosphere,Room Temperature
• Sensitive.: Hygroscopic
• Water Solubility.: Soluble in water. soluble in ethanol.
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 7
• Exact Mass: 428.05408
• Heavy Atom Count: 26
• Complexity: 359

Purity/Quality:

99% ^*data from raw suppliers

(3-Carboxypropyl)triphenylphosphonium Bromide ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C(C=C1)[P+](CCCC(=O)O)(C2=CC=CC=C2)C3=CC=CC=C3.[Br-]
• Uses: suzuki reaction (3-Carboxypropyl)triphenylphosphonium bromide is used as antimalarial agents, antimycobacterial agents,antifungal agents, inhibitors of protein tyrosine phosphatase. (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.

Technology Process of (3-Carboxypropyl)triphenylphosphonium bromide

There total 3 articles about (3-Carboxypropyl)triphenylphosphonium bromide which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 94.0%

4-butanolide (96-48-0) + triphenylphosphine hydrobromide (6399-81-1) → (3-carboxypropyl)(triphenyl)phosphonium bromide (17857-14-6)

Guidance literature:

at 160 ℃; for 1h;

DOI:10.1248/cpb.45.685

Reference yield: 92.0%

bromobutyric acid (2623-87-2) + triphenylphosphine (603-35-0) → (3-carboxypropyl)(triphenyl)phosphonium bromide (17857-14-6)

Guidance literature:

In toluene; for 48h; Inert atmosphere; Reflux;

DOI:10.1016/j.bmc.2010.10.060

Reference yield:

→ (3-carboxypropyl)(triphenyl)phosphonium bromide (17857-14-6)

Guidance literature:

upstream raw materials:

4-butanolide

triphenylphosphine hydrobromide

bromobutyric acid

triphenylphosphine

Downstream raw materials:

5-(2,2-diphenylcyclopropyl)-4-pentenoic acid

5-m-tolyl-pent-4-enoic acid

5-(2,3-dichloro-phenyl)-pent-4-enoic acid

5,5-diphenyl-4-pentenoic acid

Refernces

• 1、 Wei, Guoqing,Wang, Yi,Huang, Xuehui,Yang, Guang,Zhao, Jingya,Zhou, Shaobing. "Induction of mitochondrial apoptosis for cancer therapy: Via dual-targeted cascade-responsive multifunctional micelles". . p. 8137 - 8147. Retrieved 2018.
• 2、 Constant-Urban, Céline,Charif, Mounia,Goffin, Eric,Van Heugen, Jean-Claude,Elmoualij, Bena?ssa,Chiap, Patrice,Mouithys-Mickalad, Ange,Serteyn, Didier,Lebrun, Philippe,Pirotte, Bernard,De Tullio, Pascal. "Triphenylphosphonium salts of 1,2,4-benzothiadiazine 1,1-dioxides related to diazoxide targeting mitochondrial ATP-sensitive potassium channels". . p. 5878 - 5881. Retrieved 2013.
• 3、 -. "Triphenylphosphine modification-based mitochondrion targeted melatonin as well as preparation method and application thereof". Paragraph 0051-0056. . Retrieved 2021/02/10.
• 4、 Centeno-Pedrazo, A.,Freixa, Z.,Garcia-Suarez, E. J.,Perez-Arce, J.,Prieto-Fernandez, S.. "Phosphonium-based ionic liquids: Economic and efficient catalysts for the solvent-free cycloaddition of CO2 to epoxidized soybean vegetable oil to obtain potential bio-based polymers precursors". . . Retrieved 2021/10/01.