(5-Carboxypentyl)triphenylphosphonium bromide

Base Information

• Chemical Name: (5-Carboxypentyl)triphenylphosphonium bromide
• CAS No.: 50889-29-7
• Molecular Formula: C24H26O2P. Br
• Molecular Weight: 457.347
• Hs Code.: 2931599090
• DSSTox Substance ID: DTXSID80381364
• ChEMBL ID: CHEMBL4286465
• Mol file: 50889-29-7.mol

Synonyms:50889-29-7;(5-Carboxypentyl)triphenylphosphonium bromide;(5-carboxypentyl)(triphenyl)phosphonium bromide;5-Carboxypentyl triphenylphosphonium bromide;(5-carboxypentyl)triphenylphosphanium bromide;5-carboxypentyl(triphenyl)phosphanium;bromide;(5-Carboxypentyl) triphenyl phosphonium bromide;Phosphonium, (5-carboxypentyl)triphenyl-, bromide;MFCD00055556;(5-Carboxyamyl)triphenylphosphonium Bromide;(5-Carboxypentyl)triphenylphosphoniumBromide;SCHEMBL711677;CHEMBL4286465;DTXSID80381364;JUWYRPZTZSWLCY-UHFFFAOYSA-N;PXJVNUUWRJUMAQ-UHFFFAOYSA-M;AKOS015961316;MG-0025;AC-13548;AC-31791;SY032896;5-Carboxypentyltriphenylphosphonium Bromide;5-carboxypentyl triphenylphosphorane bromide;5-carboxypentyl-triphenylphosphonium bromide;5-carboxypentyltriphenyl phosphonium bromide;C3113;FT-0620194;(5-carboxy-pentyl)triphenylphosphonium bromide;(5-carboxypentyl)-triphenylphosphonium bromide;Triphenyl (5-carboxypentyl)phosphonium bromide;(5-carboxy-l-pentyl)triphenylphosphonium bromide;EN300-7362026;J-501561;(6-hydroxy-6-oxo-hexyl)-triphenyl-phosphonium bromide

Chemical Property of (5-Carboxypentyl)triphenylphosphonium bromide

Chemical Property:

• Appearance/Colour: white crystalline solid
• Melting Point: 200-202 ºC
• PSA: 50.89000
• LogP: 1.62950
• Storage Temp.: Inert atmosphere,Room Temperature
• Sensitive.: Hygroscopic
• Solubility.: Soluble in Chloroform and Methanol.
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 9
• Exact Mass: 456.08538
• Heavy Atom Count: 28
• Complexity: 386

Purity/Quality:

98%, ^*data from raw suppliers

(5-Carboxypentyl)triphenylphosphonium Bromide ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xi,Xn
• Statements: 36/37/38-20/21/22
• Safety Statements: 26-36-36/37/39-22

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C(C=C1)[P+](CCCCCC(=O)O)(C2=CC=CC=C2)C3=CC=CC=C3.[Br-]
• Uses: (5-Carboxypentyl)(triphenyl)phosphonium bromide is used in medicine and as pharmaceutical intermediate. It is also employed as catalyst. Reactant for: Preparation of inhibitor of protein tyrosine phosphatase 1B for treatment of diabetes and obesity. Synthesis of folate receptor-specific glycinamide ribonucleotide formyltransferase inhibitors with antitumor activity. Preparation of peptide nucleic acids (PNA) with high specific activity. Synthesis of roseophilin via Wittig/aldol methodology. It is used in medicine and as pharmaceutical intermediate. It is also employed as catalyst.

Technology Process of (5-Carboxypentyl)triphenylphosphonium bromide

There total 12 articles about (5-Carboxypentyl)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: 100.0%

6-bromohexanoic acid (4224-70-8) + triphenylphosphine (603-35-0) → (5-carboxypentyl)triphenylphosphonium bromide (50889-29-7)

Guidance literature:

In acetonitrile; for 16h; Heating;

DOI:10.1021/jo00107a009

Reference yield: 100.0%

6-bromohexanoic acid (4224-70-8) → (5-carboxypentyl)triphenylphosphonium bromide (50889-29-7)

Guidance literature:

With triphenylphosphine; In toluene; at 120 ℃; for 17h;

DOI:10.1016/j.tet.2018.08.049

Reference yield: 92.0%

hexahydro-2H-oxepin-2-one (502-44-3,24980-41-4,80137-66-2) + triphenylphosphine hydrobromide (6399-81-1) → (5-carboxypentyl)triphenylphosphonium bromide (50889-29-7)

Guidance literature:

at 160 ℃; for 1h;

DOI:10.1248/cpb.45.685

upstream raw materials:

6-bromohexanoic acid

triphenylphosphine

hexahydro-2H-oxepin-2-one

triphenylphosphine hydrobromide

Downstream raw materials:

-(3,6,7,8,9,10-Hexahydro-10-oxo-2H-thiecin-3-yl)-(phenylmethyl)carbamoyl azide

(Z)-(R)-9-{[1-Phenyl-meth-(E)-ylidene]-amino}-3,4,5,6,9,10-hexahydro-thiecin-2-one

(Z)-(R)-8-Amino-9-benzylsulfanyl-non-6-enoic acid methyl ester

(Z)-(R)-8-Benzylamino-9-benzylsulfanyl-non-6-enoic acid methyl ester

Refernces

• 1、 Sodano, Federica,Rolando, Barbara,Spyrakis, Francesca,Failla, Mariacristina,Lazzarato, Loretta,Gazzano, Elena,Riganti, Chiara,Fruttero, Roberta,Gasco, Alberto,Sortino, Salvatore. "Tuning the Hydrophobicity of a Mitochondria-Targeted NO Photodonor". . p. 1238 - 1245. Retrieved 2018.
• 2、 González-Gil, Inés,Zian, Debora,Vázquez-Villa, Henar,Hernández-Torres, Gloria,Martínez, R. Fernando,Khiar-Fernández, Nora,Rivera, Richard,Kihara, Yasuyuki,Devesa, Isabel,Mathivanan, Sakthikumar,Del Valle, Cristina Rosell,Zambrana-Infantes, Emma,Puigdomenech, María,Cincilla, Giovanni,Sanchez-Martinez, Melchor,Rodríguez De Fonseca, Fernando,Ferrer-Montiel, Antonio V.,Chun, Jerold,López-Vales, Rubén,López-Rodríguez, María L.,Ortega-Gutiérrez, Silvia. "A Novel Agonist of the Type 1 Lysophosphatidic Acid Receptor (LPA1), UCM-05194, Shows Efficacy in Neuropathic Pain Amelioration". supporting information. p. 2372 - 2390. Retrieved 2020/01/02.