CAS 50889-29-7 5-Carboxypentyl triphenylphosphonium bromide

Synonyms

(5-Carboxypentyl)(Triphenyl)Phosphonium Bromide

IUPAC Name

5-carboxypentyl(triphenyl)phosphanium;bromide

Molecular Weight

457.35

Molecular Formula

C24H26BrO2P

Canonical SMILES

C1=CC=C(C=C1)[P+](CCCCCC(=O)O)(C2=CC=CC=C2)C3=CC=CC=C3.[Br-];

InChI

JUWYRPZTZSWLCY-UHFFFAOYSA-N

InChI Key

InChI=1S/C24H25O2P.BrH/c25-24(26)19-11-4-12-20-27(21-13-5-1-6-14-21,22-15-7-2-8-16-22)23-17-9-3-10-18-23;/h1-3,5-10,13-18H,4,11-12,19-20H2;1H

Melting Point

197-201 °C

Purity

98%

Appearance

Solid

Complexity

386

Covalently-Bonded Unit Count

Exact Mass

456.085g/mol

H-Bond Acceptor

H-Bond Donor

Heavy Atom Count

Isomeric SMILES

C1=CC=C(C=C1)[P+](CCCCCC(=O)O)(C2=CC=CC=C2)C3=CC=CC=C3.[Br-]

Monoisotopic Mass

456.085g/mol

Rotatable Bond Count

Topological Polar Surface Area

37.3A^2

Application

5-Carboxypentyl triphenylphosphonium bromide serves several important purposes in various fields, particularly in medicine and pharmaceuticals. It functions as a pharmaceutical intermediate and a catalyst, contributing to the synthesis of compounds with significant therapeutic potential. This includes its role in preparing inhibitors for protein tyrosine phosphatase 1B, which hold promise for treating diabetes and obesity. Additionally, it is instrumental in the creation of folate receptor-specific glycinamide ribonucleotide formyltransferase inhibitors, which possess antitumor properties. The compound is also utilized in the synthesis of peptide nucleic acids (PNA), which are noted for their high specific activity, and is involved in the production of roseophilin via the Wittig/aldol methodology.

April 2, 2025

Exceptional Research-Grade [5-Carboxypentyl triphenylphosphonium bromide]

Worked excellently in synthesizing PTP1B inhibitors for diabetes research. The purity and consistency were outstanding, making complex reactions straightforward and reliable. Highly recommend it for pharmaceutical applications and catalyst roles.