CAS 17814-85-6 4-Carboxybutyl triphenylphosphonium bromide

Synonyms

5-(Triphenylphosphonio)pentanoic acid bromide; Carboxybutyltriphenylphosphonium bromide

IUPAC Name

4-carboxybutyl(triphenyl)phosphanium;bromide

Molecular Weight

443.32

Molecular Formula

C23H24O2PBr

Canonical SMILES

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

InChI

MLOSJPZSZWUDSK-UHFFFAOYSA-N

InChI Key

InChI=1S/C23H23O2P.BrH/c24-23(25)18-10-11-19-26(20-12-4-1-5-13-20,21-14-6-2-7-15-21)22-16-8-3-9-17-22;/h1-9,12-17H,10-11,18-19H2;1H

Melting Point

204-207 °C(lit.)

Flash Point

383 °F

Purity

98%

Appearance

Solid

Storage

Refrigerator

Complexity

372

Covalently-Bonded Unit Count

EC Number

241-782-5

Exact Mass

442.07g/mol

H-Bond Acceptor

H-Bond Donor

Heavy Atom Count

Isomeric SMILES

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

Monoisotopic Mass

442.07g/mol

NSC Number

147756

Rotatable Bond Count

Topological Polar Surface Area

37.3A^2

Application

4-Carboxybutyl triphenylphosphonium bromide serves as a versatile compound in organic synthesis, functioning primarily as a platform for delivering pro-apoptotic peptides to the mitochondria of cancer cells. This compound dons the form of a white to nearly white crystalline powder and is instrumental in diverse chemical reactions and preparations. Among its applications, it acts as a reactant in forming ring skeletons through ring-closing metathesis and double bond migration reactions. It also aids in synthesizing methyl alkenyl quinolones with antimycobacterial properties and generating prostaglandins and related drug analogs via gold-catalyzed Meyer-Schuster rearrangement. Additionally, it contributes to the development of diphenylmethylpiperazines, potential therapeutics functioning as N-type calcium channel blockers, and folate receptor-specific glycinamide ribonucleotide formyltransferase (GARFTase) inhibitors with antitumor activity. Furthermore, it assists in the production of cycloalkylidene alkanols with antileishmanial efficacy via the Wittig reaction.

March 20, 2025

Exceptional Reagent for Complex Synthesis

Using 4-Carboxybutyl triphenylphosphonium bromide from Alfa Chemistry in our research, we successfully synthesized complex organic frameworks. The white crystalline powder was integral for efficient Suzuki reactions, aiding in pro-apoptotic peptide delivery studies. Highly recommend for organic synthesis tasks!