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4-Carboxybutyl triphenylphosphonium bromide
PRICE INQUIRYCatalog Number
ACM17814856
Product Name
4-Carboxybutyl triphenylphosphonium bromide
Structure
![{[CurrentData.Name]}](https://resource.alfachemic.com/structure/17814-85-6.gif)
CAS
17814-85-6
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
2
EC Number
241-782-5
Exact Mass
442.07g/mol
H-Bond Acceptor
3
H-Bond Donor
1
Heavy Atom Count
27
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
8
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!
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