3-Carboxypropyltriphenylphosphonium bromide
[CAS# 17857-14-6]

Identification

• Classification: Organic raw materials >> Organic phosphine compound
• Name: 3-Carboxypropyltriphenylphosphonium bromide
• Synonyms: (3-Carboxypropyl)triphenylphosphonium bromide
• Molecular Formula: C₂₂H₂₂BrO₂P
• Molecular Weight: 429.29
• CAS Registry Number: 17857-14-6
• EC Number: 629-007-2
• SMILES: C1=CC=C(C=C1)[P+](CCCC(=O)O)(C2=CC=CC=C2)C3=CC=CC=C3.[Br-]

Properties

• Melting point: 244-247 °C

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H315-H319-H335
• Safety Statements: P261-P264-P264+P265-P271-P280-P302+P352-P304+P340-P305+P351+P338-P319-P321-P332+P317-P337+P317-P362+P364-P403+P233-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Skin irritation	Skin Irrit.	2	H315
Eye irritation	Eye Irrit.	2	H319
Specific target organ toxicity - single exposure	STOT SE	3	H335
Eye irritation	Eye Irrit.	2A	H319

Discovery and Applications

3-Carboxypropyltriphenylphosphonium bromide is an important compound in organophosphorus chemistry, notable for its applications in organic synthesis and biological studies. The compound was synthesized by reacting triphenylphosphine with 3-carboxypropyl bromide, forming a phosphonium salt with distinctive properties due to the presence of a carboxypropyl group attached to the phosphorus center through a bromide counterion.

The molecular structure of 3-Carboxypropyltriphenylphosphonium bromide includes a triphenylphosphine group bonded to a carboxypropyl moiety. The carboxyl group introduces additional reactivity and functionality, which is beneficial for further chemical transformations. This phosphonium salt is soluble in polar solvents, making it versatile for various chemical applications.

One of the primary uses of 3-Carboxypropyltriphenylphosphonium bromide is as a reagent in organic synthesis. It serves as a key intermediate for preparing phosphonium-based ligands and catalysts. These ligands are integral to several catalytic processes, including cross-coupling reactions and asymmetric synthesis. The carboxyl group in the phosphonium salt allows for further modification, leading to the development of complex and functionalized phosphine ligands that are crucial for various synthetic applications.

In addition to its synthetic applications, 3-Carboxypropyltriphenylphosphonium bromide has notable uses in biological and medicinal chemistry. Phosphonium salts, including this compound, are known to interact with biological membranes, which makes them useful in studying cellular uptake and distribution. The carboxypropyl group in the compound can engage in biochemical interactions, offering potential in drug design and development.

The compound also finds applications in the preparation of phosphonium-based probes for imaging and detection purposes. These probes are employed to visualize cellular and molecular processes, which is valuable for understanding biochemical and physiological phenomena. The combination of the phosphonium salt's unique properties and its reactivity makes it a versatile tool in both chemical and biological research.

The significance of 3-Carboxypropyltriphenylphosphonium bromide extends beyond its synthesis and immediate applications. Its ability to participate in various chemical transformations and its role in biological studies highlight its importance as a multifunctional compound. Ongoing research and development may uncover additional applications and improvements in the synthesis and use of this phosphonium salt, expanding its impact in the fields of chemistry and biology.

References

2022. A Mitochondria-Targeted Phenylbutyric Acid Prodrug Confers Drastically Improved Anticancer Activities. Journal of Medicinal Chemistry.
DOI: https://pubmed.ncbi.nlm.nih.gov/35818137

2018. Rational design of mitochondria-targeted pyruvate dehydrogenase kinase 1 inhibitors with improved selectivity and antiproliferative activity. European Journal of Medicinal Chemistry.
DOI: https://pubmed.ncbi.nlm.nih.gov/29890389