Benzyltriphenylphosphonium bromide
Benzyltriphenylphosphonium bromide (CAS: 1449-46-3), with the formula C6H5CH2P(Br)(C6H5)3 and a molecular weight of 433.32 g/mol, is a key phosphonium salt. It functions as a versatile Wittig reagent, essential for carbon-carbon bond formation. This compound is widely utilised in organic synthesis, particularly for olefination reactions and the stereoselective preparation of complex organic molecules.
- IUPAC
- (Phenylmethyl)triphenylphosphonium bromide,Bromo(benzyl)triphenylphosphorane,NSC 54813
- Synonyms
- (Phenylmethyl)triphenylphosphonium bromideBromo(benzyl)triphenylphosphoraneNSC 54813
Wittig Reagent for Olefination
Serves as a crucial Wittig reagent for the synthesis of alkenes from carbonyl compounds. Its reactivity allows for effective C-C bond formation in various organic transformations.
Stereoselective Synthesis
Employed in stereoselective azidolysis of vinyl epoxides and enantioselective aziridination reactions. These applications are vital for the asymmetric synthesis of complex chiral molecules.
Preparation of Pharmaceutical Intermediates
Used in the preparation of beta-amyloid plaque ligands and in the biomimetic synthesis of natural products like parvistemin A, contributing to the development of potential therapeutic agents.
Cyclopropanation Reactions
Facilitates decarboxylative cyclopropanation, a valuable method for constructing cyclopropane rings, which are important motifs in medicinal chemistry.
| Molecular weight | 433.32 |
|---|---|
| Linear formula | C6H5CH2P(Br)(C6H5)3 |
| Assay | 96% |
| Application | Reactant for:• Stereoselective azidolysis of vinyl epoxides1• Enantioselective aziridination and Friedel-Crafts cyclization for asymmetric synthesis of dihydrexidine2• Biomimetic iron(III) mediated oxidative dimerization for synthesis of benzoquinone parvistemin A3• Enantioselective sytnhesis of syn-diarylheptanoids from D-glucose4• Preparation of β-amyloid plaque ligands5• Decarboxylative cyclopropanation6 |
| Melting point | 295-298 °C(lit.) |
Hazard statements
- H315Causes skin irritation
- H319Causes serious eye irritation
- H335May cause respiratory irritation
Precautionary statements
- P261Avoid breathing dust, fume, gas or vapours
- P305IF IN EYES
| Protective equipment | dust mask type N95 (US), Eyeshields, Gloves |
|---|---|
| Water hazard class (WGK, DE) | 3 |
| Hazard codes (EU) | Xi |
| Risk statements (R) | 36/37/38 |
| Safety statements (S) | 26-36/37/39 |
Hazard information is provided for guidance. Always consult the product Safety Data Sheet (SDS), available on request, before handling.
Documentation
Every batch ships with a Certificate of Analysis covering assay, identity and purity; the grade is confirmed against your enquiry. Safety Data Sheets and technical data sheets are available on request.
Supply & logistics
Samples for technical evaluation; bulk MOQ by grade and packaging. In-stock material ships in 7–10 working days, worldwide, with full export documentation.
What is Benzyltriphenylphosphonium bromide primarily used for?
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Benzyltriphenylphosphonium bromide is primarily used as a Wittig reagent for carbon-carbon bond formation in organic synthesis, particularly for olefination reactions and stereoselective transformations.
What is the CAS number and chemical formula for Benzyltriphenylphosphonium bromide?
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The CAS number is 1449-46-3, and the chemical formula is C6H5CH2P(Br)(C6H5)3.
What grade and purity does Tech Serve Solutions supply?
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Tech Serve Solutions supplies Benzyltriphenylphosphonium bromide with an assay of 96%. This product is suitable for research and chemical synthesis and is not represented as USP, BP, or EP grade.
How should Benzyltriphenylphosphonium bromide be handled safely?
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Benzyltriphenylphosphonium bromide may cause skin irritation (H315), serious eye irritation (H319), and respiratory irritation (H335). Appropriate personal protective equipment, including a dust mask (type N95), eyeshields, and gloves, should be used. Ensure adequate ventilation and avoid dust formation.
Is Benzyltriphenylphosphonium bromide a controlled substance?
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The provided data does not indicate that Benzyltriphenylphosphonium bromide is a controlled substance.
How is Benzyltriphenylphosphonium bromide packed and shipped?
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Tech Serve Solutions exports fine chemicals globally. Specific packaging and shipping details are provided upon request to ensure compliance with all regulations.
How can I request a quote or sample?
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To request a quote or sample of Benzyltriphenylphosphonium bromide, please contact our sales team via the website or through your usual communication channels.
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