(3-Trimethylsilyl-2-propynyl)triphenylphosphonium bromide
(3-Trimethylsilyl-2-propynyl)triphenylphosphonium bromide (CAS 42134-49-6), with the empirical formula C24H26BrPSi and a molecular weight of 453.43 g/mol, is a specialised phosphonium salt. It functions as a valuable reagent in organic synthesis, particularly for carbon-carbon bond formation. Its applications span stereoselective and regioselective Wittig reactions, Horner-Wadsworth-Emmons olefination, and aromatic ring umpolung, making it a key component in complex molecule construction.
Wittig and Horner-Wadsworth-Emmons Olefination
This phosphonium salt serves as a reactant in stereoselective and regioselective Wittig reactions, as well as Horner-Wadsworth-Emmons olefination. These processes are crucial for the formation of carbon-carbon double bonds.
Aromatic Ring Umpolung
The compound facilitates aromatic ring umpolung, a synthetic strategy that reverses the normal polarity of an aromatic system, enabling novel reaction pathways and functionalisation.
Bromoetherification Reactions
It is employed as a reactant in bromoetherification reactions, contributing to the synthesis of cyclic ethers through intramolecular cyclisation.
Olefination of Garner's Aldehyde
The reagent is specifically useful for the olefination of Garner's aldehyde, a key intermediate in amino acid synthesis, enabling the introduction of vinyl functionalities.
| Molecular weight | 453.43 |
|---|---|
| Empirical formula | C24H26BrPSi |
| Assay | 98% |
| Application | Reactant for:• Horner-Wadsworth-Emmons olefination1• Aromatic ring umpolung2• Stereoselective Wittig reaction3• Bromoetherification reactions4• Olefination of Garner′s aldehyde5• Regioselective Wittig reaction6 |
| Melting point | 166-167 °C (dec.)(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 |
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 (3-Trimethylsilyl-2-propynyl)triphenylphosphonium bromide used for?
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It is used as a reactant in various organic synthesis reactions, including Horner-Wadsworth-Emmons olefination, aromatic ring umpolung, stereoselective and regioselective Wittig reactions, bromoetherification reactions, and the olefination of Garner's aldehyde.
What is the CAS number and formula for this compound?
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The CAS number is 42134-49-6 and the empirical formula is C24H26BrPSi.
What grade and purity does Tech Serve Solutions supply?
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Tech Serve Solutions supplies this chemical with an assay of 98%. It is suitable for research and general synthetic applications. TSS does not represent this product as USP, EP, BP, or any other pharmacopoeia grade.
How should (3-Trimethylsilyl-2-propynyl)triphenylphosphonium bromide be handled safely?
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This compound is a Warning substance that causes skin irritation (H315), serious eye irritation (H319), and may cause respiratory irritation (H335). When handling, wear a dust mask type N95 (US), eyeshields, and gloves. Ensure adequate ventilation.
How is this chemical packed and shipped by TSS?
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Tech Serve Solutions exports this chemical globally. Specific packaging details are available upon request, ensuring compliance with international shipping regulations for hazardous materials.
How can I request a sample or quote?
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To request a sample or a detailed quote, please contact our sales department through the website or by phone, providing your specific requirements and shipping details.
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