(Benzyloxycarbonylmethyl)triphenylphosphonium bromide
(Benzyloxycarbonylmethyl)triphenylphosphonium bromide (CAS: 78385-36-1) is a Wittig reagent with the molecular formula C6H5CH2O2CCH2P(C6H5)3Br and a molecular weight of 493.37. This chemical plays a role in various synthetic transformations, particularly in carbon-carbon bond formation. It is a valuable tool for organic chemists engaged in the synthesis of complex molecules, including unsaturated carbonyl compounds and phosphonic acid derivatives.
Stereoselective Wittig Olefination
This reagent facilitates the stereoselective preparation of α,β-unsaturated carbonyl compounds through Wittig olefination reactions with aldehydes. These reactions can be performed under solventless conditions or using ultrasonication for enhanced efficiency.
Synthesis of Phosphonic Acids
It is employed in the Wittig reaction for the synthesis of [difluoro(alkenylphenyl)methyl]phosphonic acids, which have been explored as inhibitors of protein tyrosine phosphatase 1B (PTP-1B).
Aza-Morita-Baylis-Hillman Reactions
The compound serves as a reactant in atypical aza-Morita-Baylis-Hillman mechanisms, contributing to novel synthetic pathways.
Thermal Decomposition Studies
Its thermal decomposition properties have been investigated, providing insights into the stability and breakdown mechanisms of such phosphonium salts.
Double Aza-Michael Reactions
This reagent is utilized in the context of double aza-Michael reactions, allowing for the construction of more complex molecular architectures.
| Molecular weight | 493.37 |
|---|---|
| Linear formula | C6H5CH2O2CCH2P(C6H5)3Br |
| Assay | 97% |
| Application | Reactant for:• Atypical aza-Morita-Baylis-Hillman mechanism1• Thermal decomposition2• Double aza-Michael reaction3• Cyclodextrin derivatives4• Stereoselective preparation of α,β-unsaturated carbonyl compounds via stereoselective Wittig olefination with aldehydes under solventless conditions or ultrasonication5• Synthesis of [difluoro(alkenylphenyl)methyl]phosphonic acids on non-crosslinked polystyrene as inhibitors of PTP-1B via Wittig reaction6 |
| Melting point | 124 °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 (Benzyloxycarbonylmethyl)triphenylphosphonium bromide used for?
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(Benzyloxycarbonylmethyl)triphenylphosphonium bromide is used as a Wittig reagent in organic synthesis, particularly for the stereoselective preparation of α,β-unsaturated carbonyl compounds and in the synthesis of phosphonic acid derivatives. It also serves as a reactant in atypical aza-Morita-Baylis-Hillman mechanisms and double aza-Michael reactions.
What is the CAS number and molecular formula for (Benzyloxycarbonylmethyl)triphenylphosphonium bromide?
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The CAS number is 78385-36-1, and the molecular formula is C6H5CH2O2CCH2P(C6H5)3Br.
What grade and purity does Tech Serve Solutions supply?
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Tech Serve Solutions supplies (Benzyloxycarbonylmethyl)triphenylphosphonium bromide with an assay of 97%. This is a research-grade chemical and is not represented as USP, BP, EP, or any pharmacopoeia grade.
How should (Benzyloxycarbonylmethyl)triphenylphosphonium bromide be handled safely?
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This compound is classified as a Warning with hazards including skin irritation (H315), serious eye irritation (H319), and respiratory irritation (H335). When handling, wear a dust mask (type N95 or equivalent), safety eyeglasses, and gloves. Ensure good ventilation and avoid inhaling dust. In case of eye contact, rinse cautiously with water for several minutes and seek medical advice.
Is this product available for international export?
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Yes, Tech Serve Solutions is a specialist global supplier and exporter of fine chemicals, including (Benzyloxycarbonylmethyl)triphenylphosphonium bromide. We can arrange for its export worldwide.
How can I request a sample or quote?
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To request a sample or a quote for (Benzyloxycarbonylmethyl)triphenylphosphonium bromide, please contact our sales department through the website or by phone, providing your contact details and the quantity required.
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