Benzyl(triphenylphosphoranylidene)acetate
Benzyl(triphenylphosphoranylidene)acetate (CAS: 15097-38-8) is a chemical compound with the linear formula (C6H5)3P=CHCO2CH2C6H5 and a molecular weight of 410.44. It serves as a versatile reagent, primarily employed in various synthetic organic chemistry applications, including C-C bond formation and olefination reactions. This Wittig reagent is a key component in the synthesis of complex organic molecules.
- IUPAC
- (Benzyloxycarbonylmethylene)triphenylphosphorane,2-(Triphenylphosphoranylidene)acetic acid phenylmethyl ester
Vinylic Wittig Reactions
This compound acts as a reactant in tributylphosphine-mediated vinylogous Wittig reactions, facilitating the formation of specific carbon-carbon double bonds.
Synthesis of Bioactive Compounds
It is utilized in the synthesis of 1,2-dioxanes, which have demonstrated antitrypanosomal activity, highlighting its role in medicinal chemistry research.
Organocatalysis and Cycloadditions
The reagent participates in organocatalytic Michael-type reactions and Wittig reactions involving phosphorus ylides. It also plays a role in stereoselective phosphine-catalyzed cycloadditions to construct spirocyclopenteneoxindoles.
Enantioselective Synthesis
Benzyl(triphenylphosphoranylidene)acetate is employed in enantioselective synthetic pathways, such as the synthesis of pantothenic acid.
Preparation of Phosphorus Ylides
It is a precursor in the preparation of phosphorus ylides through reactions with reagents like acetic anhydride.
| Molecular weight | 410.44 |
|---|---|
| Linear formula | (C6H5)3P=CHCO2CH2C6H5 |
| Assay | 97% |
| Application | Reactant for: • Tributylphosphine-mediated vinylogous Wittig reactions1• Synthesis of 1,2-dioxanes for antitrypanosomal activity2• Organocatalytic Michael-type reactions / Wittig reactions of phosphorus ylides and unsaturated ketones3• Stereoselective phosphine-catalyzed cycloaddition to form spirocyclopenteneoxindoles4• Enantioselective synthesis of pantothenic acid5• Preparation of phosphorus ylides from phosphoranes and acetic anhydride6 |
| Melting point | 120-122 °C(lit.) |
| Protective equipment | Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter |
|---|---|
| Water hazard class (WGK, DE) | 3 |
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 Benzyl(triphenylphosphoranylidene)acetate used for?
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Benzyl(triphenylphosphoranylidene)acetate is used as a reactant in vinylogous Wittig reactions, the synthesis of 1,2-dioxanes with antitrypanosomal activity, organocatalytic Michael-type and Wittig reactions, stereoselective cycloadditions, enantioselective synthesis of pantothenic acid, and the preparation of phosphorus ylides.
What are the CAS number and formula for Benzyl(triphenylphosphoranylidene)acetate?
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The CAS number is 15097-38-8 and the linear formula is (C6H5)3P=CHCO2CH2C6H5.
What grade and purity does Tech Serve Solutions supply?
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Tech Serve Solutions supplies Benzyl(triphenylphosphoranylidene)acetate with an assay of 97%. This product is supplied for research and technical purposes and is not represented as USP, BP, EP, or other pharmacopoeial grades.
What are the safety and handling precautions for Benzyl(triphenylphosphoranylidene)acetate?
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Handling Benzyl(triphenylphosphoranylidene)acetate requires appropriate personal protective equipment, including eyeshields and gloves. A type N95 (US) or type P1 (EN143) respirator filter should be used. Consult the Safety Data Sheet for detailed handling and hazard information. It is classified with WGK Germany 3.
How is Benzyl(triphenylphosphoranylidene)acetate packed and shipped?
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Benzyl(triphenylphosphoranylidene)acetate is carefully packed and exported by Tech Serve Solutions, adhering to all necessary regulations for chemical transport.
How can I request a quote or sample of Benzyl(triphenylphosphoranylidene)acetate?
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To request a quote or a sample of Benzyl(triphenylphosphoranylidene)acetate, please contact the Tech Serve Solutions sales team via our website or listed contact information.
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