trans-2-Phenylvinylboronic acid pinacol ester
trans-2-Phenylvinylboronic acid pinacol ester (CAS: 83947-56-2) is an organoboron compound with the linear formula C6H5CH=CHBO2C2(CH3)4 and a molecular weight of 230.11 g/mol. This ester serves as a versatile reactant in various organic synthesis applications. It is particularly useful in oxidative coupling, cycloaddition, and palladium-catalyzed Heck reactions, enabling the preparation of complex organic molecules. Available from Tech Serve Solutions, it is a key intermediate for advanced chemical research and development.
- IUPAC
- (E)-4,4,5,5-Tetramethyl-2-(2-phenylvinyl)-1,3,2-dioxaborolane,(E)-4,4,5,5-Tetramethyl-2-styryl-1,3,2-dioxaborolane,4,4,5,5-Tetramethyl-2-((E)-2-phenylethenyl)-1,3,2-dioxaborolane,trans-2-Styreneboronic acid pinacol ester,trans-2-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)styrene
- Synonyms
- (E)-4,4,5,5-Tetramethyl-2-(2-phenylvinyl)-1,3,2-dioxaborolane(E)-4,4,5,5-Tetramethyl-2-styryl-1,3,2-dioxaborolane4,4,5,5-Tetramethyl-2-((E)-2-phenylethenyl)-1,3,2-dioxaborolanetrans-2-Styreneboronic acid pinacol estertrans-2-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)styrene
Oxidative Coupling Reactions
This pinacol ester acts as a reactant in oxidative coupling reactions catalysed by areneruthenium complexes, facilitating carbon-carbon bond formation.
Cycloaddition Reactions
It is employed as a substrate in various cycloaddition reactions, contributing to the synthesis of cyclic organic compounds with defined stereochemistry.
Allyl Vinyl Ether Synthesis
Utilised in copper-catalysed coupling reactions with alcohols, this boronate ester enables the preparation of allyl vinyl ethers.
Synthesis of Pyridinecarbonitriles
It serves as a precursor for the preparation of 5-vinyl-3-pyridinecarbonitriles, which have been investigated as potential PKCθ inhibitors.
Diastereoselective Additions
The compound participates in diastereoselective additions to zincated hydrazones, allowing for stereospecific trapping of boron/zinc bimetallic intermediates.
Palladium-Catalyzed Oxidative Heck Reactions
It is a reactant in regioselective and stereoselective Pd-catalyzed chelate-controlled intermolecular oxidative Heck reactions, important for constructing complex molecular architectures.
| Molecular weight | 230.11 |
|---|---|
| Linear formula | C6H5CH=CHBO2C2(CH3)4 |
| Application | Reactant for:• Oxidative coupling reactions catalyzed by areneruthenium1• Cycloaddition reactions2• Preparation of allyl vinyl ethers via Cu-catalyzed coupling with alcohols3• Preparation of 5-vinyl-3-pyridinecarbonitriles as PKCθ inhibitors4• Diastereoselective addition to zincated hydrazones and stereospecific trapping of boron/zinc bimetallic intermediates by carbon electrophiles5• Regioselective and stereoselective Pd-catalyzed chelate-controlled intermolecular oxidative Heck reactions6 |
| Melting point | 27-33 °C(lit.) |
| Protective equipment | Eyeshields, Gloves |
|---|---|
| Flash point | >110 °C / >230 °F |
| 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 trans-2-Phenylvinylboronic acid pinacol ester used for?
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trans-2-Phenylvinylboronic acid pinacol ester is used as a reactant in various organic synthesis applications, including oxidative coupling reactions, cycloaddition reactions, preparation of allyl vinyl ethers, synthesis of 5-vinyl-3-pyridinecarbonitriles, diastereoselective additions to zincated hydrazones, and regioselective and stereoselective Pd-catalyzed oxidative Heck reactions.
What is the CAS number and formula for trans-2-Phenylvinylboronic acid pinacol ester?
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The CAS number is 83947-56-2, and its linear formula is C6H5CH=CHBO2C2(CH3)4.
What grade and purity does Tech Serve Solutions supply?
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Tech Serve Solutions supplies this compound as a research or technical grade chemical. We do not represent it as USP, BP, EP, or any other pharmacopoeia grade unless explicitly stated in the product specifications.
How should trans-2-Phenylvinylboronic acid pinacol ester be handled safely?
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When handling trans-2-Phenylvinylboronic acid pinacol ester, it is essential to wear eyeshields and gloves. This compound has a flash point above 110 °C (230 °F) and is classified under WGK Germany 3. Ensure adequate ventilation and avoid contact with skin and eyes.
Is trans-2-Phenylvinylboronic acid pinacol ester a controlled substance?
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Based on the provided data, trans-2-Phenylvinylboronic acid pinacol ester is not listed as a controlled substance.
How is this chemical shipped and exported by Tech Serve Solutions?
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Tech Serve Solutions is a global supplier and exporter of fine chemicals. This product can be packed and shipped internationally according to regulatory requirements. Please contact us for specific shipping and export details.
How can I request a quote or sample for trans-2-Phenylvinylboronic acid pinacol ester?
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To request a quote or a sample, please visit the Tech Serve Solutions website or contact our sales department directly. Provide the product name and CAS number (83947-56-2) for prompt service.
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