Vinylboronic acid pinacol ester
Vinylboronic acid pinacol ester (CAS 75927-49-0, C8H15BO2, MW 154.01) is a versatile organoboron reagent. It is a key intermediate in organic synthesis, notably employed in various palladium-catalyzed cross-coupling reactions like Suzuki-Miyaura, Mizoroki-Heck, and Nozaki-Hiyama-Kishi couplings. This compound facilitates the stereoselective synthesis of complex organic molecules, including biologically active compounds and materials.
- IUPAC
- 2-Ethenyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolane,2-Vinyl-4,4,5,5-tetramethyl-1,3,2-dioxaoborolane,4,4,5,5-Tetramethyl-2-vinyl-1,3,2-dioxaborolane
- Synonyms
- 2-Ethenyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolane2-Vinyl-4,4,5,5-tetramethyl-1,3,2-dioxaoborolane4,4,5,5-Tetramethyl-2-vinyl-1,3,2-dioxaborolane
Suzuki-Miyaura Coupling Reactions
Vinylboronic acid pinacol ester serves as a crucial coupling partner in Suzuki-Miyaura reactions, enabling the formation of carbon-carbon bonds for constructing diverse organic structures.
Mizoroki-Heck Reactions
This reagent can participate in Mizoroki-Heck reactions, particularly in cascade processes, to introduce vinyl groups into organic molecules and facilitate alkene synthesis.
Stereoselective Synthesis
It is utilized in stereoselective transformations, including intramolecular Nozaki-Hiyama-Kishi reactions and Cu-catalyzed couplings, to achieve precise control over molecular stereochemistry.
Preparation of Biologically Active Compounds
Vinylboronic acid pinacol ester is instrumental in the synthesis of various biologically significant molecules, such as enzymatic inhibitors, antibiotics, and receptor analogs.
| Molecular weight | 154.01 |
|---|---|
| Empirical formula | C8H15BO2 |
| Assay | 95% |
| Density | 0.908 g/mL at 25 °C(lit.) |
| Refractive index | n20/D 1.4300(lit.) |
| Storage temperature | −20°C |
| Contains / stabiliser | phenothiazine as stabilizer |
| Application | Reagent used for• Suzuki-Miyaura coupling reactions1• Mizoroki-Heck reactions (cascade reaction)1• Intramolecular Nozaki-Hiyama-Kishi reactions2• Stereoselective Cu-catalyzed γ-selective and stereospecific coupling3• Control of stereoselectivity and mechanistic portrait on intramolecular (4+1)-cycloaddition of dialkoxycarbenes4• Regio- and stereoselective synthesis of trisubstituted alkenes via gold(I)-catalyzed hydrophosphoryloxylation of haloalkynes followed by Pd-catalyzed consecutive cross-coupling reactions5• Asymmetric Birch reductive alkylation6Reagent used in Preparation of • Molecular tubes for lipid sensing7• Enzymatic inhibitors, antibiotics, receptor analogs, and other biologically significant compounds (including total syntheses)8,</sup |
Hazard statements
- H226Flammable liquid and vapour
- H317May cause an allergic skin reaction
Precautionary statements
- P280Wear protective gloves, clothing and eye/face protection
| Protective equipment | Eyeshields, Faceshields, full-face respirator (US), Gloves, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter |
|---|---|
| Flash point | 34 °C / 93.2 °F |
| Transport (UN / ADR) | UN 3272 3 / PGIII |
| Water hazard class (WGK, DE) | 3 |
| Hazard codes (EU) | Xi |
| Risk statements (R) | 10-43 |
| Safety statements (S) | 36/37 |
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 Vinylboronic acid pinacol ester used for?
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Vinylboronic acid pinacol ester is primarily used as a reagent in organic synthesis, particularly for Suzuki-Miyaura coupling reactions, Mizoroki-Heck reactions, and the stereoselective synthesis of complex molecules including biologically active compounds.
What is the CAS number and formula for Vinylboronic acid pinacol ester?
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The CAS number is 75927-49-0, and the empirical formula (Hill notation) is C8H15BO2.
What grade and purity does Tech Serve Solutions supply?
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Tech Serve Solutions supplies Vinylboronic acid pinacol ester with an assay of 95%. This product is not represented as USP, BP, EP, or any other pharmacopoeia grade.
What are the safety and handling precautions for Vinylboronic acid pinacol ester?
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Vinylboronic acid pinacol ester is a flammable liquid and may cause an allergic skin reaction. Handle with appropriate personal protective equipment, including eyeshields, gloves, and respiratory protection, in a well-ventilated area. Store at -20°C.
How are Vinylboronic acid pinacol ester products packed and shipped?
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Products are packed and shipped according to international regulations for hazardous materials. For Vinylboronic acid pinacol ester, it is classified as UN 3272, Hazard Class 3, Packing Group III.
How can I request a quote or sample of Vinylboronic acid pinacol ester?
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To request a quote or sample, please contact our sales department via the website or directly through our provided contact information, specifying the product CAS number 75927-49-0.
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