633348

Vinylboronic acid pinacol ester

contains phenothiazine as stabilizer, 95%

• Synonym(s): 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
• Empirical Formula (Hill Notation): C₈H₁₅BO₂
• CAS Number: 75927-49-0
• Molecular Weight: 154.01
• MDL number: MFCD00192492
• UNSPSC Code: 12352103
• PubChem Substance ID: 24882546
• NACRES: NA.22

Properties

• Assay: 95%
• contains: phenothiazine as stabilizer
• refractive index: n20/D 1.4300 (lit.)
• density: 0.908 g/mL at 25 °C (lit.)
• storage temp.: −20°C
• SMILES string: CC1(C)OB(OC1(C)C)C=C
• InChI: 1S/C8H15BO2/c1-6-9-10-7(2,3)8(4,5)11-9/h6H,1H2,2-5H3
• InChI key: DPGSPRJLAZGUBQ-UHFFFAOYSA-N

Description

Application

Employed in a "double" Heck-Mizoroki arylation leading to β,β-diarylated vinyl boronates which react with an additional aryl halide to form Π-extended systems. This approach was used to prepare conjugated dendrimers. Also used to prepare γ-carbonyl vinyl boronates via a light-induced radical addition of xanthates.

Reagent used for

• Suzuki-Miyaura coupling reactions
• Mizoroki-Heck reactions (cascade reaction)
• Intramolecular Nozaki-Hiyama-Kishi reactions
• Stereoselective Cu-catalyzed γ-selective and stereospecific coupling
• Control of stereoselectivity and mechanistic portrait on intramolecular (4+1)-cycloaddition of dialkoxycarbenes
• Regio- and stereoselective synthesis of trisubstituted alkenes via gold(I)-catalyzed hydrophosphoryloxylation of haloalkynes followed by Pd-catalyzed consecutive cross-coupling reactions
• Asymmetric Birch reductive alkylation

Reagent used in Preparation of

• Molecular tubes for lipid sensing
• Enzymatic inhibitors, antibiotics, receptor analogs, and other biologically significant compounds (including total syntheses)

Safety Information

• Pictograms: GHS02,GHS07,GHS09
• Signal Word: Warning
• Hazard Statements: H226,H317,H411
• Precautionary Statements: P210 - P233 - P240 - P273 - P280 - P303 + P361 + P353
• Hazard Classifications: Aquatic Chronic 2 - Flam. Liq. 3 - Skin Sens. 1
• Storage Class Code: 3 - Flammable liquids
• WGK: WGK 3
• Flash Point(F): 93.2 °F
• Flash Point(C): 34 °C
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves