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633348 Sigma-Aldrich

Vinylboronic acid pinacol ester

contains phenothiazine as stabilizer, 95%

Synonym: 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

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Properties

Related Categories Alkenyl Boronate Esters, Boronate Esters, Boronic Acids and Derivatives, Chemical Synthesis, Organometallic Reagents More...
InChI Key   DPGSPRJLAZGUBQ-UHFFFAOYSA-N
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

Description

Application

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)

Packaging

1, 10 g in glass bottle

Safety & Documentation

Safety Information

Symbol 
Signal word 
Warning
Hazard statements 
Precautionary statements 
RIDADR 
UN 3272 3 / PGIII
WGK Germany 
3
Flash Point(F) 
93.2 °F
Flash Point(C) 
34 °C
Protocols & Articles

Articles

Boronic Acid Esters - Chemfiles Volume 4 Article 2

The synthesis of biaryl compounds via the Suzuki–Miyaura coupling reaction has become more commonplace now that many arylboronic acids are readily available. Several years ago, Miyaura et al. demonst...
Chemfiles Volume 4 Article 2
Keywords: Coupling reactions, Suzuki-Miyaura coupling

Peer-Reviewed Papers
15

References

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