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633348

Sigma-Aldrich

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

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About This Item

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

Quality Level

100

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

Related Categories

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)

Signal Word

Warning

Hazard Statements

H226,H317,H411

Hazard Classifications

Aquatic Chronic 2 - Flam. Liq. 3 - Skin Sens. 1

WGK

WGK 3

Flash Point(F)

93.2 °F

Flash Point(C)

34 °C

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Information

危险化学品

Certificates of Analysis (COA)

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Leslie Duroure et al.
Organic & biomolecular chemistry, 9(23), 8112-8118 (2011-10-26)
Simple models of the spiroimine core of (-)-gymnodimine A have been synthesized in racemic and optically active forms. The quaternary carbon of the racemic spiroimines was created by Michael addition of a β-ketoester to acrolein, whereas the asymmetric allylic alkylation
Palladium-catalyzed convergent synthesis and properties of conjugated dendrimers based on triarylethene branching.
Kenichiro Itami et al.
Angewandte Chemie (International ed. in English), 45(15), 2404-2409 (2006-03-10)
Christopher T Avetta et al.
The Journal of organic chemistry, 77(2), 851-857 (2012-01-24)
Two fluorescent sensors for lipids have been prepared and tested for detection of a number of hydrophobic compounds of varying shape and size. The data suggest that the two sensors have a different mode of fluorescent response. Yet, the two
Beatriz Blanco et al.
Organic & biomolecular chemistry, 10(18), 3662-3676 (2012-03-27)
Several 3-alkylaryl mimics of the enol intermediate in the reaction catalyzed by type II dehydroquinase were synthesized to investigate the effect on the inhibition potency of replacing the oxygen atom in the side chain by a carbon atom. The length
Total Synthesis and Biological Evaluation of the Fab-Inhibitory Antibiotic Platencin and Analogues Thereof
Leung, G. Y.; et al.
European Journal of Organic Chemistry, 1, 183-196 (2011)
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