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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

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

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)

signalword

Warning

Hazard Classifications

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

Storage Class

3 - Flammable liquids

wgk_germany

WGK 3

flash_point_f

93.2 °F

flash_point_c

34 °C

ppe

Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter

Certificates of Analysis (COA)

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Bathoju Chandra Chary et al.
Chemical communications (Cambridge, England), 47(27), 7851-7853 (2011-06-07)
A new stereoselective synthesis of trisubstituted alkenes is developed. Hydrophosphoryloxylation of haloalkynes provides Z-alkenyl halophosphates, which undergo Pd-catalyzed consecutive cross-coupling reactions to afford regio- and stereodefined trisubstituted alkenes.
Christopher A Leclair et al.
Tetrahedron letters, 51(52), 6852-6855 (2011-04-26)
A total synthesis of LL-Z1640-2 (2), a potent and selective kinase inhibitor, has been completed. The key step of the convergent synthesis utilized a late-stage intramolecular Nozaki-Hiyama-Kishi (NHK) reaction to close the macrocycle at the C6'-C7' bond.
Markus R Heinrich et al.
Chemical communications (Cambridge, England), (24), 3077-3079 (2005-06-17)
Gamma-carbonyl vinyl boronates can be prepared by a visible light induced radical chain addition of an S-acyl dithiocarbonate (xanthate) to the pinacol ester of vinyl boronic acid, followed by treatment with base.
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)
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
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