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Sigma-Aldrich

Vinylboronic acid pinacol ester

contains phenothiazine as stabilizer, 95%

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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:
Molecular Weight:
154.01
MDL number:
PubChem Substance ID:
NACRES:
NA.22

Quality Level

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

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This Item
663212659851
refractive index

n20/D 1.4300 (lit.)

refractive index

n20/D 1.4320

refractive index

n20/D 1.433

density

0.908 g/mL at 25 °C (lit.)

density

0.894 g/mL at 25 °C

density

0.922 g/mL at 25 °C

storage temp.

−20°C

storage temp.

2-8°C

storage temp.

-

contains

phenothiazine as stabilizer

contains

phenothiazine as stabilizer

contains

-

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

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

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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.
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.
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.
Francis Beaumier et al.
Journal of the American Chemical Society, 134(13), 5938-5953 (2012-03-13)
The stereoselective synthesis of 5-5, 6-5, and 7-5 fused O-heterocyclic compounds is reported. The key reaction is a formal intramolecular (4 + 1)-cycloaddition involving a dialkoxycarbene and an electron-deficient diene where the stereoselectivity is dependent on the length of the
Mingyu Yang et al.
Organic letters, 14(3), 816-819 (2012-01-20)
A Cu-catalyzed γ-selective coupling reaction between propargylic phosphates and aryl- or alkenylboronates afforded aryl- or alkenyl-conjugated allenes. The reaction showed excellent functional group compatibility in both the propargylic substrates and the boronates. The reaction of an enantioenriched propargylic phosphate proceeded

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