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633348

Sigma-Aldrich

Vinylboronsäurepinakolester

contains phenothiazine as stabilizer, 95%

Synonym(e):

4,4,5,5-Tetramethyl-2-vinyl-1,3,2-dioxaborolan

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About This Item

Empirische Formel (Hill-System):
C8H15BO2
CAS-Nummer:
75927-49-0
Molekulargewicht:
154.01
MDL-Nummer:
MFCD00192492
UNSPSC-Code:
12352103
PubChem Substanz-ID:
24882546
NACRES:
NA.22

Assay

95%

Enthält

phenothiazine as stabilizer

Brechungsindex

n20/D 1.4300 (lit.)

Dichte

0.908 g/mL at 25 °C (lit.)

Lagertemp.

−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

InChIKey

DPGSPRJLAZGUBQ-UHFFFAOYSA-N

Anwendung

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)

Signalwort

Warning

Gefahreneinstufungen

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

Lagerklassenschlüssel

3 - Flammable liquids

WGK

WGK 3

Flammpunkt (°F)

93.2 °F

Flammpunkt (°C)

34 °C

Persönliche Schutzausrüstung

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

Hier finden Sie alle aktuellen Versionen:

Analysenzertifikate (COA)

Lot/Batch Number
MKCP9314
SHBJ8428
SHBH3774V
SHBG8693V
SHBD6089V

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4-Vinylphenylborsäure ≥95%

Sigma-Aldrich

417580

4-Vinylphenylborsäure

Tributyl(vinyl)zinn 97%

Sigma-Aldrich

271438

Tributyl(vinyl)zinn

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.
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
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
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.
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