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633348

Sigma-Aldrich

Vinylboronic acid pinacol ester

contains phenothiazine as stabilizer, 95%

Synonyme(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

Formule empirique (notation de Hill):
C8H15BO2
Numéro CAS:
75927-49-0
Poids moléculaire :
154.01
Numéro MDL:
MFCD00192492
Code UNSPSC :
12352103
ID de substance PubChem :
24882546
Nomenclature NACRES :
NA.22

Niveau de qualité

100

Pureté

95%

Contient

phenothiazine as stabilizer

Indice de réfraction

n20/D 1.4300 (lit.)

Densité

0.908 g/mL at 25 °C (lit.)

Température de stockage

−20°C

Chaîne SMILES 

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

Clé InChI

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)

Pictogrammes

FlameExclamation markEnvironment
GHS02,GHS07,GHS09

Mention d'avertissement

Warning

Mentions de danger

H226,H317,H411

Classification des risques

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

Code de la classe de stockage

3 - Flammable liquids

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

93.2 °F

Point d'éclair (°C)

34 °C

Équipement de protection individuelle

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

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Certificats d'analyse (COA)

Lot/Batch Number
MKCW2120
0000202873
0000201611
MKCP9314
SHBJ8428

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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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Organic & biomolecular chemistry, 9(23), 8112-8118 (2011-10-26)
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The Journal of organic chemistry, 77(2), 851-857 (2012-01-24)
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