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633348

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
NACRES:
NA.22
PubChem Substance ID:
24882546
UNSPSC Code:
12352103
MDL number:
MFCD00192492
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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

Application

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)
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.

Disclaimer

Supply conditions do not apply to the regions and states of Brazil: North, Northeast, Mato Grosso do Sul, Mato Grosso, and Rio Grande do Sul.

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Warning

Hazard Classifications

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

Storage Class

3 - Flammable liquids

wgk

WGK 3

flash_point_f

93.2 °F

flash_point_c

34 °C

ppe

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

Regulatory Information

危险化学品

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Certificates of Analysis (COA)

Lot/Batch Number
0000516720
0000516721
0000516720
0000516721
MKCZ4100

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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)
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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Global Trade Item Number

SKUGTIN
633348-1G04061837894411
633348-10G04061832721590