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Merck
CN

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

Key Documents

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InChI

1S/C8H15BO2/c1-6-9-10-7(2,3)8(4,5)11-9/h6H,1H2,2-5H3

SMILES string

CC1(C)OB(OC1(C)C)C=C

InChI key

DPGSPRJLAZGUBQ-UHFFFAOYSA-N

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

Quality Level

100

Related Categories

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

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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Christopher T Avetta et al.
The Journal of organic chemistry, 77(2), 851-857 (2012-01-24)
Two fluorescent sensors for lipids have been prepared and tested for detection of a number of hydrophobic compounds of varying shape and size. The data suggest that the two sensors have a different mode of fluorescent response. Yet, the two
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)
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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
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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