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Merck
CN

663212

Isopropenylboronic acid pinacol ester

contains BHT as stabilizer, 94.5%

Synonym(s):

2-Isopropenyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolane, 4,4,5,5-Tetramethyl-2-(isopropenyl)-1,3,2-dioxaborolane, 4,4,5,5-Tetramethyl-2-(prop-1-en-2-yl)-1,3,2-dioxaborolane, 4,4,5,5-tetramethyl-2-(1-methylethenyl)-1,3,2-dioxaborolane

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About This Item

Empirical Formula (Hill Notation):
C9H17BO2
CAS Number:
126726-62-3
Molecular Weight:
168.04
NACRES:
NA.22
PubChem Substance ID:
24884621
UNSPSC Code:
12352103
MDL number:
MFCD08276843

Key Documents

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InChI

1S/C9H17BO2/c1-7(2)10-11-8(3,4)9(5,6)12-10/h1H2,2-6H3

SMILES string

CC(=C)B1OC(C)(C)C(C)(C)O1

InChI key

SVSUYEJKNSMKKW-UHFFFAOYSA-N

assay

94.5%

contains

BHT as stabilizer

refractive index

n20/D 1.4320

bp

47-49 °C/9 mbar

density

0.894 g/mL at 25 °C

storage temp.

2-8°C

Quality Level

100

Related Categories

Application

Reagent used for
  • Palladium-catalyzed Suzuki-Miyaura cross-coupling processes
  • Inverse-electron-demand Diels-Alder reaction
  • Simmons-Smith Cyclopropanation Reaction
  • Polyene cyclization
  • Stereoselective aldol reactions
  • Grubbs cross-metathesis reaction
  • Intramolecular Suzuki-Miyaura reaction
  • Stereoselective cross-metathesis
  • Dipolar cycloaddition
  • Iodosulfonylation
  • Asymmetric conjugate addition and intramolecular hydroacylation

Reagent used in preparation of various therapeutic kinase and enzymatic inhibitors
Reagent used for
  • Palladium-catalyzed Suzuki-Miyaura cross-coupling reactions
  • Inverse-electron-demand Diels-Alder reaction
  • Simmons-Smith Cyclopropanation Reaction
  • Polyene cyclization
  • Stereoselective aldol reactions
  • Grubbs cross-metathesis reaction
  • Intramolecular Suzuki-Miyaura reaction
  • Stereoselective cross-metathesis
  • Dipolar cycloaddition
  • Iodosulfonylation
  • Asymmetric conjugate addition and intramolecular hydroacylation

Reagent used in preparation of various therapeutic kinase and enzymatic inhibitors

pictograms

FlameExclamation mark
GHS02,GHS07

signalword

Warning

Hazard Classifications

Aquatic Chronic 3 - Eye Irrit. 2 - Flam. Liq. 3 - Skin Irrit. 2 - Skin Sens. 1 - STOT SE 3

target_organs

Respiratory system

Storage Class

3 - Flammable liquids

wgk

WGK 3

flash_point_f

107.6 °F

flash_point_c

42 °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
MKCZ4160
MKCQ9407
MKCP4891
SHBJ7424
SHBH5064V

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Synthesis of tri-substituted vinyl boronates via ruthenium-catalyzed olefin cross-metathesis
Morrill, C.; Funk, T. W.; Grubbs, R. H.
Tetrahedron Letters, 45, 7733-7736 (2004)
Total synthesis of apoptolidinone.
Bin Wu et al.
Angewandte Chemie (International ed. in English), 43(48), 6673-6675 (2004-12-14)
Evaluation of thieno[3,2-b]pyrrole[3,2-d]pyridazinones as activators of the tumor cell specific M2 isoform of pyruvate kinase
Jiang, J-k.; et al.
Bioorganic & Medicinal Chemistry, 20, 3387-3393 (2010)
The 1,3-dipolar cycloaddition of nitrile oxides to vinylboronic esters
Wallace, R. H.; Zong, K. K.; Schoene, M. P.
Current Topics in the Chemistry of Boron, 143, 78-81 (1994)
Halosulfonylation of unsaturated boronic esters: access to new electron-deficient alkenes and dienes
Guennouni, N.; et al.
Synlett, 7, 581-584 (1992)
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