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663212

Sigma-Aldrich

Isopropenylboronic acid pinacol ester

contains phenothiazine as stabilizer, 95%

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
MDL number:
MFCD08276843
UNSPSC Code:
12352103
PubChem Substance ID:
24884621
NACRES:
NA.22

Assay

95%

contains

phenothiazine 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

SMILES string

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

InChI

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

InChI key

SVSUYEJKNSMKKW-UHFFFAOYSA-N

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

Signal Word

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 Code

3 - Flammable liquids

WGK

WGK 3

Flash Point(F)

107.6 °F

Flash Point(C)

42 °C

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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Catalytic asymmetric intramolecular hydroacylation with rhodium/phosphoramidite-alkene ligand complexes.
Thomas J Hoffman et al.
Angewandte Chemie (International ed. in English), 50(45), 10670-10674 (2011-09-20)
Facile Access to 3,5-Dihalogenated Pyrazoles by Sydnone Cycloaddition and their Versatile Functionalization by Pd-Catalyzed Cross-Coupling Processes
Delaunay, T.; et al.
European Journal of Organic Chemistry, 20-21, 3837-3848 (2011)
Halosulfonylation of unsaturated boronic esters: access to new electron-deficient alkenes and dienes
Guennouni, N.; et al.
Synlett, 7, 581-584 (1992)
Simmons-Smith cyclopropanation reaction
Charette, A. B.; Beauchemin, A.
Org. React., 58 (2001)
First Total Synthesis of Rhodexin A
Jung, M. E.; Yoo, D.
Organic Letters, 13, 3766-3766 (2011)
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