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663212 Sigma-Aldrich

Isopropenylboronic acid pinacol ester

contains phenothiazine as stabilizer, 95%

Synonym: 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

  • CAS Number 126726-62-3

  • Empirical Formula (Hill Notation) C9H17BO2

  • Molecular Weight 168.04

  •  MDL number MFCD08276843

  •  PubChem Substance ID 24884621

  •  NACRES NA.22

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Properties

Related Categories Alkenyl Boronate Esters, Boronate Esters, Boronic Acids and Derivatives, Chemical Synthesis, Organometallic Reagents More...
Quality Level   100
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

Description

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

9

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

Packaging

5, 25 g in glass bottle

Safety & Documentation

Safety Information

Symbol 
Signal word 
Warning
Hazard statements 
Target organs 
Respiratory system
RIDADR 
UN 1993C 3 / PGIII
WGK Germany 
WGK 3
Flash Point(F) 
107.6 °F
Flash Point(C) 
42 °C
Protocols & Articles

Articles

Boronic Acid Esters - Chemfiles Volume 4 Article 2

The synthesis of biaryl compounds via the Suzuki–Miyaura coupling reaction has become more commonplace now that many arylboronic acids are readily available. Several years ago, Miyaura et al. demonst...
Chemfiles Volume 4 Article 2
Keywords: Coupling reactions, Suzuki-Miyaura coupling

Suzuki Coupling | ChemFiles 2006, 6.2, 10.

C–C bond formation via the Suzuki–Miyaura reaction is one of the most powerful and thoroughly explored facets of Pdcatalyzed cross-coupling. The boron-based nucleophiles utilized in this reaction off...
ChemFiles 2006, 6.2, 10.
Keywords: Addition reactions, C-C bond formation, Coupling reactions, Cross couplings, Epoxidations, Halogenations, Ligands, Microwave synthesis, Ozonolysis, Suzuki coupling, Vinylations

Peer-Reviewed Papers
15

References

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