Isopropenylboronic acid pinacol ester

Isopropenylboronic acid pinacol ester Basic information
Description Sources
Product Name:Isopropenylboronic acid pinacol ester
Synonyms:2-(1-Methylethenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane;2-Isopropenyl boronic acid pinacol ester;Isopropenylboronic acid pinacol ester;4,4,5,5-tetramethyl-2-(1-methylethenyl)-1,3,2-dioxaborolane;4,4,5,5-Tetramethyl-2-(isopropenyl)-1,3,2-dioxaborolane;2-Isopropenyl-4,4,5,5-tetraMethyl-1,3,2-dioxaborolane(Isopropenylboronic acid pinacol ester);2-Isopropenyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolane, 2-(Prop-1-en-2-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane;1,3,2-Dioxaborolane,4,4,5,5-tetraMethyl-2-(1-Methylethenyl)-
CAS:126726-62-3
MF:C9H17BO2
MW:168.04
EINECS:
Product Categories:Alkenyl Boronate Esters;Boronate Esters;Boronic Acids and Derivatives;Chemical Synthesis;Organometallic Reagents;Alkyl;Organoborons
Mol File:126726-62-3.mol
Isopropenylboronic acid pinacol ester Structure
Isopropenylboronic acid pinacol ester Chemical Properties
Melting point 157-161 °C
Boiling point 47-49 °C/9 mbar
density 0.894 g/mL at 25 °C
refractive index 1.4320
Fp 42 °C
storage temp. 2-8°C
solubility Chloroform (Slightly), Ethyl Acetate (Slightly)
form Liquid
color Clear, colorless to brown
InChIKeySVSUYEJKNSMKKW-UHFFFAOYSA-N
CAS DataBase Reference126726-62-3
Safety Information
Hazard Codes Xi
Risk Statements 10-36/37/38-43
Safety Statements 16-26-36/37
RIDADR UN 1993
WGK Germany 3
TSCA No
HazardClass IRRITANT
PackingGroup 
HS Code 29349990
MSDS Information
Isopropenylboronic acid pinacol ester Usage And Synthesis
DescriptionIsopropenylboronic acid pinacol ester is a versatile ester 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 and preparation of various therapeutic kinase and enzymatic inhibitors1. It can be used as an intermediate in the synthesis of variety of cyclic and acyclic organic compounds. It is also shown that the α-Substituted Allyl/Croty of this compound can be used for highly Diastereoand Enantioselective allylboration of aldehydes2.
Sources
  1. https://www.sigmaaldrich.com/catalog/product/aldrich/663212?lang=en&region=US
  2. https://www.trc-canada.com/product-detail/?I821825
Usessuzuki reaction
UsesIsopropenylboronic Acid Pinacol Ester, can be used as an intermediate in the synthesis of variety of cyclic and acyclic organic compounds. It is also shown that the α-Substituted Allyl/Croty of this compound can be used for highly Diastereo- and Enantioselective allylboration of aldehydes.
UsesReagent 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
Potassium isopropenyltrifluoroborate ETHYL 4-AMINO-5-IMIDAZOLECARBOXYLATE ETHYL4-[2-(1,3-DIOXO-1,3-DIHYDRO-2H-ISOINDOL-2-YL)ETHOXYL]-3-OXOBUTANOATE Ethyl-2-(diphenylaMino)pyriMidine-5-carboxylate Isopropenylboronic acid pinacol ester POLY(N-ISOPROPYL ACRYLAMIDE) CIS-1,2-BIS(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)STILBENE 1-VINYL-(CIS-1,2-BIS(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL))CYCLOHEXAN-1-OL 1-PHENYLVINYLBORONIC ACID PINACOL ESTER 1,4-DIOXA-SPIRO[4,5]DEC-7-EN-8-BORONIC ACID, PINACOL ESTER 1-CIS-1,2-BIS(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)PENTENE METHYL 4 4 5 5-TETRAMETHYL-ALPHA-(1-(4 4,4-DIMETHYLCYCLOHEXA-1,5-DIENYLBORONIC ACID PINACOL ESTER 1,3-DIMETHYLURACIL-5-BORONIC ACID PINACOL ESTER BUTYL OLEATE CIS-1,2-BIS(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)STILBENE 1-CIS-1,2-BIS(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)HEPTENE 1-(4-FLUOROPHENYL)VINYLBORONIC ACID, PINACOL ESTER

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