Thermo Scientific Chemicals

Allylboronic acid pinacol ester, 98+%, Thermo Scientific Chemicals

Catalog number: L16232.03
1 g, Each
Thermo Scientific Chemicals

Allylboronic acid pinacol ester, 98+%, Thermo Scientific Chemicals

Catalog number: L16232.03
1 g, Each
Quantity
Catalog number: L16232.03
also known as L16232-03
Price (USD)
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Chemical Identifiers

CAS
72824-04-5
IUPAC Name
4,4,5,5-tetramethyl-2-(prop-2-en-1-yl)-1,3,2-dioxaborolane
Molecular Formula
C9H17BO2
InChI Key
YMHIEPNFCBNQQU-UHFFFAOYSA-N
SMILES
CC1(C)OB(CC=C)OC1(C)C
Assay (GC)
≥98.0%
Refractive Index
1.4245-1.4290 @ 20?C
Appearance (Color)
Clear colorless
Form
Liquid

Description

Allylboronic acid pinacol ester reacts with carboxylic acids, in the presence of tri-n-butyltin hydride, to give homoallylic alcohols in good yield. Homoallylic alcohols can also be formed by allylboration of aldehydes. It is a reagent used for palladium-catalyzed Suzuki-Miyaura cross-coupling reactions and olefin metathesis, intermolecular radical additions, allylboration of aldehydes catalyzed by chiral spirobiindane diol (SPINOL) based phosphoric acids, cobalt-catalyzed regioselective hydrovinylation of dienes with alkenes, nucleic acid-templated energy transfer leading to a photorelease reaction and stereoselective indium-catalyzed Hosomi-Sakurai reactions.

This Thermo Scientific Chemicals brand product was originally part of the Alfa Aesar product portfolio. Some documentation and label information may refer to the legacy brand. The original Alfa Aesar product / item code or SKU reference has not changed as a part of the brand transition to Thermo Scientific Chemicals.

Applications
Allylboronic acid pinacol ester reacts with carboxylic acids, in the presence of tri-n-butyltin hydride, to give homoallylic alcohols in good yield. Homoallylic alcohols can also be formed by allylboration of aldehydes. It is a reagent used for palladium-catalyzed Suzuki-Miyaura cross-coupling reactions and olefin metathesis, intermolecular radical additions, allylboration of aldehydes catalyzed by chiral spirobiindane diol (SPINOL) based phosphoric acids, cobalt-catalyzed regioselective hydrovinylation of dienes with alkenes, nucleic acid-templated energy transfer leading to a photorelease reaction and stereoselective indium-catalyzed Hosomi-Sakurai reactions.

Solubility
Not miscible or difficult to mix in water.

Notes
Store in cool place. Keep container tightly closed in a dry and well-ventilated place. Containers which are opened must be carefully resealed and kept upright to prevent leakage. Recommended storage temperature is 2 - 8°C. Store under inert gas. It is sensitive to moisture. Incompatible with oxidizing agents.
RUO – Research Use Only

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