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Allylboronic acid pinacol ester, 98+%

Catalog No. aal1623203
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Catalog No. AAL1623203 Supplier Thermo Scientific Chemicals Supplier No. L1623203
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Description

CAS: 72824-04-5 | C9H17BO2 | 168.04 g/mol

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.

Chemical Identifiers

CAS 72824-04-5
Molecular Formula C9H17BO2
Molecular Weight (g/mol) 168.04
MDL Number MFCD00013347
InChI Key YMHIEPNFCBNQQU-UHFFFAOYSA-N
Synonym allylboronic acid pinacol ester, 2-allyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolane, allylboronic acid, pinacol cyclic ester, 4,4,5,5-tetramethyl-2-prop-2-en-1-yl-1,3,2-dioxaborolane, allylboronic acid piracol ester, 1,3,2-dioxaborolane, 4,4,5,5-tetramethyl-2-2-propenyl, 2-prop-2-en-1-yl-4,4,5,5-tetramethyl-1,3,2-dioxaborolane, allylboronicacidpinacolester, pinacol allylboronate, abape
PubChem CID 2763171
SMILES CC1(C)OB(CC=C)OC1(C)C

Specifications

Density 0.89
Boiling Point 50°C to 53°C (5 mmHg)
Flash Point 46°C (140°F)
Refractive Index 1.427
Quantity 1 g
UN Number UN3272
Beilstein 4244068
Solubility Information Not miscible or difficult to mix in water.
IUPAC Name 4,4,5,5-tetramethyl-2-prop-2-enyl-1,3,2-dioxaborolane
Formula Weight 168.05
Percent Purity ≥98%
Chemical Name or Material Allylboronic acid pinacol ester
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Safety and Handling

Hazard Category H226-H315-H319-H335
Hazard Statement GHS H Statement
H226
Flammable liquid and vapor.
Precautionary Statement P210-P233-P235-P240-P241-P242-P243-P261-P264b-P271-P280-P303+P361+P353-P304+P340-P305+P351+P338-P312-P332+P313-P363-P370+P378q-P501c
DOTInformation Transport Hazard Class: 3; Packing Group: III; Proper Shipping Name: ESTERS, N.O.S.
TSCA No
Recommended Storage Ambient temperatures

RUO – Research Use Only