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Allylboronic acid pinacol ester, 98+%
CAS: 72824-04-5 | C9H17BO2 | 168.04 g/mol
$82.08 - $273.62
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 |
| Catalog Number | Mfr. No. | Quantity | Price | Quantity | |||||
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| Catalog Number | Mfr. No. | Quantity | Price | Quantity | |||||
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AAL1623203
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Thermo Scientific Chemicals
L1623203 |
1 g |
Each for $82.08
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AAL1623206
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Thermo Scientific Chemicals
L1623206 |
5 g |
Each for $273.62
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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.
ApplicationsAllylboronic 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
| 72824-04-5 | |
| 168.04 | |
| YMHIEPNFCBNQQU-UHFFFAOYSA-N | |
| 2763171 |
| C9H17BO2 | |
| MFCD00013347 | |
| 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 | |
| CC1(C)OB(CC=C)OC1(C)C |
Specifications
| 72824-04-5 | |
| 50°C to 53°C (5 mmHg) | |
| C9H17BO2 | |
| MFCD00013347 | |
| UN3272 | |
| 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 | |
| YMHIEPNFCBNQQU-UHFFFAOYSA-N | |
| 4,4,5,5-tetramethyl-2-prop-2-enyl-1,3,2-dioxaborolane | |
| 2763171 | |
| ≥98% |
| 0.89 | |
| 46°C (140°F) | |
| 1.427 | |
| 1 g | |
| 4244068 | |
| Not miscible or difficult to mix in water. | |
| CC1(C)OB(CC=C)OC1(C)C | |
| 168.04 | |
| 168.05 | |
| Allylboronic acid pinacol ester |
Safety and Handling
GHS H Statement
H226
Flammable liquid and vapor.
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
H226-H315-H319-H335
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