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72824-04-5 - Allylboronic acid pinacol ester, 98+% - 2-Allyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolane - L16232 - Alfa Aesar

L16232 Allylboronic acid pinacol ester, 98+%

CAS Number
72824-04-5
Synonyms
2-Allyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

Size Price ($) Quantity Availability
1g 33.10
5g 116.00
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Allylboronic acid pinacol ester, 98+%

MDL
MFCD00013347

Chemical Properties

Formula
C9H17BO2
Formula Weight
168.05
Boiling Point
50-53°/5mm
Flash Point
46°(140°F)
Density
0.890
Refractive Index
1.4270
Solubility
Not miscible or difficult to mix in water.

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.

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.

Literature References

Sambasivarao Kotha.; Arjun S Chavan.; Mobin Shaikh. Diversity-oriented approach to macrocyclic cyclophane derivatives by Suzuki-Miyaura cross-coupling and olefin metathesis as key steps. Journal of Organic Chemistry. 2012, 77 (1), 482-489.

Nicolas Charrier, Zhibo Liu, Samir Z Zard. Desulfonylative radical ring closure onto aromatics. A modular route to benzazepin-2-ones and 5-arylpiperidin-2-ones. Organic Letters. 2012, 14 (8), 2018-2021.

Reacts with carboxylic acids, in the presence of tri-n-butyltin hydride, to give homoallylic alcohols in good yield: Synthesis, 1573 (2001):

Homoallylic alcohols can also be formed by allylboration of aldehydes; the reaction has been found to be accelerated by Lewis acids, e.g. AlCl3 or Sc(OTf)3: J. Am. Chem. Soc., 124, 12414 (2002).

GHS Hazard and Precautionary Statements

Hazard Statements: H226

Flammable liquid and vapour.

Precautionary Statements: P210-P280a-P240-P241-P303+P361+P353-P501a

Keep away from heat/sparks/open flames/hot surfaces. - No smoking. Wear protective gloves and eye/face protection. Ground/bond container and receiving equipment. Use explosion-proof electrical/ventilating/lighting/ equipment. IF ON SKIN (or hair): Remove/Take off immediately all contaminated clothing. Rinse skin with water/shower. Dispose of contents/container in accordance with local/regional/national/international regulations.

Other References

Beilstein
4244068
Hazard Class
3
Packing Group
III
Harmonized Tariff Code
2934.99
TSCA
No

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