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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-Nummer
72824-04-5
Synonyme
2-Allyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

Größe Preis ($) Menge Verfügbarkeit
1g 33,48
5g 112,85
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Allylboronic acid pinacol ester, 98+%

MDL
MFCD00013347

Chemische Eigenschaften

Formel
C9H17BO2
Molmasse
168.05
Siedepunkt
50-53°/5mm
Flammpunkt
46°(140°F)
Dichte
0.890
Brechungsindex
1.4270
Löslichkeit
Not miscible or difficult to mix in water.

Anwendungen

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.

Bemerkungen

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.

Literaturverweise

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 Gefahren- und Sicherheitshinweise

Gefahrenhinweise (EU): H226

Flammable liquid and vapour.

Sicherheitshinweise: P210-P280-P240-P241-P233-P242-P243-P303+P361+P353-P403+P235-P501a

Keep away from heat/sparks/open flames/hot surfaces. - No smoking. Wear protective gloves/protective clothing/eye protection/face protection. Ground/bond container and receiving equipment. Use explosion-proof electrical/ventilating/lighting/ equipment. Keep container tightly closed. Use only non-sparking tools. Take precautionary measures against static discharge. IF ON SKIN (or hair): Remove/Take off immediately all contaminated clothing. Rinse skin with water/shower. Store in a well-ventilated place. Keep cool. Dispose of contents/container in accordance with local/regional/national/international regulations.

Weitere Referenzen

Beilstein
4244068
Gefahrenklasse
3
Verpackungsgruppe
III
Harmonized Tariff Code
2934.99
TSCA
No

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