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72824-04-5 Usage

Chemical Properties

Clear corless liquid

Uses

Different sources of media describe the Uses of 72824-04-5 differently. You can refer to the following data:
1. Allylboronic acid pinacol ester can act as 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 and Cobalt-catalyzed regioselective hydrovinylation of dienes with alkenes ; Nucleic acid-templated energy transfer leading to a photorelease reaction .
2. 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.

Check Digit Verification of cas no

The CAS Registry Mumber 72824-04-5 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 7,2,8,2 and 4 respectively; the second part has 2 digits, 0 and 4 respectively.
Calculate Digit Verification of CAS Registry Number 72824-04:
(7*7)+(6*2)+(5*8)+(4*2)+(3*4)+(2*0)+(1*4)=125
125 % 10 = 5
So 72824-04-5 is a valid CAS Registry Number.
InChI:InChI=1/C8H15BO2/c1-6-9-10-7(2,3)8(4,5)11-9/h6H,1H2,2-5H3

72824-04-5 Well-known Company Product Price

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  • TCI America

  • (A2157)  2-Allyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (stabilized with Phenothiazine)  >96.0%(GC)

  • 72824-04-5

  • 1g

  • 390.00CNY

  • Detail
  • TCI America

  • (A2157)  2-Allyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (stabilized with Phenothiazine)  >96.0%(GC)

  • 72824-04-5

  • 5g

  • 1,450.00CNY

  • Detail
  • Alfa Aesar

  • (L16232)  Allylboronic acid pinacol ester, 98+%   

  • 72824-04-5

  • 1g

  • 278.0CNY

  • Detail
  • Alfa Aesar

  • (L16232)  Allylboronic acid pinacol ester, 98+%   

  • 72824-04-5

  • 5g

  • 836.0CNY

  • Detail
  • Aldrich

  • (324647)  Allylboronicacidpinacolester  97%

  • 72824-04-5

  • 324647-1G

  • 353.34CNY

  • Detail
  • Aldrich

  • (324647)  Allylboronicacidpinacolester  97%

  • 72824-04-5

  • 324647-10G

  • 1,813.50CNY

  • Detail

72824-04-5SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 16, 2017

Revision Date: Aug 16, 2017

1.Identification

1.1 GHS Product identifier

Product name Allylboronic acid pinacol ester

1.2 Other means of identification

Product number -
Other names 4,4,5,5-tetramethyl-2-prop-2-enyl-1,3,2-dioxaborolane

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:72824-04-5 SDS

72824-04-5Relevant articles and documents

Umpolung of B?H Bonds by Metal–Ligand Cooperation with Cyclopentadienone Iridium Complexes

Higashi, Takuya,Kusumoto, Shuhei,Nozaki, Kyoko

supporting information, p. 2844 - 2848 (2020/12/18)

In contrast to conventional metal–ligand cooperative cleavage of a B?H bond, which provides a B cation on the ligand and an H anion on the metal, we report herein the umpolung of B?H bonds by novel cyclopentadienone iridium complexes. The B?H bonds of 4,4,5,5-tetramethyl-1,3,2-dioxaborolane (HBpin) and 1,8-naphthalenediaminatoborane (HBdan) were cleaved to give a B anion on the metal and an H cation on the phenolic oxygen atom of the ligand. Mechanistic investigation by DFT calculations revealed that the alkoxycarbonyl-substituted cyclopentadienone ligand facilitated deprotonation from Ir?H after oxidative addition of the B?H bond to give the umpolung product. The generated boryliridium complex was found to undergo borylation of an allyl halide in the presence of base, thus showing the nucleophilic nature of the boron atom.

Mechanism-based enhancement of scope and enantioselectivity for reactions involving a copper-substituted stereogenic carbon centre

Lee, Jaehee,Radomkit, Suttipol,Torker, Sebastian,Pozo, Juandel,Hoveyda, Amir H.

, p. 99 - 108 (2017/12/27)

A rapidly emerging set of catalytic reactions involves intermediates that contain a copper-substituted stereogenic carbon centre. Here, we demonstrate that an intimate understanding of this distinction provides ways for addressing limitations in reaction scope and explaining why unexpected variations in enantioselectivity often occur. By using catalytic enantioselective Cu-boryl addition to alkenes as the model process, we elucidate several key mechanistic principles. We show that higher electrophile concentration can lead to elevated enantioselectivity. This is because diastereoselective Cu-H elimination may be avoided and/or achiral Cu-boryl intermediates can be converted to allyl-B(pin) rather than add to an alkene. We illustrate that lower alkene amounts and/or higher chiral ligand concentration can minimize the deleterious influence of achiral Cu-alkyl species, resulting in improved enantiomeric ratios. Moreover, and surprisingly, we find that enantioselectivities are higher with the less reactive allylphenyl carbonates as chemoselective copper-hydride elimination is faster with an achiral Cu-alkyl species.

Enantioselective syn and anti homocrotylation of aldehydes: Application to the formal synthesis of spongidepsin

Lin, Hongkun,Tian, Leiming,Krauss, Isaac J.

supporting information, p. 13176 - 13182 (2015/10/28)

Whereas crotylboration has been a useful method for synthesis of stereochemically complex products, we have shown that homocrotylboration can be achieved with cyclopropanated crotylation reagents, and that the stereoselectivity of the reaction can be predicted by analogous models. This paper presents a full account of this work, including the first examples of asymmetric anti homocrotylation. The scope of this reaction is demonstrated with highly enantioselective homocrotylation of both aliphatic and aromatic aldehydes, as well as double diastereoselection studies. An application of the synthesis of the marine natural product spongidepsin is presented, as well as streamlined syntheses of homocrotylation reagents.

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