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Sigma-Aldrich

Allylboronic acid pinacol ester

97%

Synonym(s):

2-Allyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolane, 4,4,5,5-tetramethyl-2-(2-propen-1-yl)-1,3,2-dioxaborolane, 4,4,5,5-tetramethyl-2-(2-propenyl)-1,3,2-dioxaborolane, Allyl pinacol boronate, Pinacol allylboronate, Pinacolyl 2-propenylboronate

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About This Item

Linear Formula:
((CH3)4C2O2)BCH2CH=CH2
CAS Number:
72824-04-5
Molecular Weight:
168.04
MDL number:
MFCD00013347
UNSPSC Code:
12352103
PubChem Substance ID:
24859457
NACRES:
NA.22

Quality Level

100

assay

97%

refractive index

n20/D 1.4268 (lit.)

bp

50-53 °C/5 mmHg (lit.)

density

0.896 g/mL at 25 °C (lit.)

storage temp.

2-8°C

SMILES string

CC1(C)OB(CC=C)OC1(C)C

InChI

1S/C9H17BO2/c1-6-7-10-11-8(2,3)9(4,5)12-10/h6H,1,7H2,2-5H3

InChI key

YMHIEPNFCBNQQU-UHFFFAOYSA-N

Related Categories

General description

Allylboronic acid pinacol ester is used as a nucleophile in the catalytic allylation of simple ketoimines.

Application

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
  • Stereoselective indium-catalyzed Hosomi-Sakurai reactions

Reagent used in Preparation of
  • Cyclic sulfone hydroxyethylamines as BACE1 inhibitors for reduction of Amyloid β-Peptides
  • Transmetalation of carbene Ru iodide with Ag carboxylates to give C-H-activated Ru carbene complexes as catalysts for Z-selective olefin metathesis
  • Allylboronation reagent for the preparation of allylic alcohols, and homoallylic amines.

pictograms

Flame
GHS02

signalword

Warning

hcodes

H226

Hazard Classifications

Flam. Liq. 3

Storage Class

3 - Flammable liquids

wgk_germany

WGK 3

flash_point_f

114.8 °F - closed cup

flash_point_c

46 °C - closed cup

ppe

Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter

Certificates of Analysis (COA)

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Manuel Röthlingshöfer et al.
Journal of the American Chemical Society, 133(45), 18110-18113 (2011-10-19)
The photocleavage of a nitrobenzyl-type linker (NPPOC) at 405 nm wavelength was enabled by nucleic acid-templated energy transfer from a sensitizer (thioxanthenone) to the linker. This strategy was used to release profluorescent rhodamine, which facilitated monitoring of the reaction via
A catalytic asymmetric borono variant of Hosomi-Sakurai reactions with N,O-aminals.
Yi-Yong Huang et al.
Angewandte Chemie (International ed. in English), 50(47), 11121-11124 (2011-10-07)
Heinrich Rueeger et al.
Journal of medicinal chemistry, 55(7), 3364-3386 (2012-03-03)
Structure-based design of a series of cyclic hydroxyethylamine BACE1 inhibitors allowed the rational incorporation of prime- and nonprime-side fragments to a central core template without any amide functionality. The core scaffold selection and the structure-activity relationship development were supported by
Marion Arndt et al.
Organic letters, 13(23), 6236-6239 (2011-11-02)
The absolute control of the regiochemistry of a cobalt-catalyzed 1,4-hydrovinylation reaction is achieved by alternation of the ligands applied. While the dppe/dppp ligands led to the formation of the branched product, the herein described application of the SchmalzPhos ligand generates
Organometallics, 2, 230-230 (1983)
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Boronic Acid Esters

The synthesis of biaryl compounds via the Suzuki–Miyaura coupling reaction has become more commonplace now that many arylboronic acids are readily available.

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