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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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$41.13
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$252.65

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1 G
$41.13
10 G
$252.65

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

$41.13

List Price$51.60Save 20%
Web-Only Promotion

Available to ship onApril 29, 2025Details

Request a Bulk Order

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. [1]

Application

Reagent used for
  • Palladium-catalyzed Suzuki-Miyaura cross-coupling reactions and olefin metathesis[2]
  • Intermolecular radical additions[3]
  • Allylboration of aldehydes catalyzed by chiral spirobiindane diol (SPINOL) based phosphoric acids[4]
  • Cobalt-catalyzed regioselective hydrovinylation of dienes with alkenes[5]
  • Nucleic acid-templated energy transfer leading to a photorelease reaction[6]
  • Stereoselective indium-catalyzed Hosomi-Sakurai reactions[7]

Reagent used in Preparation of
  • Cyclic sulfone hydroxyethylamines as BACE1 inhibitors for reduction of Amyloid β-Peptides[8]
  • Transmetalation of carbene Ru iodide with Ag carboxylates to give C-H-activated Ru carbene complexes as catalysts for Z-selective olefin metathesis[9]
  • Allylboronation reagent for the preparation of allylic alcohols[10], and homoallylic amines.[11]

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

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Certificates of Analysis (COA)

Lot/Batch Number
SHBJ7207
SHBJ0632
SHBH5056V
SHBG7658V
SHBC9092V

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Asymmetric Allylboration of Aldehydes with Pinacol Allylboronates Catalyzed by 1,1'-Spirobiindane-7,7'-diol (SPINOL) Based Phosphoric Acids
Xing, C-H.; et al.
European Journal of Organic Chemistry, 6, 1115-1118 (2012)
Organometallics, 2, 230-230 (1983)
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)
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
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
View All Related Papers

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  1. How is shipping temperature determined? And how is it related to the product storage temperature?

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    1. Products may be shipped at a different temperature than the recommended long-term storage temperature. If the product quality is sensitive to short-term exposure to conditions other than the recommended long-term storage, it will be shipped on wet or dry-ice. If the product quality is NOT affected by short-term exposure to conditions other than the recommended long-term storage, it will be shipped at ambient temperature. As shipping routes are configured for minimum transit times, shipping at ambient temperature helps control shipping costs for our customers. For more information, please refer to the Storage and Transport Conditions document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/316/622/storage-transport-conditions-mk.pdf

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  2. How can I determine the shelf life / expiration / retest date of this product?

    1 answer

    1. If this product has an expiration or retest date, it will be shown on the Certificate of Analysis (COA, CofA). If there is no retest or expiration date listed on the product's COA, we do not have suitable stability data to determine a shelf life. For these products, the only date on the COA will be the release date; a retest, expiration, or use-by-date will not be displayed.
      For all products, we recommend handling per defined conditions as printed in our product literature and website product descriptions. We recommend that products should be routinely inspected by customers to ensure they perform as expected.
      For products without retest or expiration dates, our standard warranty of 1 year from the date of shipment is applicable.
      For more information, please refer to the Product Dating Information document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/449/386/product-dating-information-mk.pdf

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