Skip to Content
Merck
All Photos(2)

Documents

710210

Sigma-Aldrich

(E)-3-(tert-Butyldimethylsilyloxy)propene-1-yl-boronic acid pinacol ester

97%

Synonym(s):

(E)-2-[3-[[(1,1-Dimethylethyl)dimethylsilyl]oxy]-1-propenyl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane, 2-[(1E)-3-[[(1,1-Dimethylethyl)dimethylsilyl]oxy]-1-propenyl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane, tert-Butyldimethyl[[(2E)-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)prop-2-en-1-yl]oxy]silane

Sign Into View Organizational & Contract Pricing
All Photos(2)

About This Item

Empirical Formula (Hill Notation):
C15H31BO3Si
CAS Number:
114653-19-9
Molecular Weight:
298.30
MDL number:
MFCD15144803
UNSPSC Code:
12352103
PubChem Substance ID:
329762909
NACRES:
NA.22

Assay

97%

form

liquid

density

0.910 g/mL at 25 °C

SMILES string

CC(C)(C)[Si](C)(C)OC\C=C\B1OC(C)(C)C(C)(C)O1

InChI

1S/C15H31BO3Si/c1-13(2,3)20(8,9)17-12-10-11-16-18-14(4,5)15(6,7)19-16/h10-11H,12H2,1-9H3/b11-10+

InChI key

LUURLZJMKOVITO-ZHACJKMWSA-N

Application

(E)-3-(tert-Butyldimethylsilyloxy)propene-1-yl-boronic acid pinacol ester can be used as a reactant in:
  • Palladium-catalyzed Suzuki-Miyaura coupling reaction.
  • The synthesis of anti-homoallylic alcohols by allylation reaction with aldehydes in the presence of iridium complex-catalyst.
  • The preparation of α-imino aldehydes.

Storage Class Code

10 - Combustible liquids

WGK

WGK 2

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

Preparation of α-imino aldehydes by [1, 3]-rearrangements of O-alkenyl oximes
Kontokosta D, et al.
Organic Letters, 15(18), 4830-4833 (2013)
Enantioselective synthesis of anti homoallylic alcohols from terminal alkynes and aldehydes based on concomitant use of a cationic iridium complex and a chiral phosphoric acid
Miura T, et al.
Journal of the American Chemical Society, 135(31), 11497-11500 (2013)
Palladium-catalyzed one-pot reaction of hydrazones, dihaloarenes, and organoboron reagents: Synthesis and cytotoxic activity of 1, 1-diarylethylene derivatives
Roche, M, et al.
The Journal of Organic Chemistry, 80(13), 6715-6727 (2015)

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service