674729
3-(tert-Butyldimethylsilyloxy)-1-butyn-1-ylboronic acid pinacol ester
96%
Synonym(s):
2-((3-tert-Butyldimethylsilyloxy)-1-butyn-1-yl)-4,4,5,5-tetramethyl-(1,3,2)dioxaborolane
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About This Item
Empirical Formula (Hill Notation):
C16H31BO3Si
Molecular Weight:
310.31
UNSPSC Code:
12352103
PubChem Substance ID:
MDL number:
InChI
1S/C16H31BO3Si/c1-13(18-21(9,10)14(2,3)4)11-12-17-19-15(5,6)16(7,8)20-17/h13H,1-10H3
SMILES string
CC(O[Si](C)(C)C(C)(C)C)C#CB1OC(C)(C)C(C)(C)O1
InChI key
KGDJKWYVGUGRCG-UHFFFAOYSA-N
assay
96%
refractive index
n20/D 1.4488
density
0.9158 g/mL at 25 °C
storage temp.
2-8°C
Application
Alkynylboronates participate in a variety of regio- and stereoselective carbon-carbon bond forming
processes including enyne cross-metathesis and the Alder ene reaction.
processes including enyne cross-metathesis and the Alder ene reaction.
Storage Class
12 - Non Combustible Liquids
wgk
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
ppe
Eyeshields, Gloves, multi-purpose combination respirator cartridge (US)
Regulatory Information
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Mansuk Kim et al.
Organic letters, 7(9), 1865-1868 (2005-04-23)
[reaction: see text] Regio- and stereoselective enyne cross metathesis reactions between borylated alkynes and terminal alkenes were realized to provide a variety of functionalized vinyl boronates. High chemical yield and regioselectivity was achieved irrespective of substituents on the alkyne and
Eric C Hansen et al.
Journal of the American Chemical Society, 127(10), 3252-3253 (2005-03-10)
Ruthenium-catalyzed Alder ene reactions between borylated alkynes and terminal alkenes give the corresponding beta,beta-disubstituted vinyl boronates with high selectivity for the branched isomer. The stereochemistry of the vinyl boronate moiety was the result of a formal trans addition of the
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