588849
trans-4-(tert-Butyldimethylsiloxy)-1-buten-1-ylboronic acid pinacol ester
95%
Synonym(s):
trans-2-[4-(tert-butyldimethylsilyloxy)-1-buten-1-yl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
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About This Item
Empirical Formula (Hill Notation):
C16H33BO3Si
CAS Number:
Molecular Weight:
312.33
UNSPSC Code:
12352103
PubChem Substance ID:
MDL number:
InChI
1S/C16H33BO3Si/c1-14(2,3)21(8,9)18-13-11-10-12-17-19-15(4,5)16(6,7)20-17/h10,12H,11,13H2,1-9H3/b12-10+
SMILES string
CC(C)(C)[Si](C)(C)OCC\C=C\B1OC(C)(C)C(C)(C)O1
InChI key
ODTSJDLTXNDTBB-ZRDIBKRKSA-N
assay
95%
refractive index
n20/D 1.4470 (lit.)
bp
297-298 °C (lit.)
density
0.888 g/mL at 25 °C (lit.)
Application
trans-4-(tert-Butyldimethylsiloxy)-1-buten-1-ylboronic acid pinacol ester can be used as a substrate:
- In the catalyst-free Zweifel olefination of alkenyl boronic esters using triorganocerium reagents.
- In the study of carbosulfenylation reactions of alkenylboronates.
- To prepare chiral tris(boronates), which are important building blocks for preparing synthetically challenging compounds.
Storage Class
10 - Combustible liquids
wgk
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
ppe
Eyeshields, Gloves
Regulatory Information
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Find documentation for the products that you have recently purchased in the Document Library.
Enantiomerically enriched tris (boronates): readily accessible conjunctive reagents for asymmetric synthesis
Coombs JR, et al.
Journal of the American Chemical Society, 136(46), 16140-16143 (2014)
Enantioselective, Lewis Base-Catalyzed Carbosulfenylation of Alkenylboronates by 1, 2-Boronate Migration
Tao Z, et al.
Journal of the American Chemical Society, 140(46), 15621-15625 (2018)
Catalyst-Free Enantiospecific Olefination with In Situ Generated Organocerium Species
Music A, et al.
Angewandte Chemie (International ed. in English), 58(4), 1188-1192 (2019)
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