triMethyl((4,4,5,5-tetraMethyl-1,3,2-dioxaborolan-2-yl)ethynyl)silane

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triMethyl((4,4,5,5-tetraMethyl-1,3,2-dioxaborolan-2-yl)ethynyl)silane manufacturers

triMethyl((4,4,5,5-tetraMethyl-1,3,2-dioxaborolan-2-yl)ethynyl)silane Basic information
Product Name:triMethyl((4,4,5,5-tetraMethyl-1,3,2-dioxaborolan-2-yl)ethynyl)silane
Synonyms:triMethyl((4,4,5,5-tetraMethyl-1,3,2-dioxaborolan-2-yl)ethynyl)silane;4,4,5,5-TetraMethyl-2-triMethylsilanylethynyl-[1,3,2]dioxaborolane;(trimethylsilyl)ethynylboronic acid pinacol ester;trimethyl(2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)ethynyl)silane;4,4,5,5-tetramethyl-2-[2-(trimethylsilanyl) ethynyl][1,3,2]dioxaborolane;4,4,5,5-tetramethyl-2-[2-(trimethylsilyl)ethynyl]-1,3,2-Dioxaborolane;1,3,2-Dioxaborolane, 4,4,5,5-tetramethyl-2-[(trimethylsilyl)ethynyl]-;1,3,2-Dioxaborolane, 4,4,5,5-tetramethyl-2-[2-(trimethylsilyl)ethynyl]-
CAS:159087-46-4
MF:C11H21BO2Si
MW:224.18
EINECS:
Product Categories:organoboron
Mol File:159087-46-4.mol
triMethyl((4,4,5,5-tetraMethyl-1,3,2-dioxaborolan-2-yl)ethynyl)silane Structure
triMethyl((4,4,5,5-tetraMethyl-1,3,2-dioxaborolan-2-yl)ethynyl)silane Chemical Properties
Boiling point 211.1±23.0 °C(Predicted)
density 0.91±0.1 g/cm3(Predicted)
storage temp. under inert gas (nitrogen or Argon) at 2-8°C
AppearanceWhite to off-white Solid
Safety Information
HS Code 2931900090
MSDS Information
triMethyl((4,4,5,5-tetraMethyl-1,3,2-dioxaborolan-2-yl)ethynyl)silane Usage And Synthesis
Synthesis
2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

61676-62-8

Trimethylsilylacetylene

1066-54-2

triMethyl((4,4,5,5-tetraMethyl-1,3,2-dioxaborolan-2-yl)ethynyl)silane

159087-46-4

GENERAL METHODS: A mixture of isopropanol pinacol borate (0.5 mmol), trimethylsilyl acetylene (0.75 mmol), PPh3 with L1 and AgCl (1 mol%), and Cs2CO3 (1.1 mmol) in DMF (5 mL) was stirred for 24 hr at 50°C in an Ar atmosphere. After completion of the reaction, the reaction mixture was acidified with 1 M hydrochloric acid solution in an ice-water bath and the aqueous phase was extracted with ethyl acetate (three times). The combined organic layers were washed with brine, dried with Na2SO4 and subsequently concentrated under reduced pressure. The crude product was purified by silica gel column chromatography to afford 4,4,5,5-tetramethyl-2-trimethylsilylalkynyl-[1,3,2]dioxaborolane.

References[1] Tetrahedron, 2014, vol. 70, # 35, p. 5815 - 5819
[2] Tetrahedron, 2013, vol. 69, # 5, p. 1546 - 1552
[3] Patent: WO2016/97870, 2016, A1. Location in patent: Page/Page column 0174
[4] Patent: WO2013/52394, 2013, A1. Location in patent: Paragraph 00253
[5] Journal of Organic Chemistry, 2013, vol. 78, # 23, p. 11637 - 11645
triMethyl((4,4,5,5-tetraMethyl-1,3,2-dioxaborolan-2-yl)ethynyl)silane Preparation Products And Raw materials
Raw materials2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane-->Trimethylsilylacetylene-->Silver chloride-->Cesium carbonate-->N,N-Dimethylformamide-->Triphenylphosphine
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