(E)-Trimethyl(2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)vinyl)silane

Base Information

• Chemical Name: (E)-Trimethyl(2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)vinyl)silane
• CAS No.: 126688-99-1
• Molecular Formula: C11H23 B O2 Si
• Molecular Weight: 226.199
• Hs Code.: 2931900090
• European Community (EC) Number: 681-199-7
• Nikkaji Number: J396.326H
• Mol file: 126688-99-1.mol

Synonyms:126688-99-1;(E)-Trimethyl(2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)vinyl)silane;2-(TRIMETHYLSILYL)VINYLBORONIC ACID PINACOL ESTER;1,3,2-Dioxaborolane, 4,4,5,5-tetramethyl-2-[(1E)-2-(trimethylsilyl)ethenyl]-;trimethyl-[(E)-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)ethenyl]silane;Trimethyl(2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)vinyl)silane;608534-34-5;DAMNKYZWPOUBAV-CMDGGOBGSA-N;2-(Trimethylsilyl)vinylboronic acid piunacol ester;SCHEMBL11029208;SCHEMBL11029218;Trimethyl[2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)ethenyl]silane;MFCD03788735;AKOS025293751;CS-0264800;F87049;EN300-9460766;A889385;EN300-18635170;J-005420;Z1509557415;2-(Trimethylsilyl)vinylboronic acid pinacol ester, AldrichCPR;trimethyl[2-(tetramethyl-1,3,2-dioxaborolan-2-yl)ethenyl]silane;trimethyl[(E)-2-(tetramethyl-1,3,2-dioxaborolan-2-yl)ethenyl]silane;(E)-Timethyl(2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)vinyl)silane

Chemical Property of (E)-Trimethyl(2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)vinyl)silane

Chemical Property:

• Vapor Pressure: 0.546mmHg at 25°C
• Refractive Index: 1.433
• Boiling Point: 196.9°Cat760mmHg
• Flash Point: 72.9°C
• PSA: 18.46000
• Density: 0.88g/cm³
• LogP: 3.05140
• Sensitive.: Moisture Sensitive
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 226.1560367
• Heavy Atom Count: 15
• Complexity: 250

Purity/Quality:

97% ^*data from raw suppliers

2-(TRIMETHYLSILYL)VINYLBORONIC ACID PINACOL ESTER 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s): R36/37/38:Irritating to eyes, respiratory system and skin.
• Hazard Codes: R36/37/38:Irritating to eyes, respiratory system and skin.
• Statements: 36/37/38
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: B1(OC(C(O1)(C)C)(C)C)C=C[Si](C)(C)C
• Isomeric SMILES: B1(OC(C(O1)(C)C)(C)C)/C=C/[Si](C)(C)C

Technology Process of (E)-Trimethyl(2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)vinyl)silane

There total 4 articles about (E)-Trimethyl(2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)vinyl)silane which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 95.0%

4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane (25015-63-8) + trimethylsilylacetylene (1066-54-2) → (E)-trimethyl(2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)ethen-1-yl)silane (126688-99-1)

Guidance literature:

With tris(2,4,6-trifluorophenyl)borane triethylphosphine oxide; In dichloromethane; at 60 ℃; for 6h; Inert atmosphere; Sealed tube;

DOI:10.1002/chem.201703109

Reference yield: 42.0%

2,3-dimethyl-2,3-butane diol (76-09-5) + trimethylsilylacetylene (1066-54-2) → 1-trimethylsilyl-1-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)ethene + (E)-trimethyl(2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)ethen-1-yl)silane (126688-99-1)

Guidance literature:

Multistep reaction;

DOI:10.1002/anie.200351312

Reference yield: 25.0%

bis(pinacol)diborane (73183-34-3) + trimethylsilylacetylene (1066-54-2) → (E)-trimethyl(2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)ethen-1-yl)silane (126688-99-1)

Guidance literature:

bis(pinacol)diborane; With 1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazolium chloride; copper(l) chloride; sodium t-butanolate; In tetrahydrofuran; for 0.166667h; Inert atmosphere; Schlenk technique;

trimethylsilylacetylene; With methanol; In tetrahydrofuran; at 20 ℃; for 12h; stereoselective reaction; Inert atmosphere; Schlenk technique;

DOI:10.1002/adsc.201300881

upstream raw materials:

2,3-dimethyl-2,3-butane diol

trimethylsilylacetylene

bis(pinacol)diborane

4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane

Downstream raw materials:

(E)-methyl 6-amino-2-(4-chloro-2,3-difluorophenyl)-5-(2-(trimethylsilyl)vinyl)pyrimidine-4-carboxylate

(1E,3E)-1,4-bis(trimethylsilyl)-1,3-butadiene