Trimethyl((4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-YL)ethynyl)silane

Base Information

• Chemical Name: Trimethyl((4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-YL)ethynyl)silane
• CAS No.: 159087-46-4
• Molecular Formula: C11H21BO2Si
• Molecular Weight: 224.183
• Hs Code.: 2934999090
• European Community (EC) Number: 804-793-1
• DSSTox Substance ID: DTXSID00466167
• Nikkaji Number: J618.796J
• Wikidata: Q82292661
• Mol file: 159087-46-4.mol

Synonyms:159087-46-4;TRIMETHYL((4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)ETHYNYL)SILANE;(TRIMETHYLSILYL)ETHYNYLBORONIC ACID PINACOL ESTER;Trimethyl-[2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)ethynyl]silane;1,3,2-Dioxaborolane, 4,4,5,5-tetramethyl-2-[(trimethylsilyl)ethynyl]-;4,4,5,5-TETRAMETHYL-2-TRIMETHYLSILANYLETHYNYL-[1,3,2]DIOXABOROLANE;MFCD13182130;Trimethyl[(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)ethynyl]silane;Trimethyl[2-(tetramethyl-1,3,2-dioxaborolan-2-yl)ethynyl]silane;1,3,2-Dioxaborolane, 4,4,5,5-tetramethyl-2-[2-(trimethylsilyl)ethynyl]-;trimethyl[2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)ethynyl]silane;C11H21BO2Si;trimethyl(2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)ethynyl)silane;SCHEMBL14844606;((TRIMETHYLSILYL)ETHYNYL)BORONIC ACID PINACOL ESTER;DTXSID00466167;AMY37298;ZB0243;AKOS016347704;AB66712;AS-1004;CS-W000113;SY032334;FT-0726757;EN300-109633;A852766;[(Trimethylsilyl)ethynyl]boronic acid, pinacol ester;Z1424933096

Chemical Property of Trimethyl((4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-YL)ethynyl)silane

Chemical Property:

• Boiling Point: 211.1±23.0 °C(Predicted)
• PSA: 18.46000
• Density: 0.91±0.1 g/cm3(Predicted)
• LogP: 2.49860
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 224.1403866
• Heavy Atom Count: 15
• Complexity: 301

Purity/Quality:

98%min ^*data from raw suppliers

Trimethyl((4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)ethynyl)silane 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: B1(OC(C(O1)(C)C)(C)C)C#C[Si](C)(C)C

Technology Process of Trimethyl((4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-YL)ethynyl)silane

There total 7 articles about Trimethyl((4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-YL)ethynyl)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: 99.0%

4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane (25015-63-8) + trimethylsilylacetylene (1066-54-2) → 4,4,5,5-tetramethyl-2-trimethylsilanylethynyl-[1,3,2]dioxaborolane (159087-46-4)

Guidance literature:

With Cu⁽¹⁺⁾*CF₃O₃S^(1-)*C₂₂H₃₅N; triethylamine; In benzene; at 20 ℃; for 12h;

DOI:10.1039/c6sc02668k

Reference yield: 89.0%

4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane (25015-63-8) + trimethylsilylacetylene (1066-54-2) → 1-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2-trimethylsilylethene + 4,4,5,5-tetramethyl-2-trimethylsilanylethynyl-[1,3,2]dioxaborolane (159087-46-4)

Guidance literature:

With 1,4-diaza-bicyclo[2.2.2]octane; iron(II) triflate; In toluene; at 100 ℃; for 72h; chemoselective reaction; Inert atmosphere; Schlenk technique;

DOI:10.1002/adsc.201800588

Reference yield: 88.0%

2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (61676-62-8) + trimethylsilylacetylene (1066-54-2) → 4,4,5,5-tetramethyl-2-trimethylsilanylethynyl-[1,3,2]dioxaborolane (159087-46-4)

Guidance literature:

With C₁₅H₁₄N₄; caesium carbonate; triphenylphosphine; silver(I) chloride; In N,N-dimethyl-formamide; at 50 ℃; for 24h; Inert atmosphere; Schlenk technique;

DOI:10.1016/j.tet.2014.06.033

upstream raw materials:

bis(pinacol)diborane

Bis(trimethylsilyl)ethyne

2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

trimethylsilylacetylene

Refernces

• 1、 Buendia, Mikkel B.,Balin, Jan-Georges J.,Andersen, Mette E.,Lian, Zhong,Kramer, Soren. "Copper-Catalyzed Alkynylation of Benzylic C-H Bonds with Alkynylboronic Esters". . p. 150 - 154. Retrieved 2022.
• 2、 -. "Method for removing hydroboration of aluminum chloride catalytic terminal group alkyne". Paragraph 0063-0065. . Retrieved 2021/10/16.