4,4,5,5-Tetramethyl-2-(4-trimethylsilanylethynyl-phenyl)-[1,3,2]dioxaborolane

Base Information

• Chemical Name: 4,4,5,5-Tetramethyl-2-(4-trimethylsilanylethynyl-phenyl)-[1,3,2]dioxaborolane
• CAS No.: 870238-65-6
• Molecular Formula: C17H25 B O2 Si
• Molecular Weight: 300.281
• Hs Code.: 2934999090
• European Community (EC) Number: 623-418-0
• DSSTox Substance ID: DTXSID10592229
• Nikkaji Number: J2.968.571A
• Wikidata: Q82486221
• Mol file: 870238-65-6.mol

Synonyms:870238-65-6;4,4,5,5-Tetramethyl-2-(4-trimethylsilanylethynyl-phenyl)-[1,3,2]dioxaborolane;trimethyl-[2-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]ethynyl]silane;4-(Trimethylsilyl)ethynylphenylboronic acid pinacol ester;Trimethyl((4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)ethynyl)silane;trimethyl({2-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]ethynyl})silane;4-[(Trimethylsilyl)ethynyl]benzeneboronic acid pinacol ester;4,4,5,5-Tetramethyl-2-[4-[(trimethylsilyl)ethynyl]phenyl]-1,3,2-dioxaborolane;4-[(Trimethylsilyl)ethynyl]phenylboronic acid pinacol ester;4,4,5,5-Tetramethyl-2-(4-[(trimethylsilyl)ethynyl]phenyl)-1,3,2-dioxaborolane;Trimethyl{[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]ethynyl}silane;1,3,2-Dioxaborolane,4,4,5,5-tetramethyl-2-[4-[2-(trimethylsilyl)ethynyl]phenyl]-;SCHEMBL15574346;DTXSID10592229;MFCD08706286;AKOS016339822;AS-2408;4-(4,4,5,5-TETRAMETHYL-[1,3,2]DIOXABOROLAN-2-YL)-PHENYLETHYNYL-TRIMETHYLSILANE;TRIMETHYL({2-[4-(TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)PHENYL]ETHYNYL})SILANE;CS-0175599;EN300-7375564;A922944;Z2049757974;4-[(Trimethylsilyl)ethynyl]phenylboronic acid pinacol ester, 97%

Chemical Property of 4,4,5,5-Tetramethyl-2-(4-trimethylsilanylethynyl-phenyl)-[1,3,2]dioxaborolane

Chemical Property:

• PSA: 18.46000
• LogP: 3.21470
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 3
• Exact Mass: 300.1716867
• Heavy Atom Count: 21
• Complexity: 428

Purity/Quality:

98%,99%, ^*data from raw suppliers

4,4,5,5-Tetramethyl-2-(4-trimethylsilanylethynyl-phenyl)-[1,3,2]dioxaborolane ^*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)C2=CC=C(C=C2)C#C[Si](C)(C)C

Technology Process of 4,4,5,5-Tetramethyl-2-(4-trimethylsilanylethynyl-phenyl)-[1,3,2]dioxaborolane

There total 15 articles about 4,4,5,5-Tetramethyl-2-(4-trimethylsilanylethynyl-phenyl)-[1,3,2]dioxaborolane 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: 98.0%

2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (61676-62-8) + (4-bromophenyl)(trimethylsilyl)acetylene (16116-78-2) → ((4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)ethynyl)trimethylsilane (870238-65-6)

Guidance literature:

(4-bromophenyl)(trimethylsilyl)acetylene; With n-butyllithium; In tetrahydrofuran; hexane; at -78 ℃; for 0.5h; Inert atmosphere;

2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane; In tetrahydrofuran; hexane; at -20 - 20 ℃; Inert atmosphere;

DOI:10.1002/anie.201814342

Reference yield: 96.0%

3-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)acetylene (1034287-04-1) + trimethylsilyl iodide (16029-98-4) → ((4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)ethynyl)trimethylsilane (870238-65-6)

Guidance literature:

With [{Ir(μ-Cl)(CO)2}2]; N-ethyl-N,N-diisopropylamine; In toluene; at 80 ℃; for 24h; Schlenk technique; Inert atmosphere;

DOI:10.1016/j.tetlet.2013.11.103

Reference yield: 96.0%

→ ((4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)ethynyl)trimethylsilane (870238-65-6)

Guidance literature:

upstream raw materials:

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

4-[(trimethylsilyl)ethynyl]phenyl boronic acid

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

(4-bromophenyl)(trimethylsilyl)acetylene

Downstream raw materials:

C₃₇H₄₀N₂Si₂

4,4,5,5-tetramethyl-2-[4-(2-phenylethynyl)phenyl]-1,3,2-dioxaborolane

4-(trimethylsilylethynyl)phenyl azide

Refernces

• 1、 -. "Fluorescent probe for detecting active oxygen molecule and preparation method and application thereof". . . Retrieved 2021/10/27.
• 2、 Schlimm, Alexander,L?w, Roland,Rusch, Talina,R?hricht, Fynn,Strunskus, Thomas,Tellkamp, Tobias,S?nnichsen, Frank,Manthe, Uwe,Magnussen, Olaf,Tuczek, Felix,Herges, Rainer. "Long-Distance Rate Acceleration by Bulk Gold". supporting information. p. 6574 - 6578. Retrieved 2019/04/26.