(5-(Trimethylsilyl)thiophen-2-yl)boronic acid

Base Information

• Chemical Name: (5-(Trimethylsilyl)thiophen-2-yl)boronic acid
• CAS No.: 138983-68-3
• Molecular Formula: C₇H₁₃BO₂SSi
• Molecular Weight: 200.142
• DSSTox Substance ID: DTXSID50570445
• Wikidata: Q82457890
• Mol file: 138983-68-3.mol

Synonyms:138983-68-3;(5-(Trimethylsilyl)thiophen-2-yl)boronic acid;5-(TRIMETHYLSILYL)THIOPHEN-2-YLBORONIC ACID;(5-trimethylsilylthiophen-2-yl)boronic acid;Boronic acid, [5-(trimethylsilyl)-2-thienyl]- (9CI);[5-(Trimethylsilyl)thiophen-2-yl]boronic acid;5-TRIMETHYLSILYLTHIOPHENE-2-BORONIC ACID;5-TRIMETHYLSILYLTHIOPHENE-2-BORONICACID;DTXSID50570445;AKOS005254569;EN300-2356312;Boronic acid,[5-(trimethylsilyl)-2-thienyl]-(9ci)

Chemical Property of (5-(Trimethylsilyl)thiophen-2-yl)boronic acid

Chemical Property:

• Boiling Point: 298.9°Cat760mmHg
• Flash Point: 134.6°C
• PSA: 68.70000
• Density: 1.1g/cm³
• LogP: -0.02690
• Storage Temp.: 2-8°C
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 200.0498575
• Heavy Atom Count: 12
• Complexity: 160

Purity/Quality:

98%min ^*data from raw suppliers

(5-(Trimethylsilyl)thiophen-2-yl)boronicacid 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: B(C1=CC=C(S1)[Si](C)(C)C)(O)O

Technology Process of (5-(Trimethylsilyl)thiophen-2-yl)boronic acid

There total 2 articles about (5-(Trimethylsilyl)thiophen-2-yl)boronic acid 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: 57.0%

2-bromo-5-trimethylsilylthiophene (18246-28-1) + Trimethyl borate (121-43-7,63156-11-6) → 2-(trimethylsilyl)thiophene (18245-28-8) + 5-(trimethylsilyl)thiophene-2-carbaldehyde (13960-01-5) + 2-(trimethylsilyl)-5-thienyl boronic acid (138983-68-3)

Guidance literature:

With aluminium; In N,N-dimethyl-formamide; byproducts: Al(3+); Electrolysis; electrolysis carried out in a single-compartment cell at room temp., starting materials dissolved in DMF containing KBr or n-Bu4NBr, solvent andexcess B(OCH3)3 evaporated under vacuum, medium hydrolysed at 0° C with an HCl or H2SO4 soln.; extraction with Et2O (3 x 20 ml if the solvent evaporated or 3 x 60 ml otherwise), dried over sodium or magnesium sulfate and concentrated undervacuum, side product phenol formation avoided by work-up under inert at mosphere, recrystallized in CH2Cl2;

DOI:10.1039/b200744b

Reference yield:

2-bromo-5-trimethylsilylthiophene (18246-28-1) → 2-(trimethylsilyl)-5-thienyl boronic acid (138983-68-3)

Guidance literature:

2-bromo-5-trimethylsilylthiophene; With Trimethyl borate; In N,N-dimethyl-formamide; at 20 ℃; Electrochemical reaction; Al consumable anode, supporting electrolyte;

at 0 ℃; Further stages.; Acid hydrolysis;

DOI:10.1039/b200744b

upstream raw materials:

2-bromo-5-trimethylsilylthiophene

Trimethyl borate

Refernces