3-(Trimethylsilyl)phenylboronic acid

Base Information

• Chemical Name: 3-(Trimethylsilyl)phenylboronic acid
• CAS No.: 177171-16-3
• Molecular Formula: C9H15BO2Si
• Molecular Weight: 194.113
• Hs Code.: 29319090
• European Community (EC) Number: 804-982-9
• DSSTox Substance ID: DTXSID30404456
• Nikkaji Number: J2.545.533I
• Wikidata: Q72514540
• Mol file: 177171-16-3.mol

Synonyms:177171-16-3;3-(Trimethylsilyl)phenylboronic acid;3-Trimethylsilylphenylboronic acid;(3-(Trimethylsilyl)phenyl)boronic acid;(3-trimethylsilylphenyl)boronic Acid;Boronic acid, B-[3-(trimethylsilyl)phenyl]-;MFCD03093884;[3-(trimethylsilyl)phenyl]boronic acid;Boronic acid, [3-(trimethylsilyl)phenyl]-;3-(Trimethylsilyl)benzeneboronic Acid;SCHEMBL646948;DTXSID30404456;REMKRZLFPLDTKR-UHFFFAOYSA-N;3-trimethylsilyl-phenylboronic acid;BCP09618;CHA17116;(3-(Trimethylsilyl)phenyl)boronicacid;AKOS004119268;AB13273;AM90067;CS-W010668;AS-15098;SY031637;1-(2-FLUOROPHENYL)CYCLOPROPYLAMINE;FT-0643715;T2663;EN300-714509;3-(Trimethylsilyl)phenylboronic acid, >=95.0%;A812241;J-513125;Z1255365353;(3-trimethylsilylphenyl)boronic acid

Chemical Property of 3-(Trimethylsilyl)phenylboronic acid

Chemical Property:

• Vapor Pressure: 0.00097mmHg at 25°C
• Melting Point: 145-150 °C(lit.)
• Refractive Index: 1.494
• Boiling Point: 290.2 °C at 760 mmHg
• PKA: 8.73±0.10(Predicted)
• Flash Point: 129.3 °C
• PSA: 40.46000
• Density: 1.01 g/cm³
• LogP: -0.08840
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• Solubility.: soluble in Methanol
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 194.0934364
• Heavy Atom Count: 13
• Complexity: 168

Purity/Quality:

98% ^*data from raw suppliers

3-(Trimethylsilyl)phenylboronic acid ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: B(C1=CC(=CC=C1)[Si](C)(C)C)(O)O
• Uses: 3-(Trimethylsilyl)phenylboronic acid can be used:To prepare a 2-phenylpyridine ligand, which is used in the synthesis of Ir(III) complex applicable in the OLEDs.As an intermediate in the preparation of biphenyl derived amino acids.As a starting material for the synthesis of triphenylene-based electron transport materials.

Technology Process of 3-(Trimethylsilyl)phenylboronic acid

There total 3 articles about 3-(Trimethylsilyl)phenylboronic 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: 86.0%

Trimethyl borate (121-43-7,63156-11-6) + (3-bromophenyl)trimethylsilane (17878-47-6) + tert.-butyl lithium (594-19-4) → 3-(trimethylsilyl)phenylboronic acid (177171-16-3)

Guidance literature:

With hydrogenchloride; In water; pentane;

Reference yield:

1,3-dibromobenzene (108-36-1) → 3-(trimethylsilyl)phenylboronic acid (177171-16-3)

Guidance literature:

Multi-step reaction with 2 steps

1.1: BuLi / diethyl ether

1.2: diethyl ether

2.1: BuLi / diethyl ether

2.2: diethyl ether

With n-butyllithium; In diethyl ether;

DOI:10.1080/15421400500365243

Reference yield:

triethyl borane (97-94-9) + (3-bromophenyl)trimethylsilane (17878-47-6) → 3-(trimethylsilyl)phenylboronic acid (177171-16-3)

Guidance literature:

(3-bromophenyl)trimethylsilane; With n-butyllithium; In diethyl ether;

triethyl borane; In diethyl ether;

DOI:10.1080/15421400500365243

upstream raw materials:

triethyl borane

(3-bromophenyl)trimethylsilane

1,3-dibromobenzene

Trimethyl borate

Downstream raw materials:

4-methyl-2-(3-trimethylsilanyl-phenyl)-pyridine

2,5-Di(3-(trimethylsilyl)phenyl)pyridine

3,3'-dibromo-9,9'-spirobi[fluorene]

4'-(trifluoromethyl)-[1,1'-biphenyl]-3-ol

Refernces

• 1、 -. "Highly Branched Dendrimers". . . Retrieved 2008/12/08.