(Dimethylphenylsilyl)boronic acid pinacol ester

Base Information

• Chemical Name: (Dimethylphenylsilyl)boronic acid pinacol ester
• CAS No.: 185990-03-8
• Molecular Formula: C14H23 B O2 Si
• Molecular Weight: 262.232
• European Community (EC) Number: 874-932-9
• DSSTox Substance ID: DTXSID00436709
• Nikkaji Number: J1.044.235D
• Wikidata: Q82251996
• Mol file: 185990-03-8.mol

Synonyms:185990-03-8;(Dimethylphenylsilyl)boronic acid pinacol ester;Dimethyl(phenyl)(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)silane;Dimethyl-phenyl-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)silane;2-(Dimethylphenylsilyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane;MFCD05664111;(DIMETHYLPHENYLSILYL)BORONIC ACID PINAC&;B-(dimethylphenylsilyl)pinacolborane;C14H23BO2Si;SCHEMBL12470176;DTXSID00436709;BCP13307;AKOS015908903;DS-7463;SY052857;(Dimethylphenylsilyl)boronicacidpinacolester;(DIMETHYLPHENYLSILYL)BORONICACIDPINAC&;CS-0038792;D4357;A50004;Dimethyl(phenyl)silylboronic Acid Pinacol Ester;(Dimethylphenylsilyl) boronic acid pinacol ester;A880691;J-011932;(Dimethylphenylsilyl)boronic acid pinacol ester, 95%;dimethyl(phenyl)(tetramethyl-1,3,2-dioxaborolan-2-yl)silane;2-(Dimethylphenylsilyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborole

Chemical Property of (Dimethylphenylsilyl)boronic acid pinacol ester

Chemical Property:

• Vapor Pressure: 0.014mmHg at 25°C
• Refractive Index: n20/D 1.4946
• Boiling Point: 266.887°C at 760 mmHg
• Flash Point: 110 °C
• PSA: 18.46000
• Density: 0.962 g/mL at 25 °C
• LogP: 2.77260
• Storage Temp.: Inert atmosphere,Room Temperature
• Solubility.: sol common organic solvents.
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 262.1560367
• Heavy Atom Count: 18
• Complexity: 293

Purity/Quality:

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

(Dimethylphenylsilyl)boronic acid pinacol ester ^*data from reagent suppliers

Safty Information:

• Pictogram(s): R10:Flammable.; R36/37/38:Irritating to eyes, respiratory system and skin.
• Hazard Codes: R10:Flammable.; R36/37/38:Irritating to eyes, respiratory system and skin.
• Statements: R10:Flammable.; R36/37/38:Irritating to eyes, respiratory system and skin.
• Safety Statements: S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.; S36:Wear suitable prot

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: B1(OC(C(O1)(C)C)(C)C)[Si](C)(C)C2=CC=CC=C2
• Physical properties: bp 97–99? C/0.1 mmHg.
• Uses: 2-(Dimethylphenylsilyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane is widely used as silaboration and silylation reagent for unsaturated organic compounds; a derivative having diethylamino group on the silicon atom for use as a precursor for silylene generation. (Dimethylphenylsilyl)boronic acid pinacol ester (Suginome′s reagent) can be used as a reagent: For the selective addition of dimethylphenylsilanyl group to cyclic and acyclic unsaturated ketones, esters, acrylonitriles using a copper catalyst. In the synthesis of (Z)-4-boryl-1-silyl-2-alkene derivatives by stereoselective addition of silicon-boron bond to acyclic 1,3-dienes in presence of Ni catalyst. In the preparation of silyl-substituted butenoate and β-silyl-substituted acrylate derivatives from allenes and propiolate derivatives via hydrosilylation reactions using a copper catalyst. In the palladium-catalyzed asymmetric silaboration of allenes and alkanes to offered corresponding β-borylallylsilanes and 2-boryl-1-silylalkanes respectively.

Technology Process of (Dimethylphenylsilyl)boronic acid pinacol ester

There total 15 articles about (Dimethylphenylsilyl)boronic acid pinacol ester 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: 93.0%

phenyldimethylsilyl chloride (768-33-2) + 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane (25015-63-8) → dimethylphenyl(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)silane (185990-03-8)

Guidance literature:

phenyldimethylsilyl chloride; With lithium; In tetrahydrofuran; at 0 ℃; for 6h; Inert atmosphere;

4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane; In tetrahydrofuran; hexane; at 0 - 22 ℃; for 12h; Inert atmosphere;

DOI:10.1002/chem.201203803

Reference yield: 80.0%

2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (61676-62-8) + phenyldimethylsilyl chloride (768-33-2) → dimethylphenyl(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)silane (185990-03-8)

Guidance literature:

phenyldimethylsilyl chloride; With lithium; In tetrahydrofuran; mineral oil; at 0 ℃; Inert atmosphere;

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

DOI:10.1002/chem.201000907

Reference yield: 79.0%

2,3-dimethyl-2,3-butane diol (76-09-5) + (bis(diethylamino)-boranyl)dimethylphenylsilane (166329-94-8) → dimethylphenyl(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)silane (185990-03-8)

Guidance literature:

In dichloromethane; at 20 ℃; for 10h;

DOI:10.1016/S0040-4020(99)00444-5

upstream raw materials:

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

(bis(diethylamino)-boranyl)dimethylphenylsilane

dimethyl(phenyl)silyl lithium

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

Downstream raw materials:

(Z)-dimethyl(phenyl)(2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)oct-1-en-1-yl)silane

3-cyclohexyl-3-(dimethylphenylsilyl)-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1-propene

3-(dimethylphenylsilyl)-5-phenyl-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1-pentene

Refernces

• 1、 Liu, Peng,Mai, Binh Khanh,Nafie, Jordan,O'Connor, Thomas J.,Toste, F. Dean. "Generation of Axially Chiral Fluoroallenes through a Copper-Catalyzed Enantioselective β-Fluoride Elimination". supporting information. p. 13759 - 13768. Retrieved 2021/09/07.
• 2、 Wang, Xiu,Wang, Zhenhua,Nishihara, Yasushi. "Nickel/copper-cocatalyzed decarbonylative silylation of acyl fluorides". supporting information. p. 10507 - 10510. Retrieved 2019/09/06.