4,4,5,5-Tetramethyl-2-(4-methylbenzyl)-1,3,2-dioxaborolane

Base Information

• Chemical Name: 4,4,5,5-Tetramethyl-2-(4-methylbenzyl)-1,3,2-dioxaborolane
• CAS No.: 356570-52-0
• Molecular Formula: C14H21BO2
• Molecular Weight: 232.131
• Hs Code.: 2934999090
• DSSTox Substance ID: DTXSID30584782
• Nikkaji Number: J1.670.087H
• Wikidata: Q82476503
• Mol file: 356570-52-0.mol

Synonyms:356570-52-0;4,4,5,5-Tetramethyl-2-(4-methylbenzyl)-1,3,2-dioxaborolane;4-Methylbenzylboronic acid pinacol ester;4,4,5,5-tetramethyl-2-[(4-methylphenyl)methyl]-1,3,2-dioxaborolane;4-Methylbenzylboronic acid, pinacol ester;2-(4-Methylbenzyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane;1,3,2-Dioxaborolane, 4,4,5,5-tetramethyl-2-[(4-methylphenyl)methyl]-;SCHEMBL711542;DTXSID30584782;MFCD08276847;AKOS016002042;AS-55662;CS-0061305;4-Methylbenzylboronic acid pinacol ester, 97%;EN300-763464;Y10551;4,4,5,5-tetramethyl-2-(4-methyl-benzyl)-1,3,2-dioxaborolane

Chemical Property of 4,4,5,5-Tetramethyl-2-(4-methylbenzyl)-1,3,2-dioxaborolane

Chemical Property:

• Vapor Pressure: 0.00378mmHg at 25°C
• Refractive Index: n20/D 1.489
• Boiling Point: 95oC/1 mmHg
• Flash Point: 110oC
• PSA: 18.46000
• Density: 0.953 g/mL at 25oC
• LogP: 3.43530
• Storage Temp.: 2-8°C
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 232.1634601
• Heavy Atom Count: 17
• Complexity: 251

Purity/Quality:

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

4,4,5,5-Tetramethyl-2-[(4-methylphenyl)methyl]-1,3,2-dioxaborolane ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: B1(OC(C(O1)(C)C)(C)C)CC2=CC=C(C=C2)C

Technology Process of 4,4,5,5-Tetramethyl-2-(4-methylbenzyl)-1,3,2-dioxaborolane

There total 26 articles about 4,4,5,5-Tetramethyl-2-(4-methylbenzyl)-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: 92.0%

para-bromotoluene (106-38-7) + 4,4,5,5-tetramethyl-2-[(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)methyl]-1,3,2-dioxaborolane (78782-17-9) → 4,4,5,5-tetramethyl-2-[(4-methylphenyl)methyl]-1,3,2-dioxaborolane (356570-52-0)

Guidance literature:

With bis(tri-t-butylphosphine)palladium⁽⁰⁾; potassium hydroxide; In 1,4-dioxane; water; at 25 ℃; for 5h; chemoselective reaction; Inert atmosphere;

DOI:10.1021/ol201115k

Reference yield: 92.0%

4-Methylbenzyl bromide (104-81-4) + 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane (25015-63-8) → 4,4,5,5-tetramethyl-2-[(4-methylphenyl)methyl]-1,3,2-dioxaborolane (356570-52-0)

Guidance literature:

With magnesium; triethylamine; In tetrahydrofuran; for 15h; Inert atmosphere; Reflux;

DOI:10.1021/ja1052973

Reference yield: 88.0%

para-xylene (106-42-3) + bis(pinacol)diborane (73183-34-3) → 4,4,5,5-tetramethyl-2-[(4-methylphenyl)methyl]-1,3,2-dioxaborolane (356570-52-0)

Guidance literature:

With 4'-(4-carboxyphenyl)-[2,2':6',2''-terpyridine]-5,5''-dicarboxylate-based metal-organic layers-stabilized Co(THF)_x complex; at 100 ℃; for 72h;

DOI:10.1039/c7sc03537c

upstream raw materials:

para-xylene

4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane

bis(pinacol)diborane

4-Methylbenzyl chloride

Downstream raw materials:

[6-fluoro-3-methyl-4-(4-methyl-benzyl)-naphthalen-2-yl]-acetic acid methyl ester

C₂₈H₃₁N₃O₃

4-methylethylbenzene

(1S)-1-chloro-2-(4-methylbenzyl)boronic acid (+)-pinanediol ester

Refernces

• 1、 Yoshii, Daichi,Yatabe, Takafumi,Yabe, Tomohiro,Yamaguchi, Kazuya. "C(sp3)-H selective benzylic borylation by in situ reduced ultrasmall Ni species on CeO2". . p. 2150 - 2155. Retrieved 2021/02/20.
• 2、 Klein, Markus,Busch, Michael,Friese-Hamim, Manja,Crosignani, Stefano,Fuchss, Thomas,Musil, Djordje,Rohdich, Felix,Sanderson, Michael P.,Seenisamy, Jeyaprakashnarayanan,Walter-Bausch, Gina,Zanelli, Ugo,Hewitt, Philip,Esdar, Christina,Schadt, Oliver. "Structure-Based Optimization and Discovery of M3258, a Specific Inhibitor of the Immunoproteasome Subunit LMP7 (β5i)". . p. 10230 - 10245. Retrieved 2021/07/26.