2-(3-Chlorobenzyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

Base Information

• Chemical Name: 2-(3-Chlorobenzyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
• CAS No.: 517920-59-1
• Molecular Formula: C13H18BClO2
• Molecular Weight: 252.549
• Hs Code.: 2934999090
• DSSTox Substance ID: DTXSID60697056
• Nikkaji Number: J1.857.031I
• Wikidata: Q82626868
• Mol file: 517920-59-1.mol

Synonyms:517920-59-1;2-(3-CHLOROBENZYL)-4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLANE;2-[(3-chlorophenyl)methyl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane;MFCD10698516;3-Chlorobenzylboronic Acid Pinacol Ester;(3-CHLOROBENZYL)BORONIC ACID PINACOL ESTER;SCHEMBL712014;DTXSID60697056;AKOS015995071;AB62278;AM85098;SY013352;CS-0041425;EN300-763462;A871179;J-505775;1,3,2-DIOXABOROLANE, 2-[(3-CHLOROPHENYL)METHYL]-4,4,5,5-TETRAMETHYL-

Chemical Property of 2-(3-Chlorobenzyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

Chemical Property:

• Boiling Point: 298.8±23.0 °C(Predicted)
• PSA: 18.46000
• Density: 1.08±0.1 g/cm3(Predicted)
• LogP: 3.78030
• Storage Temp.: 2-8°C
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 252.1088377
• Heavy Atom Count: 17
• Complexity: 265

Purity/Quality:

99% ^*data from raw suppliers

2-[(3-chlorophenyl)methyl]-4,4,5,5-tetramethyl-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)CC2=CC(=CC=C2)Cl

Technology Process of 2-(3-Chlorobenzyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

There total 28 articles about 2-(3-Chlorobenzyl)-4,4,5,5-tetramethyl-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: 91.0%

1-Chloro-3-chloromethyl-benzene (620-20-2,130468-19-8) + bis(pinacol)diborane (73183-34-3) → 2-(3-chlorobenzyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (517920-59-1)

Guidance literature:

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium carbonate; In 1,4-dioxane; at 100 ℃; for 18h;

DOI:10.1016/S0040-4039(02)02566-2

Reference yield: 90.0%

4-chlorobenzyl bromide (622-95-7) + 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane (25015-63-8) → 2-[(4-chlorophenyl)methyl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (517920-59-1)

Guidance literature:

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

DOI:10.1021/ja1052973

Reference yield: 85.0%

1-Chloro-4-(chloromethyl)benzene (104-83-6) + bis(pinacol)diborane (73183-34-3) → 2-[(4-chlorophenyl)methyl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (517920-59-1)

Guidance literature:

With potassium acetate; In toluene; mixt. of B compd., aryl halide, Pd(dba)2 complex, (4-MeOC6H4)3P, KOAc and toluene stirred for 24 h at 50°C;

DOI:10.1246/cl.2002.780

upstream raw materials:

1-Chloro-3-chloromethyl-benzene

bis(pinacol)diborane

1-chloro-3-methylbenzene

tert-butyldimethyl(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)silane

Downstream raw materials:

4-chloro(ethylbenzene)

Refernces

• 1、 Yang, Ling,Tan, Dong-Hang,Fan, Wen-Xin,Liu, Xu-Ge,Wu, Jia-Qiang,Huang, Zhi-Shu,Li, Qingjiang,Wang, Honggen. "Photochemical Radical C–H Halogenation of Benzyl N-Methyliminodiacetyl (MIDA) Boronates: Synthesis of α-Functionalized Alkyl Boronates". supporting information. p. 3454 - 3458. Retrieved 2020/12/17.
• 2、 Suzuki, Kensuke,Nishimoto, Yoshihiro,Yasuda, Makoto. "(o-Phenylenediamino)borylstannanes: Efficient Reagents for Borylation of Various Alkyl Radical Precursors". supporting information. p. 3968 - 3973. Retrieved 2020/12/30.