2-(2,6-Difluoro-4-methoxyphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

Base Information

• Chemical Name: 2-(2,6-Difluoro-4-methoxyphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
• CAS No.: 1111096-19-5
• Molecular Formula: C₁₃H₁₇BF₂O₃
• Molecular Weight: 270.084
• DSSTox Substance ID: DTXSID101149874
• Nikkaji Number: J3.490.112K
• Mol file: 1111096-19-5.mol

Synonyms:1111096-19-5;2-(2,6-DIFLUORO-4-METHOXYPHENYL)-4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLANE;2,6-Difluoro-4-methoxyphenylboronic acid pinacol ester;SCHEMBL2524790;BXICLURBOWTZED-UHFFFAOYSA-N;DTXSID101149874;MFCD12405359;AKOS017550464;AT16083;BS-51083;CS-0088589;EN300-3256274;Z1336745230;2-(2,6-difluoro-4-methoxy-phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

Chemical Property of 2-(2,6-Difluoro-4-methoxyphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

Chemical Property:

• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 2
• Exact Mass: 270.1238809
• Heavy Atom Count: 19
• Complexity: 310

Purity/Quality:

97% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: B1(OC(C(O1)(C)C)(C)C)C2=C(C=C(C=C2F)OC)F

Technology Process of 2-(2,6-Difluoro-4-methoxyphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

There total 4 articles about 2-(2,6-Difluoro-4-methoxyphenyl)-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: 86.0%

3,5-difluoroanisol (93343-10-3) + 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane (25015-63-8) → 2-(2,6-difluoro-4-methoxyphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (1111096-19-5)

Guidance literature:

With (1,5-cyclooctadiene)(methoxy)iridium(I) dimer; 4,4'-di-tert-butyl-2,2'-bipyridine; In tetrahydrofuran; at 80 ℃; for 18h; Inert atmosphere;

DOI:10.1021/ol301570t

Reference yield: 74.0%

3,5-difluoroanisol (93343-10-3) + bis(pinacol)diborane (73183-34-3) → 2-(2,6-difluoro-4-methoxyphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (1111096-19-5)

Guidance literature:

With (1,5-cyclooctadiene)(methoxy)iridium(I) dimer; 4,4'-di-tert-butyl-2,2'-bipyridine; In tetrahydrofuran; at 80 ℃; for 18h; Inert atmosphere;

DOI:10.1021/ol301570t

Reference yield: 20.0%

(2,6-difluoro-4-methoxyphenyl)boronic acid (406482-20-0) + 2,3-dimethyl-2,3-butane diol (76-09-5) → 2-(2,6-difluoro-4-methoxyphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (1111096-19-5) + water (7732-18-5)

Guidance literature:

In acetonitrile; at 20 ℃; Solvent; Equilibrium constant; Molecular sieve;

DOI:10.1021/jacs.1c06863

upstream raw materials:

3,5-difluoroanisol

bis(pinacol)diborane

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

(2,6-difluoro-4-methoxyphenyl)boronic acid

Downstream raw materials:

4,4,5,5-tetramethyl-2-(2,3,4,5,6-pentafluorophenyl)-1,3,2-dioxaborolane

5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolane-2-yl)-1,3-thiazole

(2,6-difluoro-4-methoxyphenyl)boronic acid

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