2-(2-(Difluoromethoxy)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

Base Information

• Chemical Name: 2-(2-(Difluoromethoxy)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
• CAS No.: 960067-33-8
• Molecular Formula: C13H17BF2O3
• Molecular Weight: 270.084
• Hs Code.: 2934999090
• European Community (EC) Number: 851-225-3
• DSSTox Substance ID: DTXSID60681915
• Wikidata: Q82606095
• Mol file: 960067-33-8.mol

Synonyms:960067-33-8;2-(2-(DIFLUOROMETHOXY)PHENYL)-4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLANE;2-[2-(difluoromethoxy)phenyl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane;2-DIFLUOROMETHOXYPHENYLBORONIC ACID, PINACOL ESTER;(2-(DIFLUOROMETHOXY)PHENYL)BORONIC ACID PINACOL ESTER;SCHEMBL263386;DTXSID60681915;TQU0315;MFCD16996403;AKOS015999396;MB20684;AS-49799;CS-0153837;EN300-190623;N10648;2-Difluoromethoxyphenylboronic acid pinacol ester;A845529;2-(Difluoromethoxy)benzeneboronic acid pinacol ester;2-(Difluoromethoxy)benzeneboronic acid, pinacol ester;Z1336745379;2-(2-difluoromethoxy-phenyl)-4,4,5,5-tetramethyl-[1,3,2]dioxaborolane;Difluoromethyl 2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl ether

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

Chemical Property:

• Boiling Point: 326.5±37.0 °C(Predicted)
• PSA: 27.69000
• Density: 1.13±0.1 g/cm3(Predicted)
• LogP: 2.58720
• Storage Temp.: Refrigerated.
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 3
• Exact Mass: 270.1238809
• Heavy Atom Count: 19
• Complexity: 307

Purity/Quality:

95% ^*data from raw suppliers

2-DifluoromethoxyphenylboronicAcid,PinacolEster ^*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)C2=CC=CC=C2OC(F)F
• Uses: 2-Difluoromethoxyphenylboronic Acid, Pinacol Ester is an intermediate in preparation of pyridine derivatives as voltage-gated sodium channel modulators useful in the treatment of pain.

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

There total 3 articles about 2-(2-(Difluoromethoxy)phenyl)-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: 90.2%

1-bromo-2-(dilfluoromethoxy)benzene (175278-33-8) + bis(pinacol)diborane (73183-34-3) → 2-(2-(difluoromethoxy)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (960067-33-8)

Guidance literature:

With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; potassium acetate; In 1,4-dioxane; at 85 ℃; for 16h; Inert atmosphere;

Reference yield:

1-bromo-2-(dilfluoromethoxy)benzene (175278-33-8) + 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane (25015-63-8) → 2-(2-(difluoromethoxy)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (960067-33-8)

Guidance literature:

With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; dichloro bis(acetonitrile) palladium(II); triethylamine; at 110 ℃; for 3h; Sealed tube; Inert atmosphere;

DOI:10.1016/j.ejmech.2016.08.068

Reference yield:

2-hydroxybromobenzene (95-56-7) → 2-(2-(difluoromethoxy)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (960067-33-8)

Guidance literature:

Multi-step reaction with 2 steps

1: caesium carbonate / N,N-dimethyl-formamide / 3 h / 105 °C / Inert atmosphere

2: potassium acetate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / 1,4-dioxane / 1.5 h / 100 °C / Inert atmosphere

With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate; caesium carbonate; In 1,4-dioxane; N,N-dimethyl-formamide;

upstream raw materials:

1-bromo-2-(dilfluoromethoxy)benzene

bis(pinacol)diborane

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

2-hydroxybromobenzene

Downstream raw materials:

N-{6-amino-5-[2-(difluoromethoxy)phenyl]pyridin-2-yl}-1-methyl-1H-pyrazole-5-carboxamide

Refernces

• 1、 -. "FUSED RING PYRIMIDINE COMPOUND, INTERMEDIATE, AND PREPARATION METHOD, COMPOSITION AND USE THEREOF". Paragraph 0216-0217. . Retrieved 2018/08/12.
• 2、 -. "PYRIDINE DERIVATIVES". Page/Page column 156; 157. . Retrieved 2009/01/20.