2-AMINO-4-CHLOROPHENYL BORONIC ACID PINACOL ESTER

Base Information

• Chemical Name: 2-AMINO-4-CHLOROPHENYL BORONIC ACID PINACOL ESTER
• CAS No.: 863578-21-6
• Molecular Formula: C12H17 B Cl N O2
• Molecular Weight: 253.536
• Hs Code.: 2934999090
• Mol file: 863578-21-6.mol

Synonyms:5-Chloro-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline

Chemical Property of 2-AMINO-4-CHLOROPHENYL BORONIC ACID PINACOL ESTER

Chemical Property:

• Boiling Point: 363.6±32.0 °C(Predicted)
• PKA: 2.84±0.11(Predicted)
• PSA: 44.48000
• Density: 1.15±0.1 g/cm3(Predicted)
• LogP: 2.80260
• Storage Temp.: Room temperature.

Purity/Quality:

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

2-Amino-4-chlorophenylboronicacidpinacolester ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 2-AMINO-4-CHLOROPHENYL BORONIC ACID PINACOL ESTER

There total 12 articles about 2-AMINO-4-CHLOROPHENYL 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: 100.0%

2-bromo-5-chloroaniline (823-57-4) + bis(pinacol)diborane (73183-34-3) → 5-chloro-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2yl)benzenamine (863578-21-6)

Guidance literature:

With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; potassium acetate; In dimethyl sulfoxide; at 85 ℃; for 2.5h;

Reference yield: 96.0%

2-bromo-5-chloroaniline (823-57-4) → 5-chloro-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2yl)benzenamine (863578-21-6)

Guidance literature:

With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; potassium acetate; bis(pinacol)diborane; In dimethyl sulfoxide; at 85 ℃; Inert atmosphere;

Reference yield: 73.0%

2-bromo-5-chloroaniline (823-57-4) + 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane (25015-63-8) → 5-chloro-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2yl)benzenamine (863578-21-6)

Guidance literature:

With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; triethylamine; In 1,4-dioxane; at 100 ℃; for 12h; Inert atmosphere;

DOI:10.1021/jacs.9b13599 DOI:10.1021/acs.orglett.0c03497

upstream raw materials:

2-bromo-5-chloroaniline

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

3-chloro-aniline

bis(pinacol)diborane

Refernces

• 1、 Deng, Tianning,Shi, Emily,Thomas, Elana,Driver, Tom G.. "I(III)-catalyzed oxidative cyclization - Migration tandem reactions of unactivated anilines". supporting information. p. 9102 - 9106. Retrieved 2020/11/13.
• 2、 Welsch, Matthew E.,Zhou, Jian,Gao, Yueqiang,Yan, Yunqing,Porter, Gene,Agnihotri, Gautam,Li, Yingjie,Lu, Henry,Chen, Zhongguo,Thomas, Stephen B.. "Discovery of Potent and Selective Leads against Toxoplasma gondii Dihydrofolate Reductase via Structure-Based Design". supporting information. p. 1124 - 1129. Retrieved 2016/12/16.