3-Amino-2-methylphenylboronic acid, pinacol ester

Base Information

• Chemical Name: 3-Amino-2-methylphenylboronic acid, pinacol ester
• CAS No.: 882678-96-8
• Molecular Formula: C13H20 B N O2
• Molecular Weight: 233.118
• Hs Code.: 2934999090
• Mol file: 882678-96-8.mol

Synonyms:2-Methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline;[2-Methyl-3-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)phenyl]amine

Chemical Property of 3-Amino-2-methylphenylboronic acid, pinacol ester

Chemical Property:

• Vapor Pressure: 1.59E-05mmHg at 25°C
• Refractive Index: 1.515
• Boiling Point: 365.3°C at 760 mmHg
• PKA: 4.44±0.10(Predicted)
• Flash Point: 174.7°C
• PSA: 44.48000
• Density: 1.03g/cm³
• LogP: 2.45760

Purity/Quality:

≥99.0% ^*data from raw suppliers

3-Amino-2-methylphenylboronic acid pinacol ester ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 22

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 3-Amino-2-methylphenylboronic acid, pinacol ester

There total 9 articles about 3-Amino-2-methylphenylboronic 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-(2-methyl-3-nitrophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (910235-64-2) → 2-methyl-3-( 4,4,5,5-tetramethyl[1,3,2]dioxaborolane-2-yl)phenylamine (882678-96-8)

Guidance literature:

With hydrogen; palladium 10% on activated carbon; In methanol; at 20 ℃; for 13h;

Reference yield: 91.0%

3-bromo-2-methylaniline (55289-36-6) + bis(pinacol)diborane (73183-34-3) → 2-methyl-3-( 4,4,5,5-tetramethyl[1,3,2]dioxaborolane-2-yl)phenylamine (882678-96-8)

Guidance literature:

With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; potassium acetate; In 1,4-dioxane; at 110 ℃; for 2.75h; Inert atmosphere;

DOI:10.1021/acs.jmedchem.9b00167 DOI:10.1021/acs.jmedchem.9b00167

Reference yield: 85.0%

3-bromo-2-methylaniline (55289-36-6) + 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane (25015-63-8) → 2-methyl-3-( 4,4,5,5-tetramethyl[1,3,2]dioxaborolane-2-yl)phenylamine (882678-96-8)

Guidance literature:

With palladium diacetate; triethylamine; CyJohnPhos; In 1,4-dioxane; at 80 ℃; for 1h;

DOI:10.1021/jm800295d

upstream raw materials:

3-iodo-2-methylphenylamine

bis(pinacol)diborane

2-(2-methyl-3-nitrophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

3-bromo-2-methylaniline

Downstream raw materials:

N-(2-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-3-(trifluoromethyl)benzamide

N-(2-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-4,5,6,7-tetrahydrobenzo[b]thiophene-2-carboxamide

4-tert-butyl-N-[2-methyl-3-(4,4,5,5-tetramethyl-[1,2,3]dioxaborolan-2-yl)-phenyl]-benzamide

2-methyl-3-(4-morpholin-4-yl-thieno[3,2-d]pyrimidin-2-yl)phenylamine

Refernces

• 1、 Liu, Mei,Zhang, Yu,Guo, Yu,Gao, Jian,Huang, Wenhai,Dong, Xiaowu. "A comparative study of the recent most potent small-molecule PD-L1 inhibitors: what can we learn?". . p. 1230 - 1239. Retrieved 2021/04/26.
• 2、 -. "BIARYL DERIVATIVE, PREPARATION METHOD THEREOF AND PHARMACEUTICAL APPLICATION THEREOF". Paragraph 0100; 0101. . Retrieved 2020/12/22.