3-AMINO-4-CHLOROPHENYLBORONIC ACID, PINACOL ESTER

Base Information

• Chemical Name: 3-AMINO-4-CHLOROPHENYLBORONIC ACID, PINACOL ESTER
• CAS No.: 850567-56-5
• Molecular Formula: C12H17BClNO2
• Molecular Weight: 253.536
• Hs Code.: 2934999090
• Mol file: 850567-56-5.mol

Synonyms:2-Chloro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline;3-Amino-4-chlorophenylboronic acid, pinacol ester;

Chemical Property of 3-AMINO-4-CHLOROPHENYLBORONIC ACID, PINACOL ESTER

Chemical Property:

• Vapor Pressure: 2.06E-05mmHg at 25°C
• Melting Point: 142-144 ºC
• Refractive Index: 1.53
• Boiling Point: 361.5°C at 760 mmHg
• Flash Point: 172.4°C
• PSA: 44.48000
• Density: 1.15 g/cm³
• LogP: 2.80260
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C

Purity/Quality:

98%min ^*data from raw suppliers

3-Amino-4-chlorophenylboronicacid,pinacolester ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 3-AMINO-4-CHLOROPHENYLBORONIC ACID, PINACOL ESTER

There total 3 articles about 3-AMINO-4-CHLOROPHENYLBORONIC 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: 94.0%

2-(4-Chloro-3-nitrophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (913836-26-7) → 2-chloro-5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)phenylamine (850567-56-5)

Guidance literature:

With iron; ammonium chloride; In ethanol; water; at 105 ℃; for 2h; Temperature;

Reference yield:

o-chloroaniline (95-51-2) + bis(pinacol)diborane (73183-34-3) → 2‐chloro‐4‐(4,4,5,5‐tetramethyl‐1,3,2‐dioxaborolan‐2‐yl)aniline (721960-43-6) + 2-chloro-5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)phenylamine (850567-56-5)

Guidance literature:

With (1,5-cyclooctadiene)(methoxy)iridium(I) dimer; 4,4'-di-tert-butyl-2,2'-bipyridine; In 1,4-dioxane; at 70 ℃; for 16h; Overall yield = 78 percent; Overall yield = 198 mg; Inert atmosphere;

DOI:10.1021/jacs.9b07267

Reference yield:

bis(pinacol)diborane (73183-34-3) → 2-chloro-5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)phenylamine (850567-56-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 2-(4-biphenylyl)-5-phenyloxazole; tert.-butylnitrite / acetonitrile / 4 h / 20 °C

2: 5%-palladium/activated carbon; hydrogen / methanol / 4 h / 20 °C / 760.05 Torr

With tert.-butylnitrite; 5%-palladium/activated carbon; 2-(4-biphenylyl)-5-phenyloxazole; hydrogen; In methanol; acetonitrile;

DOI:10.1021/jo402618r

upstream raw materials:

bis(pinacol)diborane

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

o-chloroaniline

Downstream raw materials:

2,2′-(4-chloro-1,3-phenylene)bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolane)

(2-chloro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)trimethylstannane

2-chloro-4-(pyrazin-2-yl)aniline

2-chloro-4-(pyrimidin-5-yl)aniline

Refernces

• 1、 -. "A 3 - amino - 4 - chlorophenyl boronic acid [...] alcohol ester synthesis method (by machine translation)". Paragraph 0005; 0008-0010. . Retrieved 2018/03/01.