4-Amino-2-fluorophenylboronic acid, pinacol ester

Base Information

• Chemical Name: 4-Amino-2-fluorophenylboronic acid, pinacol ester
• CAS No.: 819057-45-9
• Molecular Formula: C12H17 B F N O2
• Molecular Weight: 237.082
• Hs Code.: 2931900090
• Mol file: 819057-45-9.mol

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

Chemical Property of 4-Amino-2-fluorophenylboronic acid, pinacol ester

Chemical Property:

• Vapor Pressure: 6.99E-05mmHg at 25°C
• Refractive Index: 1.504
• Boiling Point: 343.6°C at 760 mmHg
• PKA: 3.22±0.10(Predicted)
• Flash Point: 161.6°C
• PSA: 44.48000
• Density: 1.11g/cm³
• LogP: 2.28830
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C

Purity/Quality:

98% ^*data from raw suppliers

4-Amino-2-fluorobenzeneboronic acid, pinacol ester ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 4-Amino-2-fluorophenylboronic acid, pinacol ester

There total 5 articles about 4-Amino-2-fluorophenylboronic 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: 77.0%

3-fluoro-4-bromophenylamine (656-65-5) + bis(pinacol)diborane (73183-34-3) → 3-fluoro-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenylamine (819057-45-9)

Guidance literature:

With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate; In 1,4-dioxane; at 90 ℃; for 12h; Inert atmosphere;

DOI:10.1016/j.ejmech.2021.113497

Reference yield: 73.0%

2-(2-fluoro-4-nitrophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (1073353-89-5) → 3-fluoro-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenylamine (819057-45-9)

Guidance literature:

With 5%-palladium/activated carbon; hydrogen; In methanol; at 20 ℃; for 4h; under 760.051 Torr;

DOI:10.1021/jo402618r

Reference yield:

bis(pinacol)diborane (73183-34-3) → 3-fluoro-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenylamine (819057-45-9)

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:

3-fluoro-4-bromophenylamine

bis(pinacol)diborane

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

2-fluoro-4-nitroaniline

Downstream raw materials:

8-(4-amino-2-fluorophenyl)-2-morpholin-4-yl-benzo[e][1,3]oxazin-4-one

phenyl (3-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)carbamate

1-cyclopropyl-3-(3-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)urea

1-(3-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-3-(2-hydroxyethyl)urea