2-AMINO-5-FLUOROPHENYL BORONIC ACID PINACOL ESTER

Base Information

• Chemical Name: 2-AMINO-5-FLUOROPHENYL BORONIC ACID PINACOL ESTER
• CAS No.: 863578-24-9
• Molecular Formula: C12H17 B F N O2
• Molecular Weight: 237.082
• Mol file: 863578-24-9.mol

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

Chemical Property of 2-AMINO-5-FLUOROPHENYL BORONIC ACID PINACOL ESTER

Chemical Property:

• Melting Point: 49-50℃
• PSA: 44.48000
• LogP: 2.28830
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C

Purity/Quality:

97% ^*data from raw suppliers

4-Fluoro-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline 95% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: 2-Amino-5-fluorobenzeneboronic acid pinacol ester is used as a pharmaceutical intermediate.

Technology Process of 2-AMINO-5-FLUOROPHENYL BORONIC ACID PINACOL ESTER

There total 5 articles about 2-AMINO-5-FLUOROPHENYL 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: 83.0%

2-bromo-4-fluoroaniline (1003-98-1) + 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane (25015-63-8) → 4-fluoro-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2yl)benzamine (863578-24-9)

Guidance literature:

With bis-triphenylphosphine-palladium(II) chloride; triethylamine; In 1,4-dioxane; at 120 ℃; for 12h; Inert atmosphere;

DOI:10.1021/ol5010615

Reference yield: 60.0%

2-bromo-4-fluoroaniline (1003-98-1) + bis(pinacol)diborane (73183-34-3) → 4-fluoro-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2yl)benzamine (863578-24-9)

Guidance literature:

With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate; In 1,4-dioxane; for 10h; Reflux;

Reference yield:

4-fluoroaniline (371-40-4) → 4-fluoro-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2yl)benzamine (863578-24-9)

Guidance literature:

Multi-step reaction with 3 steps

1: tetrahydrofuran / 1 h / 20 °C / Inert atmosphere; Glovebox

2: (1,5-cyclooctadiene)(methoxy)iridium(I) dimer; N⁴,N⁴,N^4',N^4'-tetramethyl-[2,2'-bipyridine]-4,4'-diamine / tetrahydrofuran / 16 h / 80 °C / Inert atmosphere; Glovebox

3: methanol / tetrahydrofuran / 20 °C / Inert atmosphere; Glovebox

With methanol; (1,5-cyclooctadiene)(methoxy)iridium(I) dimer; N⁴,N⁴,N^4',N^4'-tetramethyl-[2,2'-bipyridine]-4,4'-diamine; In tetrahydrofuran;

DOI:10.1002/anie.201306511

upstream raw materials:

2-bromo-4-fluoroaniline

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

4-fluoroaniline

bis(pinacol)diborane

Downstream raw materials:

methyl 2-(2-amino-5-fluorophenyl)-3-cyclohexyl-1H-indole-6-carboxylate

C₁₁H₉FN₂

1-methyl-2-(2-azido-5-fluorophenyl)pyridinium triflate

2-(2-azido-5-fluorophenyl)pyridine

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