3-Fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol

Base Information

• Chemical Name: 3-Fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol
• CAS No.: 1029439-02-8
• Molecular Formula: C12H16BFO3
• Molecular Weight: 238.067
• Hs Code.: 2934999090
• Mol file: 1029439-02-8.mol

Synonyms:3-Fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol;2-Fluoro-4-hydroxybenzeneboronic acid pinacol ester, 96%;2-FLUORO-4-HYDROXYPHENYLBORONIC ACID, PINACOL ESTER

Chemical Property of 3-Fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol

Chemical Property:

• Melting Point: 110-112℃
• Boiling Point: 338.8±32.0 °C(Predicted)
• PKA: 8.66±0.35(Predicted)
• PSA: 38.69000
• Density: 1.15±0.1 g/cm3(Predicted)
• LogP: 1.83050
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C

Purity/Quality:

97% ^*data from raw suppliers

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

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 3-Fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol

There total 4 articles about 3-Fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol 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: 97.5%

4-bromo-3-fluorophenol (121219-03-2) + bis(pinacol)diborane (73183-34-3) → 3-fluoro-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenol (1029439-02-8)

Guidance literature:

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium acetate; In 1,4-dioxane; at 95 ℃; for 4h;

Reference yield: 66.0%

→ 3-fluoro-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenol (1029439-02-8)

Guidance literature:

With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate; In N,N-dimethyl-formamide; for 16h; Inert atmosphere; Reflux;

Reference yield:

tetrapropylammonium 3-fluorophenylsulfate + bis(pinacol)diborane (73183-34-3) → 3-fluoro-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenol (1029439-02-8) + 3-fluoro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol

Guidance literature:

tetrapropylammonium 3-fluorophenylsulfate; bis(pinacol)diborane; With (1,5-cyclooctadiene)(methoxy)iridium(I) dimer; 4,4'-Dimethoxy-2,2'-bipyridin; In 1,4-dioxane; at 60 ℃; for 20h; Glovebox;

With hydrogenchloride; In 1,4-dioxane; water; for 1h; pH=1 - 2; Overall yield = 73 percent; Overall yield = 87 mg; regioselective reaction; Glovebox;

DOI:10.1021/jacs.9b08464

upstream raw materials:

4-bromo-3-fluorophenol

bis(pinacol)diborane

3-fluorophenol

Downstream raw materials:

(R)-(4-(6-amino-5-(1-(2,6-dichloro-3-fluorophenyl)-ethoxy)pyridin-3-yl)-3-fluorophenyl)dimethylphosphine oxide