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

Base Information

• Chemical Name: 2-chloro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol
• CAS No.: 1443151-85-6
• Molecular Formula: C₁₂H₁₆BClO₃
• Molecular Weight: 254.521
• Mol file: 1443151-85-6.mol

Synonyms:2-chloro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol

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

Chemical Property:

• Boiling Point: 350.5±32.0 °C(Predicted)
• PKA: 8.54±0.10(Predicted)
• Density: 1.19±0.1 g/cm3(Predicted)

Purity/Quality:

99% ^*data from raw suppliers

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

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 4 articles about 2-chloro-5-(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:

5-bromo-2-chlorophenol (183802-98-4) + bis(pinacol)diborane (73183-34-3) → 2-chloro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol (1443151-85-6)

Guidance literature:

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium acetate; In N,N-dimethyl-formamide; for 2h; Reflux;

Reference yield:

3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol (214360-76-6) → 2-chloro-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol (1151564-17-8) + 2-chloro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol (1443151-85-6)

Guidance literature:

With 1,3-dichloro-5,5-dimethylhydantoin; diisopropylamine hydrochloride; In toluene; at 0 ℃; for 4h; Overall yield = 64 %; regioselective reaction; Darkness;

DOI:10.1021/acscatal.8b00327

Reference yield:

tetrabutylammonium 2‐chlorophenyl sulfate + bis(pinacol)diborane (73183-34-3) → 2‐chloro‐4‐(4,4,5,5‐tetramethyl‐1,3,2‐dioxaborolan‐2‐yl)phenol (629658-06-6) + 2-chloro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol (1443151-85-6)

Guidance literature:

tetrabutylammonium 2‐chlorophenyl sulfate; bis(pinacol)diborane; With (1,5-cyclooctadiene)(methoxy)iridium(I) dimer; 4,4'-Dimethoxy-2,2'-bipyridin; In 1,4-dioxane; at 40 ℃; for 14h; Glovebox;

With hydrogenchloride; In 1,4-dioxane; water; for 1h; pH=1 - 2; regioselective reaction; Glovebox;

DOI:10.1021/jacs.9b08464

upstream raw materials:

5-bromo-2-chlorophenol

bis(pinacol)diborane

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

2-monochlorophenol

Downstream raw materials:

ethyl [2-chloro-5-(4-{[2-(4-fluorophenyl)ethyl]amino}-6-methoxy-1,3,5-triazin-2-yl)phenoxy]acetate

[2-chloro-5-(4-{[2-(4-fluorophenyl)ethyl]amino}-6-methoxy-1,3,5-triazin-2-yl)phenoxy]acetic acid

2-[2-chloro-5-(4-{[2-(4-fluorophenyl)ethyl]amino}-6-methoxy-1,3,5-triazin-2-yl)phenoxy]acetamide

2-chloro-5-(4-{[2-(4-fluorophenyl)ethyl]amino}-6-methoxy-1,3,5-triazin-2-yl)phenol