(4-CHLORO-3-HYDROXYPHENYL)BORONIC ACID

Base Information

• Chemical Name: (4-CHLORO-3-HYDROXYPHENYL)BORONIC ACID
• CAS No.: 915201-06-8
• Molecular Formula: C6H6BClO3
• Molecular Weight: 172.376
• Hs Code.: 2931900090
• Mol file: 915201-06-8.mol

Synonyms:4-Chloro-3-hydroxyphenylboronic acid;3-hydroxy-4-chlorophenylboronic acid;

Chemical Property of (4-CHLORO-3-HYDROXYPHENYL)BORONIC ACID

Chemical Property:

• Melting Point: >250 °C
• Boiling Point: 359.9±52.0 °C(Predicted)
• PKA: 8.07±0.10(Predicted)
• PSA: 60.69000
• Density: 1.49±0.1 g/cm3(Predicted)
• LogP: -0.27460
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C

Purity/Quality:

98%min ^*data from raw suppliers

4-Chloro-3-hydroxyphenylboronicacid ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: 4-Chloro-3-hydroxyphenylboronic acid

Technology Process of (4-CHLORO-3-HYDROXYPHENYL)BORONIC ACID

There total 3 articles about (4-CHLORO-3-HYDROXYPHENYL)BORONIC ACID 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: 25.0%

5-bromo-2-chlorophenol (183802-98-4) → (4-chloro-3-hydroxyphenyl)boronic acid (915201-06-8)

Guidance literature:

5-bromo-2-chlorophenol; With n-butyllithium; In tetrahydrofuran; at -78 ℃; for 1.5h; Inert atmosphere;

With Triisopropyl borate; In tetrahydrofuran; at -78 ℃; Inert atmosphere;

With hydrogenchloride; water; at 0 ℃;

DOI:10.1021/jm901705h

Reference yield:

(4-chloro-3-methoxyphenyl)boronic acid (89694-47-3) → (4-chloro-3-hydroxyphenyl)boronic acid (915201-06-8)

Guidance literature:

With boron tribromide; In dichloromethane; at 0 - 20 ℃; for 16h;

Reference yield:

5-Bromo-2-chloroanisole (16817-43-9) → (4-chloro-3-hydroxyphenyl)boronic acid (915201-06-8)

Guidance literature:

Multi-step reaction with 2 steps

1.1: n-butyllithium / diethyl ether; hexane / 0.5 h / -78 °C

1.2: 1 h / -78 - 20 °C

1.3: 1 h / 0 °C

2.1: boron tribromide / dichloromethane / 16 h / 0 - 20 °C

With n-butyllithium; boron tribromide; In diethyl ether; hexane; dichloromethane;

upstream raw materials:

5-bromo-2-chlorophenol

5-Bromo-2-chloroanisole

(4-chloro-3-methoxyphenyl)boronic acid

Downstream raw materials:

((2R,3S,6S)-3-acetoxy-6-(4-chloro-3-hydroxyphenyl)-3,6-dihydro-2H-pyran-2-yl)methyl acetate

(2R,3S,4R,5S,6R)-2-(4-chloro-3-hydroxyphenyl)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol

((2R,3S,4R,5S,6R)-3-acetoxy-6-(4-chloro-3-hydroxyphenyl)-4,5-dihydroxytetrahydro-2H-pyran-2-yl)methyl acetate

Refernces

• 1、 Lawrence Woo,Jackson, Toby,Putey, Aurélien,Cozier, Gyles,Leonard, Philip,Ravi Acharya,Chander, Surinder K.,Purohit, Atul,Reed, Michael J.,Potter, Barry V. L.. "Highly potent first examples of dual aromatase-steroid sulfatase inhibitors based on a biphenyl template". experimental part. p. 2155 - 2170. Retrieved 2010/08/19.