3-Chlorophenylboronic acid Chemical Properties

Melting point:

185-189 °C(lit.)

Boiling point:

311.4±44.0 °C(Predicted)

Density 

1.32±0.1 g/cm3(Predicted)

storage temp. 

Inert atmosphere,Room Temperature

solubility 

soluble in Methanol

pka

7.55±0.10(Predicted)

form 

Crystalline Powder or Needles

color 

White to light yellow-green

Water Solubility 

Slightly soluble in water. soluble in ether, tetrahydrofuran,, dimethyl sulfoxide, dimethyl formamide, methanol.

BRN 

2936343

InChI

InChI=1S/C6H6BClO2/c8-6-3-1-2-5(4-6)7(9)10/h1-4,9-10H

InChIKey

SDEAGACSNFSZCU-UHFFFAOYSA-N

SMILES

B(C1=CC=CC(Cl)=C1)(O)O

CAS DataBase Reference

63503-60-6(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xn,Xi

Risk Statements 

20/21/22-36/37/38

Safety Statements 

36-37/39-26

WGK Germany 

3

HazardClass 

IRRITANT

HS Code 

29163990

MSDS

• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS
• Language:English Provider:ALFA

3-Chlorophenylboronic acid Usage And Synthesis

Chemical Properties

white to light yellow-green crystalline powder

Uses

3-Chlorophenylboronic acid is employed as a reactant involved in 1,4-conjugate addition reactions with ethenesulfonamides to form arylethanesulfonamides, Suzuki-Miyaura reactions with dibromotrifluoromethylbenzene, cross-coupling reactions with diazoesters3 or potassium cyanate. It is involved in the synthesis of biarylketones and phthalides and synthesis of inhibitors including PDE4 inhibitors6 among others.

Uses

suzuki reaction

Uses

Reactant involved in:

• 1,4-conjugate addition reactions with ethenesulfonamides to form arylethanesulfonamides
• Suzuki-Miyaura reactions with dibromotrifluoromethylbenzene
• Cross-coupling reactions with diazoesters or potassium cyanate
• Synthesis of biarylketones and phthalides
• Synthesis of inhibitors including PDE4 inhibitors among others

Synthesis

Using m-dichlorobenzene as the starting material, iodine particles and 1,2-dibromoethane as the initiator reacts with magnesium in an organic solvent to prepare 3-chlorophenyl magnesium chloride. Then, the trimethyl borate is reacted with an organic solvent to prepare 3-chlorophenyl borate dimethyl ester. Finally, the product 3-chlorophenylboronic acid is obtained through hydrolysis, extraction, and crystallization.

Solubility in organics

3-Chlorophenylboronic acid can be dissolved in organic solvents such as N, N-dimethylformamide, ethyl acetate, and dichloromethane. In addition, it also has specific solubility in low-polarity and non-polar organic solvents, but 3-chlorophenylboronic acid has poor solubility in water.

3-Chlorophenylboronic acid(63503-60-6)Related Product Information

• Zinc borate
• 1-Chloro-3-nitrobenzene
• 1,3-Dichlorobenzene
• Phenylboronic acid
• Citric acid
• Chlorphenamine maleate
• Hyaluronic acid
• Ethyl 2-(Chlorosulfonyl)acetate
• Folic acid
• Ascoric Acid
• 3,5-Dichlorophenylboronic acid
• 2,3,4-Trichlorophenylboronic acid
• 4-FLUORO-3-CHLOROPHENYLBORONIC ACID
• 2,3-Dichlorophenylboronic acid
• (3,4,5-Trichlorophenyl)boronic acid
• 3,4-Dichlorophenylboronic acid
• 5-CHLORO-2-METHYLPHENYLBORONIC ACID
• 5-CHLORO-2-ETHOXYPHENYLBORONIC ACID