2,3-Dichlorophenylboronic acid Chemical Properties

Melting point:

125 °C (dec.) (lit.)

Boiling point:

349.8±52.0 °C(Predicted)

Density 

1.47±0.1 g/cm3(Predicted)

storage temp. 

Inert atmosphere,Store in freezer, under -20°C

solubility 

Soluble in methanol.

pka

7.26±0.58(Predicted)

form 

Powder

color 

White

InChI

InChI=1S/C6H5BCl2O2/c8-5-3-1-2-4(6(5)9)7(10)11/h1-3,10-11H

InChIKey

TYIKXPOMOYDGCS-UHFFFAOYSA-N

SMILES

B(C1=CC=CC(Cl)=C1Cl)(O)O

CAS DataBase Reference

151169-74-3(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xn,Xi

Risk Statements 

36/37/38-22

Safety Statements 

37/39-26-36

WGK Germany 

3

HazardClass 

IRRITANT

HS Code 

29319090

MSDS

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

2,3-Dichlorophenylboronic acid Usage And Synthesis

Chemical Properties

white powder

Uses

suzuki reaction

Uses

2,3-Dichlorophenylboronic Acid is used as a reagent in the synthesis of trisubstituted thiazoles as Cdc7 kinase inhibitors. It is also used as a reagent in the synthesis of aminoarylpyridazines as selective CB2 agonists for treatment of inflammatory pain.

Synthesis

1. A solution was prepared by dissolving 1-bromo-2,3-dichlorobenzene (20 g, 0.088 mol, Aldrich) in anhydrous tetrahydrofuran (44.24 ml) under the protection of dry inert gas. 2. The above solution was slowly added dropwise to anhydrous tetrahydrofuran (16 ml) of n-butyllithium (1.6 M in hexane, 66.36 ml, 0.11 mol) solution, with the reaction temperature strictly controlled below -65°C. 3. After the dropwise addition, the light yellow suspension formed was stirred continuously at -78°C for 75 min. 4. Trimethyl borate (13.28 ml, 12.16 g, 0.12 mol) was slowly added while keeping the temperature below -55°C. 5. The reaction mixture was gradually warmed up to room temperature and stirred overnight. 6. Excess n-butyllithium was quenched with water (30 ml) and the reaction mixture was subsequently concentrated under reduced pressure.7. The concentrated residue was suspended in water and acidified with 2M hydrochloric acid (10 ml).8. The insoluble solid was collected by filtration, washed well with water and then dried.9. The dried solid was suspended in petroleum ether at 60-80°C, stirred at room temperature for 10 min, filtered and dried under vacuum.10. Finally, 8.42 g of 2,3-dichlorophenylboronic acid was obtained in 50% yield with a melting point of 235-238 °C.

References

[1] Patent: US6255307, 2001, B1

2,3-Dichlorophenylboronic acid(151169-74-3)Related Product Information

• 1,3-Dichlorobenzene
• 1,2-Dichlorobenzene
• 4-Chlorophenylboronic acid
• Lobenzarit disodium
• Phenylboronic acid
• Folic acid
• Ethyl 2-(Chlorosulfonyl)acetate
• 2,4-Dichlorobenzyl chloride
• Permethrin
• Citric acid
• Ascoric Acid
• p-Dichlorobenzene
• 3-Chlorophenylboronic acid
• 2,3,5-TRICHLOROBENZENEBORONIC ACID
• 2,3,4-Trichlorophenylboronic acid
• 2,4-DICHLOROPHENYLBORONIC ACID, PINACOL ESTER
• 2,6-DICHLOROPHENYLBORONIC ACID
• 3,5-Dichlorophenylboronic acid