3,4-Dichlorophenylboronic acid Chemical Properties

Melting point:

280-285 °C (lit.)

Boiling point:

339.2±52.0 °C(Predicted)

Density 

1.47±0.1 g/cm3(Predicted)

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

solubility 

Acetone (Slightly), Chloroform (Very Slightly, Heated, Sonicated)

pka

7.37±0.10(Predicted)

form 

Powder

color 

White to off-white

BRN 

7369790

InChI

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

InChIKey

JKIGHOARKAIPJI-UHFFFAOYSA-N

SMILES

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

CAS DataBase Reference

151169-75-4(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi,F

Risk Statements 

36/37/38-19-11

Safety Statements 

26-36-37/39-33-16

WGK Germany 

3

HazardClass 

IRRITANT

HS Code 

29163990

MSDS

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

3,4-Dichlorophenylboronic acid Usage And Synthesis

Chemical Properties

white to off-white powder

Uses

suzuki reaction

Uses

3,4-Dichlorophenylboronic Acid is a reactant used in the synthesis of 2-(3-fluoro-4-methylsulfonylaminophenyl)propanamides as hTRPV1 antagonists.

Synthesis

GENERAL PROCEDURE: A 1 M solution (375 μL, 375 μmol) of phenylmagnesium bromide (PhMgBr) THF (375 μL, 375 μmol) was added dropwise to a solution of diisopropylaminoborane (DIPAB, 863 mg, 7.5 mmol) and magnesium shavings (182 mg, 7.5 mmol) in tetrahydrofuran (THF, 4 mL) under nitrogen protection at room temperature. After 10 min of reaction, 30 mL of anhydrous THF was added, followed by 4-bromo-1,2-dichlorobenzene (5 mmol). The reaction mixture was cooled to 0 °C and quenched by slow addition of methanol (7 mL). After 1 h of reaction, the volatile solvent was removed by distillation under reduced pressure and the resulting solid was dissolved in a 1 N hydrochloric acid/methanol (7:3, v/v) mixture. After stirring at room temperature for 1 h, ethyl acetate (100 mL) was added for extraction, and the organic phase was washed sequentially with 1 N hydrochloric acid (30 mL) and saturated saline (3 x 30 mL). The organic phase was concentrated under reduced pressure to give the crude product, which was purified by recrystallization from water (H2O) to give the target product 3,4-dichlorophenylboronic acid.

References

[1] Tetrahedron, 2019, vol. 75, # 2, p. 164 - 171

3,4-Dichlorophenylboronic acid(151169-75-4)Related Product Information

• Permethrin
• 2,4-Dichlorobenzyl chloride
• Phenylboronic acid
• 1,3-Dichlorobenzene
• 4-Chlorophenylboronic acid
• 1,2-Dichlorobenzene
• Lobenzarit disodium
• 3,4-Difluorophenylboronic acid
• 2,4,5-Trichlorophenylboronic acid
• 2,3,4-Trichlorophenylboronic acid
• 3,4-DICHLOROPHENYLBORONIC ACID, PINACOL ESTER
• 2,5-Dichlorophenylboronic Acid (contains varying amounts of Anhydride),2,5-Dichlorophenylboronic acid ,98%,2,5-DICHLOROPHENYLBORONIC ACID
• (3,4,5-Trichlorophenyl)boronic acid
• 3,5-Dichlorophenylboronic acid
• 2,4-DICHLOROPHENYLBORONIC ACID, PINACOL ESTER
• 2,6-DICHLOROPHENYLBORONIC ACID
• 3,5-DICHLOROPHENYLBORONIC ACID, PINACOL ESTER
• p-Dichlorobenzene