5-CHLORO-2-FLUOROPHENYLBORONIC ACID Chemical Properties

Melting point:

122-127 °C (lit.)

Boiling point:

310.8±52.0 °C(Predicted)

Density 

1.41±0.1 g/cm3(Predicted)

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

form 

powder to crystal

pka

7.35±0.58(Predicted)

color 

White to Almost white

InChI

1S/C6H5BClFO2/c8-4-1-2-6(9)5(3-4)7(10)11/h1-3,10-11H

InChIKey

GGTUVWGMCFXUAS-UHFFFAOYSA-N

SMILES

OB(O)c1cc(Cl)ccc1F

CAS DataBase Reference

352535-83-2(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-37-60

WGK Germany 

3

HazardClass 

IRRITANT

HS Code 

29319090

Storage Class

11 - Combustible Solids

Hazard Classifications

Acute Tox. 4 Oral

MSDS

• Language:English Provider:SigmaAldrich

5-CHLORO-2-FLUOROPHENYLBORONIC ACID Usage And Synthesis

Uses

suzuki reaction

Uses

Reactant involved in:

• Suzuki cross-coupling reactions
• Synthesis of biaryl amides with muscarinic acetylcholine receptor subtype M1 agonistic activity
• Synthesis of kinesin spindle protein inhibitors
• GABA α2/3 agonist preparation

Synthesis

To a solution of 2-bromo-4-chloro-1-fluorobenzene (5 g, 0.0238 mol) in anhydrous ether (30 ) at -70??C under nitrogen atmosphere was added a 2M solution of n-BuLi in hexane (13 mL, 0.0262 mol). mL) in anhydrous ether (30 ) was added to a 2 M solution of n-BuLi in hexane (13 mL, 0.0262 mol). The solution was stirred at the same temperature for 30 min and then triisopropyl borate (4.93 g,0.0262 mol) was added dropwise to the solution. The white slurry formed was stirred at -70 ??C for 30 min and then warmed to room temperature and stirred for 1 h. The reaction was monitored by TLC and H NMR to monitor the reaction. After the reaction was completed, the reaction mixture was hydrolyzed with 6N NaOH and stirred for 1 h. The reaction mixture was extracted with EtOAc. The organic layer was washed with brine and concentrated under reduced pressure to obtain a viscous compound, which was ground with n-pentane and dried to obtain 5-chloro-2-fluorophenylboronic acid as an off-white solid.

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