2-Fluorophenylboronic acid Chemical Properties

Melting point:

101-110 °C (lit.)

Boiling point:

267.8±42.0 °C(Predicted)

Density 

1.24±0.1 g/cm3(Predicted)

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

solubility 

soluble in Methanol

pka

8.32±0.58(Predicted)

form 

Crystalline Powder

color 

White to light yellow

BRN 

3030413

InChI

InChI=1S/C6H6BFO2/c8-6-4-2-1-3-5(6)7(9)10/h1-4,9-10H

InChIKey

QCSLIRFWJPOENV-UHFFFAOYSA-N

SMILES

B(C1=CC=CC=C1F)(O)O

CAS DataBase Reference

1993-03-9(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xn,Xi

Risk Statements 

36/37/38-22

Safety Statements 

37/39-26-36/37/39-27-24/25

WGK Germany 

3

HazardClass 

IRRITANT

HS Code 

29319090

MSDS

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

2-Fluorophenylboronic acid Usage And Synthesis

Chemical Properties

white to light yellow crystalline powder

Uses

suzuki reaction

Uses

2-Fluorophenylboronic Acid, is used in Rh-catalyzed enantioselective addition reactions, and Rhodium and Palladium-catalyzed substitution reactions. It can also be used in the preparation of phenylboronic catechol esters as promising anion receptors for polymer electrolytes.

Uses

Used for the preparation of biologically active biphenyls and arylboron difluoride Lewis acids.

Synthesis

The general procedure for the synthesis of 2-fluorophenylboronic acid from o-bromofluorobenzene was as follows: 10.0 g (57.1 mmol) of 1-bromo-2-fluorobenzene and anhydrous tetrahydrofuran were added to a reaction flask and the mixture was subsequently cooled to -70 °C. At -70 °C, 44.2 ml (68.5 mmol) of 1.55 M n-butyllithium solution was slowly added dropwise to the reaction mixture. The temperature was maintained at -70 °C and stirring of the reaction mixture was continued for 1.5 hours. Subsequently, 21.5 g (114.2 mmol) of triisopropyl borate was added dropwise and the reaction temperature was gradually raised to room temperature and stirring was continued for 4 hours. Upon completion of the reaction, aqueous hydrochloric acid was added to the reaction mixture and extracted with dichloromethane. The organic phases were combined and the solvent was removed by distillation under reduced pressure to give the crude product of 2-fluorophenylboronic acid. The crude product was purified by column chromatography (eluent: hexane/acetone) to give 4.8 g (yield: 61%) of pure 2-fluorophenylboronic acid.

References

[1] Patent: US2012/273770, 2012, A1. Location in patent: Page/Page column 24
[2] Patent: US2004/6076, 2004, A1. Location in patent: Page 15
[3] Journal of Organic Chemistry, 2013, vol. 78, # 13, p. 6427 - 6439

2-Fluorophenylboronic acid(1993-03-9)Related Product Information

• 2-Fluoropyridine-4-boronic acid
• Phenylboronic acid
• Sodium tetrafluoroborate
• Ammonium fluoborate
• Florfenicol
• Transfluthrin
• 4-Fluorobenzaldehyde
• Zinc borate
• Fluoroboric acid
• Potassium tetrafluoroborate
• 1,2-Difluorobenzene
• Citric acid
• Ascoric Acid
• 3,5-Difluorophenylboronic acid
• Phenylacetone
• FENFLURAMINE
• 4-Fluorophenylboronic acid292,4-Fluorophenylboronic Acid (contains varying amounts of Anhydride)
• 2-ETHOXYPHENYLBORONIC ACID