4-Fluoro-2-methoxyphenylboronic acid Chemical Properties

Melting point:

131-136 °C (lit.)

Boiling point:

294.8±50.0 °C(Predicted)

Density 

1.26±0.1 g/cm3(Predicted)

storage temp. 

Inert atmosphere,Room Temperature

pka

8.69±0.58(Predicted)

form 

Crystalline Powder

color 

White

InChI

InChI=1S/C7H8BFO3/c1-12-7-4-5(9)2-3-6(7)8(10)11/h2-4,10-11H,1H3

InChIKey

ADJBXDCXYMCCAD-UHFFFAOYSA-N

SMILES

B(C1=CC=C(F)C=C1OC)(O)O

CAS DataBase Reference

179899-07-1(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36/37/39-36-60-37

WGK Germany 

3

HazardClass 

IRRITANT

HS Code 

29319090

MSDS

• Language:English Provider:SigmaAldrich

4-Fluoro-2-methoxyphenylboronic acid Usage And Synthesis

Uses

suzuki reaction

Uses

Reactant involved in:
Suzuki-Miyaura cross-coupling reactions for synthesis of heterobiaryls
Suzuki and Still coupling for synthesis of antithrombotic drugs
Reactant / precursor used for the synthesis of biologically active molecules including:
2-(4-pyridyl)thienopyridinones for use as GSK-3β inhibitors
Arylheteroarylmethylamines as NR2B subtype of NMDA receptor antagonists with antidepressant activity
Biphenylketones for use as dual modulators of inflammation and bone loss
CB1 antagonists

Synthesis

4-Fluoro-2-methoxyphenylboronic acid was synthesized as follows: 2-bromo-5-fluoroanisole (5.9 g, 29 mmol) and anhydrous tetrahydrofuran (50 mL) were added to a dry round-bottomed flask under argon protection. After cooling the reaction system to -78°C, n-butyllithium (17.4 mL, 43.5 mmol) was added slowly and dropwise. After stirring the reaction at -78°C for 30 minutes, trimethyl borate (4.9 mL, 43.5 mmol) was added, followed by a slow warming of the reaction mixture to room temperature (~1.3 hours). After completion of the reaction, the mixture was cooled to 0°C and acidified by adding 10% aqueous hydrochloric acid (20 mL). Tetrahydrofuran was removed by distillation under reduced pressure and saturated saline (50 mL) was added. The aqueous phase was extracted twice with ether. The organic phases were combined and washed sequentially with 10% aqueous hydrochloric acid and saturated saline. The organic layer was dried over anhydrous magnesium sulfate and concentrated under reduced pressure to give the yellow solid product 4-fluoro-2-methoxyphenylboronic acid (4 g, 82% yield). The product was characterized by 1H NMR (400 MHz, acetone-d6): δ 7.84 (t, 1H, J = 8 Hz, C6-H), 6.85 (dd, 1H, J = 12.2 Hz, C3-H), 6.76 (td, 1H, J = 8, 2 Hz, C5-H).

References

[1] Patent: US2004/6134, 2004, A1

4-Fluoro-2-methoxyphenylboronic acid(179899-07-1)Related Product Information

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