3-Fluoro-4-methoxybenzeneboronic acid Chemical Properties

Melting point:

206-211 °C (lit.)

Boiling point:

318.1±52.0 °C(Predicted)

Density 

1.26±0.1 g/cm3(Predicted)

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

solubility 

soluble in Methanol

form 

powder

pka

7.87±0.10(Predicted)

color 

White to Light yellow to Light orange

BRN 

7370120

CAS DataBase Reference

149507-26-6(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi,Xn

Risk Statements 

36/37/38-20/21/22

Safety Statements 

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

WGK Germany 

3

HazardClass 

IRRITANT

HS Code 

29319090

MSDS

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

3-Fluoro-4-methoxybenzeneboronic acid Usage And Synthesis

Chemical Properties

White solid

Uses

3-Fluoro-4-methoxyphenylboronic Acid is a useful reagent for regioselective Suzuki coupling reactions and other synthetic transformations.

Uses

Reactant for:

• Preparation of hydroxyphenylnaphthols as 17?-hydroxysteroid dehydrogenase Type 2 inhibitors
• Regioselective Suzuki coupling
• Ruthenium-catalyzed arylation reactions
• Synthesis of amino-trimethoxyphenyl-aryl thiazoles as microtubule inhibitors and potential antitumors
• Rhodium catalyzed cyanation
• Petasis reaction

Uses

suzuki reaction

General Description

Contains varying amounts of anhydride

Synthesis

3-Fluoro-4-methoxyphenylboronic acid was synthesized as follows: using 4-bromo-2-fluoroanisole (10 g, 0.049 mol) as starting material, n-butyllithium (23.4 mL of 2.5 M hexane solution, 0.059 mol) was added dropwise under anhydrous and oxygen-free conditions at -78°C and the reaction was stirred for 1 hour. Subsequently, triisopropyl borate (45.2 mL, 36.9 g, 0.196 mol) was slowly added and the reaction mixture was gradually warmed to room temperature and stirring was continued for 12 hours. Upon completion of the reaction, the reaction was quenched by the addition of dilute hydrochloric acid, extracted with ethyl acetate and the organic phase was dried over anhydrous sodium sulfate and concentrated. The crude product was purified by column chromatography to afford 7.1 g of 3-fluoro-4-methoxyphenylboronic acid as white solid in 85.2% yield. The product was confirmed by mass spectrometry (ESI), m/z 169 (MH)-; 1H NMR (DMSO-d6) data were as follows: δ 3.84 (3H, s), 7.10-7.16 (1H, m), 7.51-7.60 (2H, m).

References

[1] Patent: US2003/181519, 2003, A1

3-Fluoro-4-methoxybenzeneboronic acid(149507-26-6)Related Product Information

• 4-Methoxybenzoic acid
• 4-Methoxybenzyl alcohol
• 4-Tolylboronic acid
• p-Anisaldehyde
• 4-(Trifluoromethoxy)aniline
• (4-METHOXYPHENYL)-BORANE
• (Trifluoromethoxy)benzene
• 3-Methoxyacetophenone
• 4-Methoxybenzyl cyanide
• Phenylboronic acid
• 4-Methoxybenzoyl chloride
• 4-Methoxyphenylboronic acid
• Anisole
• Fluorine
• 4-Benzyloxy-2,3-difluorobenzeneboronic acid
• 4-BUTOXY-2,3,5,6-TETRAFLUOROBENZENEBORONIC ACID
• 2,5-DIFLUORO-4-METHOXYPHENYLBORONIC ACID
• 4-(Benzyloxy)-3-fluorophenylboronic acid