4-Fluoro-2-methylphenylboronic acid Chemical Properties

Melting point:

191-196 °C(lit.)

Boiling point:

277.4±50.0 °C(Predicted)

Density 

1.20±0.1 g/cm3(Predicted)

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

solubility 

Chloroform (Slightly, Sonicated), DMSO (Slightly), Methanol (Slightly)

pka

8.75±0.58(Predicted)

form 

Powder

color 

White to off-white

InChI

InChI=1S/C7H8BFO2/c1-5-4-6(9)2-3-7(5)8(10)11/h2-4,10-11H,1H3

InChIKey

IQMLIVUHMSIOQP-UHFFFAOYSA-N

SMILES

B(C1=CC=C(F)C=C1C)(O)O

CAS DataBase Reference

139911-29-8(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

37/39-26-36/37/39-27

WGK Germany 

3

HazardClass 

IRRITANT

HS Code 

29163990

MSDS

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

4-Fluoro-2-methylphenylboronic acid Usage And Synthesis

Chemical Properties

white to off-white powder

Uses

suzuki reaction

Synthesis

The general procedure for the synthesis of 4-fluoro-2-methylphenylboronic acid from triisopropyl borate and 2-bromo-5-fluorotoluene was carried out as follows: 2-bromo-5-fluorotoluene (250 g) was dissolved in a solvent mixture of tetrahydrofuran (250 ml) and n-hexane (250 ml) under dry conditions, and cooled to -78 °C. At this temperature, n-butyllithium (991.5 ml) was slowly added dropwise and the reaction temperature was maintained in an ice bath. After the dropwise addition, the reaction mixture was stirred for 1 hour. Subsequently, triisopropyl borate (373.11 g) was added dropwise and stirring was continued at -78°C for 1 hour. After completion of the reaction, the reaction mixture was diluted with aqueous sodium hydroxide solution and then washed with n-heptane. The pH of the aqueous layer was adjusted to 2-3 with hydrochloric acid followed by extraction with ethyl acetate. The organic layers were combined and concentrated under vacuum. The concentrated product was dissolved in ethyl acetate at about 40 °C and n-heptane was added to promote crystallization, resulting in 4-fluoro-2-methylphenylboronic acid. The yield was 61.5% and the HPLC purity was 99.00%.

References

[1] Patent: WO2017/125835, 2017, A1. Location in patent: Paragraph 00117

4-Fluoro-2-methylphenylboronic acid(139911-29-8)Related Product Information

• 3-Cyanophenylboronic acid
• 2-BORONO-5-FLUOROBENZOIC ACID
• 4-FLUORO-2-(TRIFLUOROMETHYL)BENZENEBORONIC ACID
• Tavaborole
• 5-FLUORO-2-METHYLPHENYLBORONIC ACID
• 2-(N-Boc-aminomethyl)-4-fluorophenylboronic acid
• 2-AMINOMETHYL-4-FLUOROPHENYLBORONIC ACID, HCL
• 2-Bromomethyl-4-fluorophenylboronic acid pinacol ester
• 4-Fluoro-2-methylphenylboronic acid
• 2-Bromomethyl-4-fluorophenylboronic acid neopentyl glycol ester
• 4-Fluoro-2-methoxycarbonylphenylboronic acid
• (2-BROMOMETHYL-4-FLUOROBENZENE)BORONIC ACID
• 2-CHLORO-6-FLUORO-3-METHYLPHENYLBORONIC&
• 2-Bromo-3-fluoro-6-methylphenylboronicacid
• 2-FLUORO-4-METHYLPHENYLBORONIC ACID,2-Fluoro-4-methylphenylboronic acid ,97%,2-Fluoro-4-methylphenylboronic Acid (contains varying amounts of Anhydride)
• 3-FLUORO-5-METHYLPHENYLBORONIC ACID
• 6-Bromo-2-fluoro-3-methylphenylboronic acid
• 2-CHLORO-6-FLUORO-5-METHYLPHENYLBORONIC ACID