2-Trifluoromethylphenylboronic acid Chemical Properties

Melting point:

111-114 °C (lit.)

Boiling point:

274.5±50.0 °C(Predicted)

Density 

1.36±0.1 g/cm3(Predicted)

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

solubility 

slightly sol. in Methanol

form 

powder to crystal

pka

8.11±0.58(Predicted)

color 

White to Almost white

BRN 

2974465

InChI

InChI=1S/C7H6BF3O2/c9-7(10,11)5-3-1-2-4-6(5)8(12)13/h1-4,12-13H

InChIKey

JNSBEPKGFVENFS-UHFFFAOYSA-N

SMILES

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

CAS DataBase Reference

1423-27-4(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

37/39-26-36

WGK Germany 

3

HazardClass 

IRRITANT

HS Code 

29163990

MSDS

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

2-Trifluoromethylphenylboronic acid Usage And Synthesis

Chemical Properties

white to light beige crystalline powder

Uses

suzuki reaction

Uses

2-Trifluoromethylphenylboronic Acid is a reagent in the preparation of potent inhibitors of human uric acid transporter 1 (hURAT1).

Uses

2-(Trifluoromethyl)phenylboronic acid can be used as a reactant:

• In Suzuki-coupling reactions to prepare 2-trifluoromethyl aryl or heteroaryl derivatives.
• To synthesize 4-(2-trifluoromethyl)phenylpyrrolo[2,3-d]pyrimidine as a potential antagonist of corticotropin-releasing hormone.
• To prepare 2-nitro-6-(trifluoromethyl)phenylboronic acid by nitration reaction.

Synthesis

To a 250-mL three-necked reaction flask, 2.3 g of magnesium flakes were added and heated to dryness under a nitrogen atmosphere. Subsequently, 0.1 g of iodine, 12.8 g of bis(dimethylamino)chloroborane and 30 mL of tetrahydrofuran were added sequentially. A mixed solution consisting of 2.4 g of 2-chloro(trifluoromethyl)benzene and 20 ml of tetrahydrofuran was added slowly dropwise, and stirring was continued for 30 minutes after completion of the addition. Next, a solution consisting of 12.0 g of 2-chloro(trifluoromethyl)benzene and 100 ml of tetrahydrofuran was added slowly and the temperature of the reaction was maintained at 20-30°C. The addition process was completed in about 2 hours. After completion of the reaction, the mixed solution was cooled to 0°C and 50 ml of saturated ammonium chloride solution was added with continuous stirring for 1 hour. After standing and layering, the aqueous phase was extracted with 70 ml of ethyl acetate. The organic layers were combined, dried with magnesium sulfate and concentrated under reduced pressure. The concentrated residue was dissolved in 80 ml of hot ethyl acetate at 65°C and subsequently cooled to room temperature within 2 hours. 300 ml of n-hexane was added and stirring was continued for 3 h. Filtration gave 7.9 g of white solid 2-trifluoromethylphenylboronic acid in 52% yield.

References

[1] Patent: CN104311587, 2017, B. Location in patent: Paragraph 0068; 0069; 0070

2-Trifluoromethylphenylboronic acid(1423-27-4)Related Product Information

• 5-Methyl-1H-benzotriazole
• (Trifluoromethyl)trimethylsilane
• 4-Bromobenzotrifluoride
• 2-(Trifluoromethyl)benzoic acid
• Ethyl 2-(Chlorosulfonyl)acetate
• 3,5-Dimethylphenylboronic acid
• Folic acid
• 4-Aminobenzotrifluoride
• Phenylboronic acid
• 4-Tolylboronic acid
• 4-(Trifluoromethyl)benzaldehyde
• Benzotrifluoride
• Lithium trifluoromethanesulfonate
• Citric acid
• Ascoric Acid
• 2-(TRIFLUOROMETHOXY)BENZALDEHYDE
• alpha,alpha,alpha-Trifluoro-o-cresol
• METHYL 2-(TRIFLUOROMETHOXY)BENZOATE