4-Trifluoromethylphenylboronic acid Chemical Properties

Melting point:

245-250 °C(lit.)

Boiling point:

258.6±50.0 °C(Predicted)

Density 

1.36±0.1 g/cm3(Predicted)

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

solubility 

soluble in Methanol

pka

7.82±0.10(Predicted)

form 

Powder

color 

White

Water Solubility 

Soluble in DMSO, not in water

BRN 

3544189

InChI

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

InChIKey

ALMFIOZYDASRRC-UHFFFAOYSA-N

SMILES

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

CAS DataBase Reference

128796-39-4(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi,Xn

Risk Statements 

36/37/38-22

Safety Statements 

37/39-26-36

WGK Germany 

3

HazardClass 

IRRITANT

HS Code 

29319090

MSDS

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

4-Trifluoromethylphenylboronic acid Usage And Synthesis

Chemical Properties

white powder

Uses

suzuki reaction

Uses

50

Uses

4-(Trifluoromethyl)phenylboronic Acid is a reactant used in the preparation of alkenyl-substituted cyclopenta[b]indole compounds with antitumor activity.

Synthesis

[Example 4] In this embodiment, the synthesis of 9-[4-(carbazol-9-yl)phenyl]-10-(4-trifluoromethylphenyl)anthracene (CF3CzPA) represented by structural formula (42) is described. [Step 1] Synthesis of 9-bromo-10-(4-trifluoromethylphenyl)anthracene (i) Synthesis of 4-(trifluoromethyl)phenylboronic acid The synthesis scheme of 4-(trifluoromethylphenylboronic acid) is shown in (E-1). (1) 33 g (0.15 mol) of p-bromobenzotrifluoride was added to a 500 mL three-necked flask under nitrogen protection. Subsequently, 200 mL of tetrahydrofuran (THF) was added and the mixture was stirred. The mixed solution was cooled to -78 °C and 100 mL (0.16 mol) of n-butyllithium (1.6 mol/L) solution was slowly added dropwise through a dropping funnel. After the dropwise addition was completed, stirring was continued for 1 hour by keeping it at -78°C. Then, 22.3 mL (0.20 mol) of trimethyl borate was added and the reaction mixture was gradually warmed to room temperature and stirred for about 12 hours. After the reaction was completed, 100 mL of dilute hydrochloric acid (1 mol/L) was added to the reaction solution and stirring was continued for 1 hour. The aqueous layer was extracted three times with ethyl acetate, the organic layers were combined, washed once with saturated brine and dried with magnesium sulfate. The magnesium sulfate was removed by filtration and the filtrate was concentrated to obtain the solid product. The solid was washed with chloroform to give a final 15 g of white solid target product 4-trifluoromethylphenylboronic acid in 54% yield.

References

[1] Patent: WO2008/26614, 2008, A1. Location in patent: Page/Page column 93-95
[2] Journal of the Chemical Society - Perkin Transactions 1, 1999, # 17, p. 2513 - 2523
[3] Organic and Biomolecular Chemistry, 2012, vol. 10, # 33, p. 6693 - 6704
[4] Bioorganic and Medicinal Chemistry Letters, 2017, vol. 27, # 9, p. 1919 - 1922
[5] Journal of Organometallic Chemistry, 2017, vol. 846, p. 305 - 311

4-Trifluoromethylphenylboronic acid(128796-39-4)Related Product Information

• 4-Tolylboronic acid
• Benzotrifluoride
• 3,5-Dimethylphenylboronic acid
• 3-(Trifluoromethyl)benzoic acid
• 2-(Trifluoromethyl)benzoic acid
• Tolyltriazole
• (Trifluoromethyl)trimethylsilane
• 3'-(Trifluoromethyl)acetophenone
• Phenylboronic acid
• Phenylmethylsulfonyl fluoride
• 3-（trifluoromethyl) Cinnamaldehyde
• 3-(Trifluoromethyl)benzaldehyde
• 4-(Trifluoromethyl)benzaldehyde
• 1-Bromo-4-(trifluoromethoxy)benzene
• 4-Aminobenzotrifluoride
• 4-(Trifluoromethoxy)aniline
• 4-Trifluoromethylphenol
• 4-(Trifluoromethyl)benzoic acid