4-Trifluoromethoxyphenylboronic acid Chemical Properties

Melting point:

123-127 °C(lit.)

Boiling point:

256.6±50.0 °C(Predicted)

Density 

1.41±0.1 g/cm3(Predicted)

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

solubility 

soluble in Methanol

pka

8.29±0.10(Predicted)

form 

Crystalline Powder

color 

White to beige

BRN 

8548201

InChI

InChI=1S/C7H6BF3O3/c9-7(10,11)14-6-3-1-5(2-4-6)8(12)13/h1-4,12-13H

InChIKey

HUOFUOCSQCYFPW-UHFFFAOYSA-N

SMILES

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

CAS DataBase Reference

139301-27-2(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi,Xn

Risk Statements 

36/37/38-20/21/22

Safety Statements 

37/39-26-36

WGK Germany 

3

Hazard Note 

Irritant

HS Code 

29319090

MSDS

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

4-Trifluoromethoxyphenylboronic acid Usage And Synthesis

Chemical Properties

white to beige crystalline powder

Uses

B-[4-(Trifluoromethoxy)phenyl]boronic Acid is a reagent used in the synthesis of orally bioavailable matrix metalloprotinase inhibitors. Also used in the preparation of chromen-4-one inhibitors used against DNA dependant protein kinases.

Application

4-Trifluoromethoxyphenylboronic acid can reactant involved in the synthesis of biologically active molecules including:
Lactate dehydrogenase inhibitors for use against cancer cell proliferation
Nitro-phenoxybenzoic acid derivatives for PAI-1 inhibition
PA-824 analogs for use as antituberculosis drugs
Modulators of survival motor neuron protein
Reactant involved in addition reactions and cross-coupling reactions including Suzuki-Miyaura cross-coupling

Synthesis

Example 1E Synthesis of 4-(trifluoromethoxy)phenylboronic acid: 1-bromo-4-(trifluoromethoxy)benzene (1.69 kg) and triisopropyl borate (1.46 kg) were dissolved in THF (6.75 L) at -70 °C. A hexane solution (3.27 L) of 2.25 M butyllithium was slowly added to this solution over a period of 2.3 hours, followed by stirring for 10 minutes. Next, the reaction was quenched with 6 M HCl (1.52 L) and stirred at room temperature for 18 hours. The reaction mixture was poured into a mixture of heptane (8.43 L) and 20% (w/w) aqueous sodium chloride solution (8.44 kg) and stirred for 10 min to separate the aqueous and organic phases. The organic phase was concentrated to give a white paste. The paste was dried in vacuum (100 mmHg) at ambient temperature while nitrogen was passed for 2 days. Subsequently, it was further dried at 40-50 °C for 18 h to give 1.306 kg (90.4% yield) of the target product 4-(trifluoromethoxy)phenylboronic acid as a solid. The product was characterized by 1H NMR (CDCl3, 300 MHz): δ 7.24-7.19 (m, 2H), 8.14-8.10 (m, 2H) and additional absorption peaks were observed at δ 7.19-7.15 (m, 2H) and 8.04-8.00 (m, 2H), which corresponded to the cyclic boronic acid trimer.

References

[1] Patent: US2002/19539, 2002, A1
[2] Patent: US2002/19539, 2002, A1

4-Trifluoromethoxyphenylboronic acid(139301-27-2)Related Product Information

• Anisole
• 4-(Trifluoromethoxy)chlorobenzene
• p-Trifluoromethoxy phenol
• 4'-(Trifluoromethoxy)acetophenone
• (4-METHOXYPHENYL)-BORANE
• 2-(Trifluoromethoxy)aniline
• (Trifluoromethoxy)benzene
• p-Anisaldehyde
• 4-Trifluoromethylphenylboronic acid
• 4-Methoxybenzoyl chloride
• 4-(Trifluoromethoxy)aniline
• 4-Methoxybenzoic acid
• 4-Methoxybenzyl cyanide
• 4'-Methoxyacetophenone
• 4-(Trifluoromethoxy)benzaldehyde
• 4-Methoxybenzyl alcohol
• 2-METHOXY-4-(TRIFLUOROMETHOXY)-PHENYLBORONIC ACID
• 2-Chloro-5-(trifluoromethyl)phenylboronic acid