2-(Trifluormethoxy)phenylboronic acid Chemical Properties

Melting point:

118-120°C

Boiling point:

267.2±50.0 °C(Predicted)

Density 

1.41±0.1 g/cm3(Predicted)

Flash point:

110℃

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

solubility 

soluble in Methanol

form 

Powder or Crystalline Powder

pka

8.14±0.53(Predicted)

color 

White to pale brown

BRN 

8766167

InChIKey

AIJCNTOYZPKURP-UHFFFAOYSA-N

CAS DataBase Reference

175676-65-0(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi,Xn

Risk Statements 

36/37/38-20/21/22-22

Safety Statements 

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

WGK Germany 

3

Hazard Note 

Irritant

HazardClass 

MOISTURE SENSITIVE, KEEP COLD

HS Code 

29163990

MSDS

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2-(Trifluormethoxy)phenylboronic acid Usage And Synthesis

Chemical Properties

White to light brown solid

Uses

2-(Trifluoromethoxy)phenylboronic Acid is a reagent that is used for the preparation of ERβ receptor that is selective towards 4-hydroxybiphenyls.

Uses

suzuki reaction

General Description

May contain varying amounts of anhydride.

Synthesis

The general procedure for the synthesis of 2-(trifluoromethoxy)phenylboronic acid from 1-bromo-2-(trifluoromethoxy)benzene was as follows: n-butyllithium (5.9 mL, 9.5 mmol) was slowly added dropwise to a solution of 1-bromo-2-(trifluoromethoxy)benzene (2 g, 8.2 mmol) in tetrahydrofuran (28 mL) at -78 °C and the reaction was stirred for 45 min. Subsequently, triisopropyl borate (2.58 mL, 11.1 mmol) was slowly added dropwise to the reaction mixture and the reaction system was slowly warmed to room temperature over 16 hours. Upon completion of the reaction, the reaction was quenched with water, the pH was adjusted to alkaline with 2 N NaOH solution and subsequently extracted with ethyl acetate. The aqueous phase was acidified to pH acidic with 2 N HCl solution, stirred for 1 h at room temperature and again extracted with ethyl acetate. The organic phases were combined, washed sequentially with water and saturated saline and dried over anhydrous sodium sulfate. After filtration, the organic phase was concentrated under reduced pressure to afford the target product 2-(trifluoromethoxy)phenylboronic acid (1.10 g, 65% yield) as a white solid. The product was confirmed by NMR hydrogen spectroscopy (CDCl3): δ 7.96 (dd, J = 7.2, 1.6 Hz, 1H), 7.53 (ddd, J = 9.1, 7.3, 1.8 Hz, 1H), 7.38 (td, J = 7.3, 0.7 Hz, 1H), 7.28 (d, J = 8.2 Hz, 1H), 5.25 (br s, 2H). Mass spectrometry analysis showed the molecular ion peak m/e 206.9 (M + 1)+.

References

[1] Patent: WO2004/92140, 2004, A1. Location in patent: Page 38
[2] Patent: WO2005/97136, 2005, A1. Location in patent: Page/Page column 30

2-(Trifluormethoxy)phenylboronic acid(175676-65-0)Related Product Information

• p-Anisaldehyde
• 4-Trifluoromethylphenylboronic acid
• 4-(Trifluoromethoxy)benzaldehyde
• 4-Methoxybenzyl alcohol
• 4-Methoxybenzyl cyanide
• 4'-(Trifluoromethoxy)acetophenone
• 4-Methoxybenzoyl chloride
• 4-(Trifluoromethoxy)chlorobenzene
• (Trifluoromethoxy)benzene
• Phenylboronic acid
• 2,3,4-Trimethoxybenzaldehyde
• 2-(Trifluoromethoxy)aniline
• Anisole
• Ethyl 2-(Chlorosulfonyl)acetate
• Folic acid
• p-Trifluoromethoxy phenol
• (4-METHOXYPHENYL)-BORANE
• 4-(Trifluoromethoxy)aniline