2-HYDROXY-5-(TRIFLUOROMETHOXY)BENZALDEHYDE Chemical Properties

Melting point:

31-33 °C (lit.)

Boiling point:

82 °C/60 mmHg (lit.)

Density 

1.4251 (estimate)

Flash point:

>230 °F

storage temp. 

under inert gas (nitrogen or Argon) at 2-8°C

pka

7.56±0.18(Predicted)

form 

Low Melting Solid

color 

White to pale yellow

Sensitive 

Air Sensitive

BRN 

7023825

CAS DataBase Reference

93249-62-8(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-37/39

WGK Germany 

3

HazardClass 

IRRITANT

HS Code 

29130000

MSDS

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

2-HYDROXY-5-(TRIFLUOROMETHOXY)BENZALDEHYDE Usage And Synthesis

Chemical Properties

White to pale yellow low melting solid

Uses

2-Hydroxy-5-(trifluoromethoxy)benzaldehyde may be used in the preparation of :

• 2-[(E)-2-hydroxy-5-(trifluoromethoxy)benzylideneamino]-4-methylphenol
• (E)-2-((3-fluorophenylimino)methyl)-4-(trifluoromethoxy) phenol
• 2-[(E)-(naphthalen-2-ylimino) methyl]-4-(trifluoromethoxy) phenol

General Description

2-Hydroxy-5-(trifluoromethoxy)benzaldehyde is formed as intermediate during the biotransformation pathways of CP-122,721 in humans.

Synthesis

Step A: Boron tribromide (BBr3, 85.2 g, 341 mmol) was slowly added dropwise to a solution of 2-methoxy-5-(trifluoromethoxy)benzaldehyde (50.0 g, 227 mmol) in dichloromethane (DCM, 500 mL) at -20°C and under nitrogen protection. The reaction mixture was stirred at 0°C for 2 hours. Upon completion of the reaction, the reaction was quenched by the addition of ice chips, followed by pouring the mixture into an aqueous solution of saturated sodium bicarbonate (NaHCO3, 300 mL) and extracting with dichloromethane (DCM, 3 x 400 mL). The organic layers were combined, dried over anhydrous sodium sulfate and concentrated to give the crude product. The crude product was purified by silica gel column chromatography (eluent: hexane/ethyl acetate=20:1) to afford 2-hydroxy-5-(trifluoromethoxy)benzaldehyde (38.0 g, 81.0% yield). NMR hydrogen spectrum (400 MHz, CDCl3) δ 10.97 (s, 1H), 9.87 (s, 1H), 7.43-7.38 (m, 2H), 7.02 (d, J=8.0 Hz, 1H).

References

[1] Patent: WO2013/148851, 2013, A1. Location in patent: Paragraph 00244
[2] Patent: US2014/275172, 2014, A1. Location in patent: Paragraph 0842

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