2-Hydroxy-5-trifluoromethylpyridine Chemical Properties

Melting point:

145-149 °C (lit.)

Boiling point:

221.2±40.0 °C(Predicted)

Density 

1.398±0.06 g/cm3(Predicted)

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

solubility 

DMSO (Soluble), Ethanol (Sparingly), Methanol (Sightly)

pka

9.55±0.10(Predicted)

form 

Crystalline Powder

color 

White to beige

InChI

InChI=1S/C6H4F3NO/c7-6(8,9)4-1-2-5(11)10-3-4/h1-3H,(H,10,11)

InChIKey

BYRJSCNPUHYZQE-UHFFFAOYSA-N

SMILES

C1(=O)NC=C(C(F)(F)F)C=C1

CAS DataBase Reference

33252-63-0(CAS DataBase Reference)

EPA Substance Registry System

2(1H)-Pyridinone, 5-(trifluoromethyl)- (33252-63-0)

Safety Information

Hazard Codes 

Xi,Xn

Risk Statements 

36/37/38-65-20/21/22-20/21

Safety Statements 

26-36

WGK Germany 

3

HazardClass 

IRRITANT

HS Code 

29339900

MSDS

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

2-Hydroxy-5-trifluoromethylpyridine Usage And Synthesis

Chemical Properties

Yellow to brown powder

Uses

2-Hydroxy-5-(trifluoromethyl)pyridine (cas# 33252-63-0) is a compound useful in organic synthesis.

General Description

2-Hydroxy-5-(trifluoromethyl)pyridine, a pyridine derivative, is a heterocyclic building block. They have useful applications in catalysis, drug design, molecular recognition, and natural product synthesis.

Synthesis

General procedure for the synthesis of 2-hydroxy-5-trifluoromethylpyridine from 6-hydroxynicotinic acid: 6-hydroxynicotinic acid (18.2 g, 0.13 mol), anhydrous hydrofluoric acid (2.6 mL, 0.13 mol, ≥95 wt%) and sulfur tetrafluoride (42.1 g, 0.39 mol) were added to a stainless steel pressure tank. The mixture was heated to 100 °C and reacted at 0.15 MPa pressure for 12 hours. The gaseous product generated during the reaction was treated by an exhaust gas absorption unit. Upon completion of the reaction, the remaining product was transferred to a polytetrafluoroethylene vessel and heated to 40°C to remove residual hydrogen fluoride. Subsequently, the product was dissolved in 150 mL of water and the pH was adjusted to 6.8-7.2 with saturated sodium carbonate solution. the aqueous phase was extracted with chloroform, and the organic phases were combined and dried. After filtration and drying, 2-hydroxy-5-trifluoromethylpyridine (15.3 g, 0.094 mol) was obtained in 72% yield.

References

[1] Patent: CN102875453, 2016, B. Location in patent: Paragraph 0023

2-Hydroxy-5-trifluoromethylpyridine(33252-63-0)Related Product Information

• 3-(Trifluoromethyl)benzaldehyde
• 2-Hydroxy-5-methylpyridine
• 3-Hydroxypyridine
• 4-Methylpyridine
• 2-Fluoro-5-trifluoromethylpyridine
• 2-(Trifluoromethyl)pyridine
• 2-Hydroxypyridine
• 2-(Trifluoromethyl)benzoic acid
• 3-Aminobenzotrifluoride
• 2-Chloro-5-trifluoromethylpyridine
• 4-(Trifluoromethyl)pyridine
• 3-Trifluoromethylpyridine
• Trifluoromethanesulfonic acid
• CHLOROPHOSPHONAZO III
• 2,6-Lutidine
• Azamethiphos
• 2,4,6-Collidine
• 2-Hydroxy-4-(trifluoromethyl)pyridine