3-CYANO-2,6-DIHYDROXY-4-(TRIFLUOROMETHYL)PYRIDINE Chemical Properties

Melting point:

285°C

Boiling point:

267.8±40.0 °C(Predicted)

Density 

1.63±0.1 g/cm3(Predicted)

storage temp. 

Inert atmosphere,Room Temperature

pka

2.57±0.58(Predicted)

Appearance

Off-white to light brown Solid

Safety Information

Hazard Codes 

Xi,T

Risk Statements 

25-36

Safety Statements 

26-45

HazardClass 

IRRITANT

HS Code 

2933399990

3-CYANO-2,6-DIHYDROXY-4-(TRIFLUOROMETHYL)PYRIDINE Usage And Synthesis

Chemical Properties

Pale yellow solid

Uses

3-Cyano-2,6-dihydroxy-4-(trifluoromethyl)pyridine is used as a reagent in the synthesis of novel monoindolyl-4-trifluoromethylpyridines and bisindolyl-4-trifluoromethylpyridines which can be used as potential antitumor agents.

Synthesis

General procedure for the synthesis of 2,6-dihydroxy-3-cyano-4-(trifluoromethyl)pyridine from ethyl trifluoroacetoacetate and cyanoacetamide: 29.8 g (0.53 mol) of potassium hydroxide was slowly added to a 250 mL four-necked flask fitted with a mechanical stirrer and a reflux condenser, followed by the addition of 100 mL of methanol, and stirred until dissolved and set aside. In another 500 mL four-necked flask equipped with a mechanical stirrer, a constant pressure dropping funnel, a drying tube and a reflux condenser, 43.4 g (0.52 mol) of cyanoacetamide and 150 mL of methanol were added and heated to reflux with mechanical stirring. After the reaction solution changed from turbid to light yellow and transparent, 100 g (0.54 mol) of ethyl trifluoroacetoacetate was added. Maintaining reflux, a preconfigured methanol solution of potassium hydroxide was added slowly and dropwise. The reaction was heated and refluxed for 24 h. The complete reaction of cyanoacetamide was confirmed by TLC monitoring. The reflux unit was changed to a distillation unit and about 3/4 of the methanol was recovered. Cold water was added to the residue and after cooling to room temperature, the pH was adjusted to 3-4 with dilute hydrochloric acid and stirring was continued for 0.5 hours. The reaction mixture was filtered and the filter cake was washed with water to give the white solid product 2,6-dihydroxy-3-cyano-4-(trifluoromethyl)pyridine. The product was dried at 80 °C to constant weight to give 84.5 g final in 80.1% yield and 98% HPLC purity.

References

[1] Patent: CN107382848, 2017, A. Location in patent: Paragraph 0034-0045

3-CYANO-2,6-DIHYDROXY-4-(TRIFLUOROMETHYL)PYRIDINE(3335-46-4)Related Product Information

• 4-(Trifluoromethyl)pyridine
• 3-Cyano-2,6-dihydroxy-4-methylpyridine
• 6-hydroxy-4-methyl-2-pyridone
• 3-CYANO-2,6-DIHYDROXY-4-(TRIFLUOROMETHYL)PYRIDINE
• 3-CYANO-2,6-DIHYDROXY-4-(TRIFLUOROMETHYL)PYRIDINE DIHYDRATE
• 2,6-Dihydroxy-3,4-dimethylpyridine
• 4-(TRIFLUOROMETHYL)PYRIDINE-2,6-DIOL