6-(Trifluoromethyl)nicotinic acid Chemical Properties

Melting point:

193-197 °C(lit.)

Boiling point:

259.3±40.0 °C(Predicted)

Density 

1.484±0.06 g/cm3(Predicted)

storage temp. 

Inert atmosphere,Room Temperature

solubility 

Acetonitrile (Slightly), Methanol (Slightly)

form 

Solid

pka

2.96±0.10(Predicted)

color 

Pale Beige to Light Brown

InChI

InChI=1S/C7H4F3NO2/c8-7(9,10)5-2-1-4(3-11-5)6(12)13/h1-3H,(H,12,13)

InChIKey

JNYLMODTPLSLIF-UHFFFAOYSA-N

SMILES

C1=NC(C(F)(F)F)=CC=C1C(O)=O

CAS DataBase Reference

231291-22-8(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36

WGK Germany 

3

HazardClass 

IRRITANT

HS Code 

29333990

MSDS

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

6-(Trifluoromethyl)nicotinic acid Usage And Synthesis

Physical properties

6-Trifluoromethylnicotinic acid is a white powder with a melting point of 193-197 °C. It has a boiling point of 259.3℃ at 760 mmHg. Its density is 1.484 g/cm3. Its flash point, refractive index and vapor pressure are 110.6℃, 1.475 and 0.007mmHg at 25°C, respectively.

Uses

6-Trifluoromethyl Nicotinic Acid can be prepared to use Raf inhibitors to treat cancer.

Synthesis

To a 10L three-necked flask were added 1420 g of water, 2440 g of sulfuric acid, and 150 mL of glacial acetic acid, and 870 g (5 mol) of 6-(trifluoromethyl)nicotinonitrile was added slowly. The mixture was heated to reflux and kept overnight. Upon completion of the reaction, the reaction mixture was cooled, ice was added and the mixture was cooled using ice brine to precipitate a white solid. After filtration, the filtrate was extracted with ethyl acetate. The organic phases were combined and washed twice with water, followed by drying the organic phase to acidity. After washing, 930 g of 6-(trifluoromethyl)-3-pyridinecarboxylic acid was obtained as a beige solid in 97.3% yield.

References

[1] Patent: CN107298677, 2017, A. Location in patent: Paragraph 0036-0038
[2] Patent: CN107337638, 2017, A. Location in patent: Paragraph 0031; 0032; 0033
[3] Patent: EP1122242, 2001, A1
[4] Patent: US6673799, 2004, B1. Location in patent: Page column 16

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