4-Amino-2-trifluoromethylpyridine Chemical Properties

Melting point:

58-62°C

Boiling point:

230.7±40.0 °C(Predicted)

Density 

1.368±0.06 g/cm3(Predicted)

storage temp. 

Keep in dark place,Inert atmosphere,Room temperature

form 

powder to crystal

pka

4.62±0.50(Predicted)

color 

White to Almost white

InChI

InChI=1S/C6H5F3N2/c7-6(8,9)5-3-4(10)1-2-11-5/h1-3H,(H2,10,11)

InChIKey

LYNBZRJTRHTSKI-UHFFFAOYSA-N

SMILES

C1(C(F)(F)F)=NC=CC(N)=C1

Safety Information

Hazard Codes 

T,Xi

Risk Statements 

25-36-43

Safety Statements 

26-36/37

RIDADR 

2811

WGK Germany 

3

HazardClass 

6.1

PackingGroup 

Ⅲ

HS Code 

29333990

4-Amino-2-trifluoromethylpyridine Usage And Synthesis

Chemical Properties

4-Amino-2-trifluoromethylpyridine can undergo a Chichibabin reaction to introduce an additional amine group in the para-position. It is employed in the synthesis of oral checkpoint kinase inhibitor for immunotherapy.

Uses

4-Amino-2-(trifluoromethyl)pyridine are involved in many syntheses of active pharmaceutical ingredients (APIs), such as naporafenib, a RAF inhibitor used in the treatment of RAF-driven cancers.

Synthesis

The general procedure for the synthesis of 2-trifluoromethyl-4-aminopyridine from the compound (CAS:147149-97-1) is as follows: 3) 0.86 g of the compound of Example 65.4 was dissolved in 50 mL of anhydrous ethanol at room temperature, and 88 mg of 10% palladium/carbon catalyst was added under argon protection. Subsequently, the reaction was hydrogenated for 3 hours at room temperature and 5 bar hydrogen pressure. Upon completion of the reaction, the reaction mixture was filtered through a depth filter and washed with ethanol. The filtrate was concentrated under reduced pressure and the residue was purified by silica gel column chromatography with the eluent being a 95:5 solvent mixture of dichloromethane/methanol. Compound 65.5 was finally obtained in 88% yield.1H NMR (δ, ppm): 8.10 (d, 1H), 6.9 (s, 1H), 6.65 (d, 1H), 6.52 (s, 2H).

References

[1] Bioorganic and Medicinal Chemistry, 2010, vol. 18, # 20, p. 7150 - 7163
[2] Patent: US2009/215728, 2009, A1. Location in patent: Page/Page column 56
[3] Patent: WO2010/126851, 2010, A1. Location in patent: Page/Page column 114
[4] Patent: WO2007/119055, 2007, A1. Location in patent: Page/Page column 34-35

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