ChemicalBook Product Catalog Pharmaceutical intermediates Heterocyclic compound Pyridine compound Aminopyridine 4-Amino-2-trifluoromethylpyridine

4-Amino-2-trifluoromethylpyridine

Product Name4-Amino-2-trifluoromethylpyridine
CAS147149-98-2
MFC6H5F3N2
MW162.11
EINECS
MOL File147149-98-2.mol

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
Storage Class	6.1C - Combustible acute toxic Cat.3 toxic compounds or compounds which causing chronic effects
Hazard Classifications	Acute Tox. 3 Oral Eye Irrit. 2

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

4-Nitro-2-trifluoromethylpyridine-N-oxide

147149-97-1

147149-98-2

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

4-Amino-2-trifluoromethylpyridine

Chemical Properties

Safety Information

Usage And Synthesis

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