| Identification | Back Directory | [Name]
4-Amino-2-trifluoromethylpyridine | [CAS]
147149-98-2 | [Synonyms]
Enasidenib Intermediate 4
2-trifluoromethyl-4-aminopyridine
2-(trifluoromethyl)pyridin-4-amin
2-(Trifluoromethyl)-4-pyridinamine
2-Ctrifluoromethyl/pyridin-4-amine
2-(Trifluoromethyl)pyridin-4-amine
2-Trifluoromethyl-pyridin-4-ylamine
4-Amino-2-(trifluoromethyl)-pyridine
4-Pyridinamine, 2-(trifluoromethyl)-
2-CTRIFLUOROMETHYL/PYRIDIN-4-AMINE,98%
4-Amino-2-(trifluoromethyl)pyridine HCl
CAS:147149-98-2 4-Amino-2-trifluoromethylpyridine
4-Amino-2-trifluoromethylpyridine ISO 9001：2015 REACH
2-(Trifluoromethyl)pyridin-4-amine (4-Amino-2-trifluoromethylpyridine) | [Molecular Formula]
C6H5F3N2 | [MDL Number]
MFCD09056877 | [MOL File]
147149-98-2.mol | [Molecular Weight]
162.12 |
| Chemical Properties | Back Directory | [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 |
| Hazard Information | Back Directory | [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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