| Identification | Back Directory | [Name]
5-AMINO-3-(TRIFLUOROMETHYL)PICOLINONITRILE | [CAS]
573762-62-6 | [Synonyms]
5-AMINO-3-(TRIFLUOROMETHYL)PICOLINONITRILE
5-AMino-3-(trifluroMethyl) picolinonitrile
5-Amino-3-(trifluoromethyl)2-cyanopyridine
5-Amino-2-cyano-3-(trifluoromethyl)pyridine
5-Amino-3-(trifluoromethyl)picolinonitrile 97%
5-AMino-3-(trifluoroMethyl)pyridine-2-carbonitrile
5-Amino-3-(trifluoromethyl)-2-pyridinecarbonitrile
2-Pyridinecarbonitrile, 5-amino-3-(trifluoromethyl)-
5-amino-3-((trifluoromethyl))-pyridin-2-carbonitrile
5-Amino-3-(trifluoromethyl)pyridine-2-carbonitrile(For export only) | [EINECS(EC#)]
815-137-9 | [Molecular Formula]
C7H4F3N3 | [MDL Number]
MFCD17010171 | [MOL File]
573762-62-6.mol | [Molecular Weight]
187.122 |
| Chemical Properties | Back Directory | [Boiling point ]
362.2±42.0 °C(Predicted) | [density ]
1.45±0.1 g/cm3(Predicted) | [storage temp. ]
Keep in dark place,Inert atmosphere,Room temperature | [pka]
-1.52±0.10(Predicted) | [Appearance]
Off-white to yellow Solid | [InChI]
InChI=1S/C7H4F3N3/c8-7(9,10)5-1-4(12)3-13-6(5)2-11/h1,3H,12H2 | [InChIKey]
WLMSCOVORZUSNW-UHFFFAOYSA-N | [SMILES]
C1(C#N)=NC=C(N)C=C1C(F)(F)F |
| Hazard Information | Back Directory | [Description]
5-Amino-3-(trifluoromethyl)picolinonitrile is one of the key intermediates of apalutamide (N-2). As a second-generation nonsteroidal androgen receptor inhibitor, apalutamide can prevent the binding of androgens to their receptors and block the translocation of androgen receptor (AR) into the nuclei of cancer cells; in addition, it can regulate androgen activity and inhibit the growth of cancer cells. | [Uses]
5-AMINO-3-(TRIFLUOROMETHYL)PICOLINONITRILE is a pyridine heterocyclic organic compound, which can be used as pharmaceutical intermediates. | [Synthesis]
General procedure for the synthesis of 5-amino-3-(trifluoromethyl)cyanopyridine from 2-cyano-5-nitro-3-(trifluoromethyl)pyridine: 2-cyano-3-(trifluoromethyl)-5-nitropyridine A10 (0.095 g, 0.44 mmol) was reacted with powdered iron (0.112 g, 2 mmol) in a mixed solvent of ethyl acetate (1 ml) and acetic acid (1 ml) The reaction was heated for 15 hours in a mixture of ethyl acetate (1ml) and acetic acid (1ml). After completion of the reaction, the solid particles were removed by diatomaceous earth filtration and the filtrate was concentrated. Finally, the target compound A11 (0.075 g, 0.4 mmol, 91% yield) was purified by column chromatography (eluent: EtOAc:pentane=1:1). | [References]
[1] Patent: JP2016/11315, 2016, A. Location in patent: Paragraph 0040; 0047
[2] Patent: US9388159, 2016, B2. Location in patent: Page/Page column 11; 12; 19
[3] Patent: WO2008/119015, 2008, A2. Location in patent: Page/Page column 47-48
[4] Patent: US2016/152592, 2016, A1. Location in patent: Paragraph 0073; 0080; 0081
[5] Bioorganic and Medicinal Chemistry Letters, 2017, vol. 27, # 12, p. 2803 - 2806 |
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