| Identification | Back Directory | [Name]
N-[4-Cyano-3-(trifluoromethyl)phenyl]-2-methacrylamide | [CAS]
90357-53-2 | [Synonyms]
Bicalutamide Impurity 19
Bicalutamide Impurity 21
N-Methacryloyl-4-cyano-3-trifluoromethylaniline
N-[4-CYANO-3-(TRIFLUOROMETHYL)PHENYL]-2-METHACRYLAMIDE
N-[4-Cyano-3-(trifluoromethyl)phenyl]-2-methylacrylamide
N-[4-Cyano-3-(trifluoromethyl)phenyl]methacrylamide
2-Methyl-N-[(4-cyano-3-trifluoromethyl)phenyl]-propenamide
N-{[4-cyano-3-(trifluoroMethyl)phenyl]Methyl}prop-2-enaMide
N-(4-Cyano-3-(trifluoromethyl)phenyl)-2-methyl-2-Propenamide
2-Propenamide, N-[4-cyano-3-(trifluoromethyl)phenyl]-2-methyl- | [EINECS(EC#)]
1312995-182-4 | [Molecular Formula]
C12H9F3N2O | [MDL Number]
MFCD03411609 | [MOL File]
90357-53-2.mol | [Molecular Weight]
254.21 |
| Chemical Properties | Back Directory | [Melting point ]
137-139 °C | [Boiling point ]
395.5±42.0 °C(Predicted) | [density ]
1.28 | [storage temp. ]
Sealed in dry,2-8°C | [solubility ]
Acetonitrile (Slightly), Chloroform (Slightly) | [form ]
Solid | [pka]
12.19±0.70(Predicted) | [color ]
White to Off-White | [Stability:]
Light Sensitive | [InChI]
InChI=1S/C12H9F3N2O/c1-7(2)11(18)17-9-4-3-8(6-16)10(5-9)12(13,14)15/h3-5H,1H2,2H3,(H,17,18) | [InChIKey]
HHWDZLSGDDXUSM-UHFFFAOYSA-N | [SMILES]
C(NC1=CC=C(C#N)C(C(F)(F)F)=C1)(=O)C(C)=C |
| Hazard Information | Back Directory | [Uses]
N-[4-Cyano-3-(trifluoromethyl)phenyl]-2-methylacrylamide was used to prepare and observe selective androgen receptor modulator activity. | [Synthesis]
Methacryloyl chloride (2.63 mL, 27.16 mmol) was slowly added dropwise to a stirred N,N-dimethylacetamide (14 mL) solution of 4-amino-2-trifluoromethylbenzonitrile (3.4 mmol) under nitrogen protection for a controlled time period of 10 min and the reaction was carried out at room temperature. The progress of the reaction was monitored by TLC for 3 h or overnight (o.n.). Upon completion of the reaction, the reaction mixture was diluted with ethyl acetate (100 mL) and washed sequentially with saturated aqueous sodium bicarbonate solution (3 x 25 mL) and cold brine (4 x 50 mL). The organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure to remove the solvent. The crude product was purified by fast column chromatography to afford N-(4-cyano-3-trifluoromethylphenyl)methacrylamide in white solid form in 95% yield. The structure of the product was confirmed by 1H-NMR (CDCl3): δ 8.06 (d, J = 2.0 Hz, 1H), 7.99 (dd, J = 8.5 Hz, 2.0 Hz, 1H), 7.87 (bs, 1H), 7.82 (d, J = 8.5 Hz, 1H), 5.90-5.88 (m, 1H), 5.63-5.61 (m, 1H). 2.11-2.10 (m, 3H). | [References]
[1] European Journal of Medicinal Chemistry, 2016, vol. 118, p. 230 - 243
[2] Journal of Medicinal Chemistry, 2007, vol. 50, # 5, p. 1028 - 1040
[3] Bioorganic and Medicinal Chemistry, 2012, vol. 20, # 13, p. 4020 - 4031
[4] Journal of Medicinal Chemistry, 1988, vol. 31, # 5, p. 954 - 959
[5] Journal of Medicinal Chemistry, 2007, vol. 50, # 16, p. 3857 - 3869 |
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