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| | N-[4-Cyano-3-(trifluoromethyl)phenyl]-2-methacrylamide Basic information |
| Product Name: | N-[4-Cyano-3-(trifluoromethyl)phenyl]-2-methacrylamide | | Synonyms: | N-(4-Cyano-3-(trifluoromethyl)phenyl)-2-methyl-2-Propenamide;N-Methacryloyl-4-cyano-3-trifluoromethylaniline;2-Methyl-N-[(4-cyano-3-trifluoromethyl)phenyl]-propenamide;N-[4-CYANO-3-(TRIFLUOROMETHYL)PHENYL]-2-METHACRYLAMIDE;N-{[4-cyano-3-(trifluoroMethyl)phenyl]Methyl}prop-2-enaMide;N-[4-Cyano-3-(trifluoromethyl)phenyl]-2-methylacrylamide;N-[4-Cyano-3-(trifluoromethyl)phenyl]methacrylamide;2-Propenamide, N-[4-cyano-3-(trifluoromethyl)phenyl]-2-methyl- | | CAS: | 90357-53-2 | | MF: | C12H9F3N2O | | MW: | 254.21 | | EINECS: | 427-880-2 | | Product Categories: | Chemical intermediate for Bicalutamide | | Mol File: | 90357-53-2.mol | ![N-[4-Cyano-3-(trifluoromethyl)phenyl]-2-methacrylamide Structure](CAS/GIF/90357-53-2.gif) |
| | N-[4-Cyano-3-(trifluoromethyl)phenyl]-2-methacrylamide Chemical Properties |
| Melting point | 137-139 °C | | Boiling point | 395.5±42.0 °C(Predicted) | | density | 1.28 | | storage temp. | 2-8°C | | solubility | Acetonitrile (Slightly), Chloroform (Slightly) | | pka | 12.19±0.70(Predicted) | | form | Solid | | 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 |
| RIDADR | 3077 | | HS Code | 2926.90.5050 | | HazardClass | 9 | | PackingGroup | III |
| | N-[4-Cyano-3-(trifluoromethyl)phenyl]-2-methacrylamide Usage And Synthesis |
| 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 |
| | N-[4-Cyano-3-(trifluoromethyl)phenyl]-2-methacrylamide Preparation Products And Raw materials |
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