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| | 6-(Trifluoromethyl)uracil Basic information |
| Product Name: | 6-(Trifluoromethyl)uracil | | Synonyms: | 6-(TRIFLUOROMETHYL)URACYL;6-(TRIFLUOROMETHYL)-2,4-(1H,3H)PYRIMIDINEDIONE;2,4(1H,3H)-Pyrimidinedione, 6-(trifluoromethyl)-;6-(Trifluoromethyl)-2,4-pyrimidinediol;6-Trifluoromethyl-1H-pyrimidine-2,4-dione;2,4-Dihydroxy-6-trifluoromethylpyrimidine;6-(trifluoromethyl)pyrimidine-2,4-diol,6-(Trifluoromethyl)uracil;6-(Trifluoromethyl)uracil 98% | | CAS: | 672-45-7 | | MF: | C5H3F3N2O2 | | MW: | 180.08 | | EINECS: | 211-593-2 | | Product Categories: | Pyrimidine series;Heterocyclic Compounds;Building Blocks;Heterocyclic Building Blocks;Pyrimidines | | Mol File: | 672-45-7.mol |  |
| | 6-(Trifluoromethyl)uracil Chemical Properties |
| Melting point | 230-235 °C (lit.) | | density | 1.554±0.06 g/cm3(Predicted) | | storage temp. | under inert gas (nitrogen or Argon) at 2-8°C | | pka | 4.70±0.10(Predicted) | | form | Powder | | Appearance | White to off-white Solid | | InChI | 1S/C5H3F3N2O2/c6-5(7,8)2-1-3(11)10-4(12)9-2/h1H,(H2,9,10,11,12) | | InChIKey | IROWWTVZNHKLLE-UHFFFAOYSA-N | | SMILES | FC(F)(F)C1=CC(=O)NC(=O)N1 | | CAS DataBase Reference | 672-45-7(CAS DataBase Reference) | | NIST Chemistry Reference | Uracil, 6-(trifluoromethyl)-,(672-45-7) |
| Hazard Codes | Xi | | Safety Statements | 24/25 | | WGK Germany | 3 | | HazardClass | IRRITANT | | HS Code | 29335990 | | Storage Class | 11 - Combustible Solids |
| | 6-(Trifluoromethyl)uracil Usage And Synthesis |
| Uses | 6-(Trifluoromethyl)-2,4(1H,3H)-pyrimidinedione is an anticancer drug, produced from catalytic trifluoromethylation of uracil. | | Synthesis Reference(s) | The Journal of Organic Chemistry, 24, p. 113, 1959 DOI: 10.1021/jo01083a607 | | Synthesis | Ethyl 4,4,4-trifluoro-3-oxobutanoate (3 g, 16.30 mmol) was dissolved in ethanol (30 mL) under argon protection and urea (978 mg, 16.30 mmol) was added with stirring. Subsequently, freshly prepared sodium ethoxide solution (made by reacting 750 mg of sodium metal with 30 mL of anhydrous ethanol) was added to the reaction system. The reaction mixture was heated to 90 °C and the reaction was stirred at this temperature for 24 hours. The reaction process was monitored by thin layer chromatography (TLC). Upon completion of the reaction, volatile solvents were removed by distillation under reduced pressure, and the residue was diluted with water (25 mL), acidified with 1N hydrochloric acid (10 mL) to pH < 7, and then extracted with ethyl acetate (2 x 40 mL). The organic phases were combined, dried with anhydrous sodium sulfate, filtered and concentrated under reduced pressure to give the target product 6-(trifluoromethyl)uracil (650 mg, 22% yield) as a white solid. Thin layer chromatographic conditions: 5% methanol/dichloromethane (Rf=0.3).1H-NMR (DMSO-d6, 500MHz) data: δ 11.07 (s, 1H), 11.54 (s, 1H), 6.07 (s, 1H). | | References | [1] Patent: WO2015/57945, 2015, A1. Location in patent: Paragraph 00121
[2] Journal of Organic Chemistry, 1959, vol. 24, p. 113
[3] Journal of the American Chemical Society, 1958, vol. 80, p. 5744,5751 |
| | 6-(Trifluoromethyl)uracil Preparation Products And Raw materials |
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