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ChemicalBook--->CAS DataBase List--->672-45-7

672-45-7

672-45-7 Structure

672-45-7 Structure
IdentificationMore
[Name]

6-(TRIFLUOROMETHYL)URACIL
[CAS]

672-45-7
[Synonyms]

6-(TRIFLUOROMETHYL)-2,4-(1H,3H)PYRIMIDINEDIONE
6-(TRIFLUOROMETHYL)URACIL
6-(TRIFLUOROMETHYL)URACYL
2,4(1H,3H)-Pyrimidinedione, 6-(trifluoromethyl)-
6-(Trifluoromethyl)-2,4-pyrimidinediol
6-Trifluoromethyl-1H-pyrimidine-2,4-dione
6-(Trifluoromethyl)pyrimidine-2,4(1H,3H)-dione
2,4-Dihydroxy-6-trifluoromethylpyrimidine
[EINECS(EC#)]

211-593-2
[Molecular Formula]

C5H3F3N2O2
[MDL Number]

MFCD01011762
[Molecular Weight]

180.08
[MOL File]

672-45-7.mol
Chemical PropertiesBack Directory
[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
[form ]

Powder
[pka]

4.70±0.10(Predicted)
[Appearance]

White to off-white Solid
[CAS DataBase Reference]

672-45-7(CAS DataBase Reference)
[NIST Chemistry Reference]

Uracil, 6-(trifluoromethyl)-,(672-45-7)
Safety DataBack Directory
[Hazard Codes ]

Xi
[Safety Statements ]

24/25
[WGK Germany ]

3
[Hazard Note ]

Irritant
[HazardClass ]

IRRITANT
[HS Code ]

29335990
Hazard InformationBack Directory
[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-trifluoroacetoacetate

372-31-6

Urea

57-13-6

6-(TRIFLUOROMETHYL)URACIL

672-45-7

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
Spectrum DetailBack Directory
[Spectrum Detail]

6-(TRIFLUOROMETHYL)URACIL(672-45-7)1HNMR
6-(TRIFLUOROMETHYL)URACIL(672-45-7)IR
Well-known Reagent Company Product InformationBack Directory
[Alfa Aesar]

6-(Trifluoromethyl)uracil, 97%(672-45-7)
[Sigma Aldrich]

672-45-7(sigmaaldrich)
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