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

CAS DataBase Reference

672-45-7(CAS DataBase Reference)

NIST Chemistry Reference

Uracil, 6-(trifluoromethyl)-,(672-45-7)

Safety Information

Hazard Codes 

Xi

Safety Statements 

24/25

WGK Germany 

3

HazardClass 

IRRITANT

HS Code 

29335990

MSDS

• Language:English Provider:SigmaAldrich
• Language:English Provider:ALFA

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(672-45-7)Related Product Information

• 2-Amino-4-hydroxy-6-(trifluoromethyl)uracil
• 6-(TRIFLUOROMETHYL)URACIL
• BUTAFENACIL
• 5-(TRIFLUOROMETHYL)URACIL,5-(Trifluoromethyl)uracil,97%,5-(Trifluoromethyl)uracil98%,5-(TRIFLUOROMETHYL)URACIL: 98.5%
• Trifluridine
• FLUACRYPYRIM
• 5,6-DIHYDRO-5-(TRIFLUOROMETHYL)URACIL
• 5-TRIFLUOROMETHYL URACIL, [2-13C-1,3-15N]-
• 4-METHOXY-2-(2,4,5-TRICHLOROPHENOXY)-6-(TRIFLUOROMETHYL)PYRIMIDINE
• 3-ethyl-6-(trifluoromethyl)-2,4(1H,3H)-pyrimidinedione
• 3-propyl-6-(trifluoromethyl)-2,4(1H,3H)-pyrimidinedione
• 3-(3-chlorophenyl)-6-(trifluoromethyl)-2,4(1H,3H)-pyrimidinedione
• 3-allyl-6-(trifluoromethyl)-2,4(1H,3H)-pyrimidinedione
• 3-cyclohexyl-6-(trifluoromethyl)-2,4(1H,3H)-pyrimidinedione
• 1,3-DIMETHYL-6-TRIFLUOROMETHYL-1H-PYRIMIDINE-2,4-DIONE
• 3-(2-chlorophenyl)-6-(trifluoromethyl)-2,4(1H,3H)-pyrimidinedione
• 4-METHOXY-2-(2-NAPHTHYLOXY)-6-(TRIFLUOROMETHYL)PYRIMIDINE
• 3-(4-CHLOROPHENYL)-6-(TRIFLUOROMETHYL)-2,4(1H,3H)-PYRIMIDINEDIONE