6-(TRIFLUOROMETHYL)URACIL

Bezeichnung:6-(TRIFLUOROMETHYL)URACIL

CAS-Nr672-45-7

Englisch Name:6-(TRIFLUOROMETHYL)URACIL

CBNumberCB4457563

SummenformelC5H3F3N2O2

Molgewicht180.08

MOL-Datei672-45-7.mol

6-(TRIFLUOROMETHYL)URACIL physikalisch-chemischer Eigenschaften

Schmelzpunkt	230-235 °C (lit.)
Dichte	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)
Aggregatzustand	Powder
Aussehen	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 Datenbank	672-45-7(CAS DataBase Reference)
NIST chemische Informationen	Uracil, 6-(trifluoromethyl)-,(672-45-7)

Sicherheit

Kennzeichnung gefährlicher	Xi
S-Sätze:	24/25
WGK Germany	3
HazardClass	IRRITANT
HS Code	29335990
Speicherklasse	11 - Combustible Solids

Gefahreninformationscode (GHS)

6-(TRIFLUOROMETHYL)URACIL Chemische Eigenschaften,Einsatz,Produktion Methoden

Verwenden
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
Synthese

372-31-6

57-13-6

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).
Einzelnachweise
[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 Upstream-Materialien And Downstream Produkte

6-(TRIFLUOROMETHYL)URACIL Anbieter Lieferant Produzent Hersteller Vertrieb Händler.

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