5-Ethyluracil Chemical Properties

Melting point:

>300 °C(lit.)

Density 

1.164±0.06 g/cm3(Predicted)

storage temp. 

Sealed in dry,Room Temperature

form 

powder to crystal

pka

9.21±0.10(Predicted)

color 

White to Light yellow

λmax

265nm(EtOH)(lit.)

BRN 

119494

InChI

InChI=1S/C6H8N2O2/c1-2-4-3-7-6(10)8-5(4)9/h3H,2H2,1H3,(H2,7,8,9,10)

InChIKey

RHIULBJJKFDJPR-UHFFFAOYSA-N

SMILES

C1(=O)NC=C(CC)C(=O)N1

CAS DataBase Reference

4212-49-1(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36

WGK Germany 

3

HS Code 

29335990

MSDS

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

5-Ethyluracil Usage And Synthesis

Application

5-Ethyluracil is a pharmaceutical intermediate and an organic synthesis intermediate that can be used in laboratory research and development processes as well as in chemical and pharmaceutical synthesis.

Chemical Properties

Solid

Synthesis

Urea (19.39 g, 0.32 mol, JT Baker) was slowly added to fuming sulfuric acid (26-29.5% free SO3, 135 mL, 2.65 mol, Aldrich) under cooling in an ice-water bath over a period of 20 min, and the reaction temperature was controlled to be maintained at 8 to 15°C. After stirring for 30 min, ethyl 2-formylbutyrate was added dropwise over 18 min ( 46.55 g, 0.32 mol, from Example LC), keeping the reaction temperature constant. After continued stirring for 30 minutes, a second portion of urea (15.07 g, 0.25 mol) was added over 10 minutes at the same temperature. Subsequently, the reaction mixture was stirred at room temperature for 65 hours and then heated at 90-100°C for 2 hours (gas was observed to escape, the reaction was exothermic, and the temperature rose to 110°C). Upon completion of the reaction, the mixture was cooled to 30 °C using an ice water bath and ice (270 g) was slowly added to ensure that the temperature did not exceed 35 °C. The mixture was further cooled to 5 °C and stirred for 20 min. The precipitated solid was collected by filtration, washed sequentially with cold water, hexane and ether and dried by filtration to give 5-ethyluracil in 38.85 g (85.9%) yield.

References

[1] Patent: WO2004/41821, 2004, A1. Location in patent: Page 26

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