Ethyl oxazole-4-carboxylate Chemical Properties

Melting point:

48°C

Boiling point:

101°C 14mm

Density 

1.177 g/mL at 25 °C

refractive index 

n20/D 1.467

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

form 

powder to lump to clear liquid

pka

0.38±0.10(Predicted)

color 

White or Colorless to Almost white or Almost colorless

InChI

InChI=1S/C6H7NO3/c1-2-10-6(8)5-3-9-4-7-5/h3-4H,2H2,1H3

InChIKey

UBESIXFCSFYQNK-UHFFFAOYSA-N

SMILES

O1C=C(C(OCC)=O)N=C1

CAS DataBase Reference

23012-14-8(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Safety Statements 

24/25

WGK Germany 

3

Hazard Note 

Irritant

HS Code 

2934999090

Ethyl oxazole-4-carboxylate Usage And Synthesis

Uses

Used for the Palladium-Catalyzed Synthesis of (Hetero)aryloxazoles.^[1]

Synthesis

The general procedure for the synthesis of ethyl oxazole-4-carboxylate from ethyl isocyanoylacetate was as follows: formic acid (8.62 mL, 228 mmol) was added in batches to anhydrous THF (200 mL), and the phenomenon of gas escape was observed. The mixture was stirred for 30 min to form a sol. Subsequently, a solution of ethyl isocyanoacetate (25 mL, 228 mmol) and triethylamine (Et3N, 60.5 mL, 434 mmol) was added to the reaction mixture. The mixture was stirred at room temperature for 1 hour and then changed to reflux conditions overnight. After the reaction was completed, the mixture was cooled to room temperature. Water was added and the mixture was extracted with ether (Et2O, 3 times). The organic phases were combined, dried with magnesium sulfate (MgSO4), filtered and concentrated. The residue was purified by fast column chromatography (FC, eluent: ethyl acetate/heptane, ratio graded from 1:5 to 1:3 and finally to 1:1) to afford ethyl oxazole-4-carboxylate (27.2 g, 84% yield). LC-MS analysis resulted in a retention time (tR) = 0.58 min and a mass-to-charge ratio in the electrosprayed positive ion mode (ES+) (m/z) = 142.07 .

References

[1] CéCILE VERRIER. Palladium-Catalyzed Direct (Hetero)arylation of Ethyl Oxazole-4-carboxylate: An Efficient Access to (Hetero)aryloxazoles[J]. The Journal of Organic Chemistry, 2008, 73 18: 7383-7386. DOI:10.1021/jo801093n.

Ethyl oxazole-4-carboxylate(23012-14-8)Related Product Information

• Benzocaine
• Ethylparaben
• Ethanol
• Ethyl acetate
• Ethyl acrylate
• Ethyl formate
• ISOXADIFEN-ETHYL
• Oxazole
• Ethyl pyruvate
• Tris(trimethylsilyl)phosphate
• Urethane
• RESMETHRIN
• Ethyl cyanoformate
• Ethyl cyanoacetate
• ETHYL OXAZOLE-2-CARBOXYLATE
• Ethyl chloroformate
• Ethyl 5-methylisoxazole-4-carboxylate
• Ethyl 5-methyl-3-phenylisoxazole-4-carboxylate