Ethyl pyrazole-4-carboxylate Chemical Properties

Melting point:

78-80 °C (lit.)

Boiling point:

138-140 °C/3 mmHg (lit.)

Density 

1.2850 (rough estimate)

refractive index 

1.5010 (estimate)

Flash point:

138-140°C/3mm

storage temp. 

Sealed in dry,Room Temperature

solubility 

Miscible with acetone.

form 

Crystalline Powder

pka

11.70±0.50(Predicted)

color 

White to pale yellow

InChI

InChI=1S/C6H8N2O2/c1-2-10-6(9)5-3-7-8-4-5/h3-4H,2H2,1H3,(H,7,8)

InChIKey

KACZQOKEFKFNDB-UHFFFAOYSA-N

SMILES

N1C=C(C(OCC)=O)C=N1

LogP

0.909 (est)

CAS DataBase Reference

37622-90-5(CAS DataBase Reference)

NIST Chemistry Reference

4-(C2H5COO)-pyrazole(37622-90-5)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-37/39

WGK Germany 

3

HazardClass 

IRRITANT

HS Code 

29331990

MSDS

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

Ethyl pyrazole-4-carboxylate Usage And Synthesis

Chemical Properties

White to pale yellow crystalline powder

Uses

Used for the synthesis of isoxazole-4-carboxylic acid derivatives and isoxazole-3,5-dicarboxamides as herbicides.

Uses

Ethyl pyrazole-4-carboxylate is used for the synthesis of isoxazole-4-carboxylic acid derivatives and isoxazole-3,5-dicarboxamides.

Synthesis Reference(s)

Journal of Heterocyclic Chemistry, 30, p. 865, 1993 DOI: 10.1002/jhet.5570300404

Synthesis

The general procedure for the synthesis of ethyl 4-pyrazolecarboxylate from ethyl 2-formyl-3-oxopropanoate was as follows: 6.2 g (193 mmol) of hydrazine was slowly added to a solution of 27.6 g (192 mmol) of (ethoxycarbonyl)malondialdehyde dissolved in 150 mL of ethanol under ice bath cooling conditions. The reaction mixture was stirred at room temperature for 17 hours to complete the reaction. Subsequently, ethanol was removed from the reaction mixture by vacuum distillation. The residue was purified by silica gel column chromatography using a solvent mixture of dichloromethane and ethyl acetate as the unfolding agent, resulting in 19.4 g (72.4% yield) of ethyl 1H-pyrazole-4-carboxylate as yellow crystals.1H-NMR [CDCl3/TMS, δ (ppm)]: 8.08 (2H, s), 5.30 (1H, s), 4.31 ( 2H, q), 1.36 (3H, t).

References

[1] Tetrahedron, 2008, vol. 64, # 33, p. 7745 - 7758
[2] Journal of Heterocyclic Chemistry, 1993, vol. 30, # 4, p. 865 - 872
[3] Patent: EP1364946, 2003, A1. Location in patent: Page/Page column 196
[4] Patent: US2005/256004, 2005, A1. Location in patent: Page/Page column 32

Ethyl pyrazole-4-carboxylate(37622-90-5)Related Product Information

• Ethyl acrylate
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• Ethylparaben
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• Pyrazole
• Ethyl acetate
• Urethane
• Ethylbenzene
• RESMETHRIN
• CHLOROETHANE
• Ethyl chloroformate
• ETHYL 2-PHENYL-3-(TRIFLUOROMETHYL)PYRAZOLE-4-CARBOXYLATE
• ETHYL 5-AMINO-1-METHYLPYRAZOLE-4-CARBOXYLATE
• ETHYL 5-METHYL-1-PHENYL-1H-PYRAZOLE-4-CARBOXYLATE
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• ETHYL 3-(TRIFLUOROMETHYL)PYRAZOLE-4-CARBOXYLATE