Ethyl pyrazole-4-carboxylate

Product NameEthyl pyrazole-4-carboxylate
CAS37622-90-5
MFC6H8N2O2
MW140.14
EINECS609-452-9
MOL File37622-90-5.mol

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.
pka	11.70±0.50(Predicted)
form	Crystalline Powder
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
Storage Class	11 - Combustible Solids
Hazard Classifications	Eye Irrit. 2 Skin Irrit. 2 STOT SE 3

MSDS

Provider	Language
SigmaAldrich	English
ALFA	English

Usage And Synthesis

Chemical Properties

White to pale yellow crystalline powder

Uses

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

Uses

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

Synthesis Reference(s)

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

Synthesis

Propanoicacid,2-formyl-3-oxo-,ethylester

80370-42-9

37622-90-5

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

Chemical Properties

Safety Information

MSDS

Usage And Synthesis

Preparation Products And Raw materials

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