2H-PYRAZOLE-3-CARBALDEHYDE Chemical Properties

Melting point:

149.0 to 153.0 °C

Boiling point:

300.0±13.0 °C(Predicted)

Density 

1.323

storage temp. 

Inert atmosphere,Room Temperature

form 

powder to crystal

pka

11.20±0.10(Predicted)

color 

White to Orange to Green

InChI

InChI=1S/C4H4N2O/c7-3-4-1-2-5-6-4/h1-3H,(H,5,6)

InChIKey

ICFGFAUMBISMLR-UHFFFAOYSA-N

SMILES

N1C=CC(C=O)=N1

CAS DataBase Reference

3920-50-1(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi,Xn

Risk Statements 

22-37/38-41

Safety Statements 

26-36/39

WGK Germany 

3

HazardClass 

IRRITANT

HS Code 

2933119000

2H-PYRAZOLE-3-CARBALDEHYDE Usage And Synthesis

Chemical Properties

Colorless Solid

Uses

1H-?Pyrazole-?3-?carboxaldehyde is an intermediate used to prepare fused pyrrole carboxylic acids as novel, potent D-?amino acid oxidase (DAO) inhibitors. It is also a building block to synthesize α-?substituted benzylidenemalononitrile tyrphostins as potent inhibitors of EGF receptor and ErbB2?/neu tyrosine kinases.

Synthesis

The general procedure for the synthesis of 3-pyrazolecarboxaldehyde from 3-dimethoxymethyl-1H-pyrazole: 2.3 kg of formic acid was added slowly and dropwise to 15.5 kg of an aqueous solution containing 13.8 kg of 3-dimethoxymethyl-1H-pyrazole at 0-15 °C. Subsequently, the reaction mixture was magnetically stirred at 25 °C for 12 h. A light yellow solid was obtained upon completion of the reaction. The precipitate was separated by filtration and the filter cake was washed with 10 L of water to give 643 g of the final yellow solid product 3-pyrazolecarboxaldehyde.

References

[1] Journal of Organic Chemistry, 2007, vol. 72, # 15, p. 5890 - 5893
[2] Chinese Journal of Catalysis, 2016, vol. 37, # 9, p. 1446 - 1450
[3] European Journal of Medicinal Chemistry, 1993, vol. 28, # 2, p. 129 - 140
[4] Patent: CN107235982, 2017, A. Location in patent: Paragraph 0008

2H-PYRAZOLE-3-CARBALDEHYDE(3920-50-1)Related Product Information

• 4-Nitropyrazole-3-carboxylic acid
• 1-(TERT-BUTYL)-3-METHYL-1H-PYRAZOLE-5-CARBOXYLIC ACID
• 1-(TERT-BUTYL)-3-METHYL-1H-PYRAZOLE-5-CARBONYL CHLORIDE
• 5-Methyl-1H-pyrazole-3-carboxylic acid
• 1-BENZYL-3-(TERT-BUTYL)-1H-PYRAZOLE-5-CARBONYL CHLORIDE
• Pyrazofurin
• Ethyl 3-methyl-1H-pyrazole-5-carboxylate
• ETHYL 1,5-DIMETHYL-1H-PYRAZOLE-3-CARBOXYLATE
• 1,4-DIHYDRO-3-BETA-D-RIBOFURANOSYL-7H-PYRAZOLO[4,3-D]PYRIMIDIN-7-ONE
• 3,5-PYRAZOLEDICARBOXYLIC ACID
• 3-(TERT-BUTYL)-1-METHYL-1H-PYRAZOLE-5-CARBONYL CHLORIDE
• 5-Pyrazolecarboxylic acid
• 5-METHYL-1 H-PYRAZOLE-3-CARBOXYLIC ACID HYDRAZIDE
• 5-Methyl-1H-pyrazole-4-carbaldehyde
• 1-PHENYL-1H-PYRAZOLE-5-CARBALDEHYDE
• 3-CYCLOPROPYL-1-METHYL-1H-PYRAZOLE-4-CARBALDEHYDE
• 1,5-DIMETHYL-1H-PYRAZOLE-4-CARBALDEHYDE
• 3-PHENYL-1H-PYRAZOLE-4-CARBALDEHYDE