1-PHENYL-1H-PYRAZOLE-4-CARBALDEHYDE Chemical Properties

Melting point:

84-88 °C

Boiling point:

312.7±15.0 °C(Predicted)

Density 

1.15±0.1 g/cm3(Predicted)

storage temp. 

under inert gas (nitrogen or Argon) at 2–8 °C

solubility 

soluble in Toluene

pka

-2.57±0.10(Predicted)

form 

Solid

color 

Pale yellow

Sensitive 

Moisture & Light Sensitive

InChI

InChI=1S/C10H8N2O/c13-8-9-6-11-12(7-9)10-4-2-1-3-5-10/h1-8H

InChIKey

PHVRLPFVPVKYOI-UHFFFAOYSA-N

SMILES

N1(C2=CC=CC=C2)C=C(C=O)C=N1

CAS DataBase Reference

54605-72-0(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38-20/21/22

Safety Statements 

26-37/39-36/37-3/7

WGK Germany 

3

HazardClass 

IRRITANT

HS Code 

29339900

1-PHENYL-1H-PYRAZOLE-4-CARBALDEHYDE Usage And Synthesis

Chemical Properties

White crystal

Uses

1-Phenylpyrazole-4-carboxaldehyde is used to synthesize phenyl-pyrazolyl acrylic acid benzylidene carbohydrazide derivatives with antichagasic activities. It is also used to prepare ORL1 receptor antagonists.

Synthesis

1) Add 7.3 g (0.1 mmol) of N,N-dimethylformamide (DMF) to a 250 mL three-necked flask and cool in an ice water bath with stirring. 15.4 g (0.1 mmol) of phosphorus triclosan was slowly added dropwise and stirring was continued for 1 hour after completion of the drop. Subsequently, 2.88 g (0.02 mmol) of 1-phenylpyrazole was added and the reaction was heated to 100°C and refluxed for 3-6 h. The reaction was monitored by TLC.2) Upon completion of the reaction, the reaction mixture was poured into ice-water and the pH was adjusted to neutral with sodium carbonate solution. It was extracted with ethyl acetate (3 x 50 mL), and the combined organic phases were washed with 50 mL of saturated brine.3) The organic phase was purified by column chromatography (the eluent was a solvent mixture of ethyl acetate and petroleum ether (60-90°C), 1:5, v/v/v), and was concentrated under reduced pressure to give 3.10 g of the white solid product, 1-phenyl-1H-pyrazole-4-carbaldehyde, in 90.0% yield.

References

[1] Patent: CN107964007, 2018, A. Location in patent: Paragraph 0498
[2] Bioorganic and Medicinal Chemistry, 2009, vol. 17, # 1, p. 295 - 302
[3] Journal of Heterocyclic Chemistry, 1993, vol. 30, # 4, p. 957 - 960
[4] Patent: US2006/34786, 2006, A1. Location in patent: Page/Page column 62
[5] Synthetic Communications, 1998, vol. 28, # 7, p. 1299 - 1321

1-PHENYL-1H-PYRAZOLE-4-CARBALDEHYDE(54605-72-0)Related Product Information

• 4-ACETYL-5-METHYL-1-PHENYLPYRAZOLE
• 5-AMINO-1-PHENYLPYRAZOLE-4-CARBOXAMIDE
• 1-PHENYL-5-PROPYL-1H-PYRAZOLE-4-CARBOXYLIC ACID
• 5-AMINO-4-CARBETHOXY-1-PHENYLPYRAZOLE
• 1-(4-CHLOROPHENYL)-5-PROPYL-1H-PYRAZOLE-4-CARBOXYLIC ACID
• 1-PHENYL-5-(TRIFLUOROMETHYL)-1H-PYRAZOLE-4-CARBOHYDRAZIDE
• 5-METHYL-1-PHENYL-1H-PYRAZOLE-4-CARBOXYLIC ACID
• 2-(4-CHLOROPHENYL)-3-(TRIFLUOROMETHYL)PYRAZOLE-4-CARBONYL CHLORIDE
• ETHYL 5-METHYL-1-PHENYL-1H-PYRAZOLE-4-CARBOXYLATE
• 3,5-DIMETHYL-1-PHENYL-1H-PYRAZOLE-4-CARBALDEHYDE
• 1-PHENYL-5-(TRIFLUOROMETHYL)PYRAZOLE-4-CARBONYL CHLORIDE
• ETHYL 2-PHENYL-3-(TRIFLUOROMETHYL)PYRAZOLE-4-CARBOXYLATE
• 5-METHYL-1-PHENYL-1H-PYRAZOLE-4-CARBALDEHYDE
• 3-PHENYL-1H-PYRAZOLE-4-CARBALDEHYDE
• 3-P-TOLYL-1H-PYRAZOLE-4-CARBOXALDEHYDE
• 1-PHENYL-1H-PYRAZOLE-5-CARBALDEHYDE
• 1-(3-Fluoro-phenyl)-1H-pyrazole-4-carbaldehyde
• 2-METHYL-5-PHENYL-2H-PYRAZOLE-3-CARBALDEHYDE