1-PHENYL-1H-PYRAZOLE-4-CARBALDEHYDE

1-PHENYL-1H-PYRAZOLE-4-CARBALDEHYDE Property

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

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

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P271Use only outdoors or in a well-ventilated area.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P302+P352IF ON SKIN: wash with plenty of soap and water.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

1-PHENYL-1H-PYRAZOLE-4-CARBALDEHYDE Chemical Properties,Usage,Production

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