3-PHENYL-1H-PYRAZOLE-5-CARBOXYLIC ACID

3-PHENYL-1H-PYRAZOLE-5-CARBOXYLIC ACID Property

Melting point:

238-242 °C (dec.)(lit.)

Boiling point:

496.5±33.0 °C(Predicted)

Density 

1.355±0.06 g/cm3 (20 ºC 760 Torr)

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

form 

powder to crystal

pka

3.92±0.10(Predicted)

color 

White to Light yellow to Light orange

InChI

InChI=1S/C10H8N2O2/c13-10(14)9-6-8(11-12-9)7-4-2-1-3-5-7/h1-6H,(H,11,12)(H,13,14)

InChIKey

QBPUOAJBMXXBNU-UHFFFAOYSA-N

SMILES

N1C(C2=CC=CC=C2)=CC(C(O)=O)=N1

Safety

Hazard Codes 

Xi,Xn

Risk Statements 

36/37/38-22

Safety Statements 

26-36

WGK Germany 

3

RTECS 

UQ6437000

HazardClass 

IRRITANT

HS Code 

2933199090

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H315Causes skin irritation

H319Causes serious eye irritation

Precautionary statements

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

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.

P332+P313IF SKIN irritation occurs: Get medical advice/attention.

P337+P313IF eye irritation persists: Get medical advice/attention.

3-PHENYL-1H-PYRAZOLE-5-CARBOXYLIC ACID Chemical Properties,Usage,Production

Definition

ChEBI: 3-phenyl-1H-pyrazole-5-carboxylic acid is a ring assembly and a member of pyrazoles.

Synthesis

General procedure for the synthesis of 5-phenyl-1H-pyrazole-3-carboxylic acid from ethyl 5-phenylpyrazole-3-carboxylate: to a solution of ethyl 5-phenylpyrazole-3-carboxylate (3.4 g, 15.9 mmol) in methanol (40 mL) was added an aqueous sodium hydroxide solution (140 mL, 4 M). The reaction mixture was stirred at room temperature for 2 hours. The reaction mixture was concentrated under reduced pressure to remove methanol. The aqueous phase was acidified to pH=3 with aqueous hydrochloric acid (1M) and extracted with ethyl acetate. The organic phase was dried with anhydrous sodium sulfate, filtered and concentrated to give the crude product. The crude product was purified by silica gel column chromatography, and the target compound 5-phenyl-1H-pyrazole-3-carboxylic acid (2.4 g, 80.4% yield) was obtained after elution. Mass spectrum (ESI) m/z: 189.1 [M+H]+.

References

[1] Journal of Medicinal Chemistry, 2003, vol. 46, # 18, p. 3945 - 3951
[2] Patent: US2018/271846, 2018, A1. Location in patent: Paragraph 0101; 0116; 0117
[3] New Journal of Chemistry, 2011, vol. 35, # 4, p. 865 - 875
[4] Bioorganic and Medicinal Chemistry, 2014, vol. 22, # 21, p. 6209 - 6219