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

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

Melting point:

180～182℃

Boiling point:

422.0±33.0 °C(Predicted)

Density 

1.1085 g/cm3(Temp: 19.1 °C)

storage temp. 

2-8°C

pka

10.56±0.10(Predicted)

InChI

InChI=1S/C11H10N2O2/c1-15-11(14)10-7-9(12-13-10)8-5-3-2-4-6-8/h2-7H,1H3,(H,12,13)

InChIKey

ROXAFVODFXYSFO-UHFFFAOYSA-N

SMILES

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

Safety

Hazard Codes 

Xi

HS Code 

2933199090

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

P271Use only outdoors or in a well-ventilated area.

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

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

Synthesis

General procedure for the synthesis of methyl 5-phenylpyrazole-3-carboxylate from methyl 2,4-dioxo-4-phenylbutanoate: methyl 2,4-dioxo-4-phenylbutanoate (470 mg, 2.28 mmol) was dissolved in acetic acid (5 mL), followed by the addition of hydrazine hydrate (122 μL, 2.51 mmol). The reaction mixture was heated at reflux for 2 h at 118 °C. Upon completion of the reaction, the mixture was concentrated under vacuum to afford methyl 5-phenylpyrazole-3-carboxylate (320 mg, 69% yield), the product was a yellow solid.LCMS analysis result: ES+ 203.0 [MH]+.

References

[1] Patent: WO2014/20350, 2014, A1. Location in patent: Page/Page column 51
[2] Patent: WO2014/20351, 2014, A1. Location in patent: Page/Page column 36
[3] Journal of Medicinal Chemistry, 1998, vol. 41, # 13, p. 2390 - 2410
[4] Bioorganic and Medicinal Chemistry Letters, 2013, vol. 23, # 1, p. 273 - 280
[5] Patent: US2013/143870, 2013, A1. Location in patent: Paragraph 0547; 0548