1,3-Dimethyl-5-pyrazolone Chemical Properties

Melting point:

117°C

Boiling point:

210.05°C (rough estimate)

Density 

1.1524 (rough estimate)

refractive index 

1.4730 (estimate)

storage temp. 

Sealed in dry,Room Temperature

solubility 

Chloroform (Slightly), DMSO (Slightly), Ethyl Acetate (Slightly, Sonicated), Met

form 

Solid

pka

2.93±0.50(Predicted)

color 

Off-White to Light Beige

Water Solubility 

almost transparency

InChI

InChI=1S/C5H8N2O/c1-4-3-5(8)7(2)6-4/h3H2,1-2H3

InChIKey

JXPVQFCUIAKFLT-UHFFFAOYSA-N

SMILES

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

CAS DataBase Reference

2749-59-9(CAS DataBase Reference)

NIST Chemistry Reference

3H-Pyrazol-3-one, 2,4-dihydro-2,5-dimethyl-(2749-59-9)

EPA Substance Registry System

3H-Pyrazol-3-one, 2,4-dihydro-2,5-dimethyl- (2749-59-9)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36/37/39

Hazard Note 

Irritant

HS Code 

2933199090

MSDS

• Language:English Provider:1,3-Dimethyl-5-pyrazolone

1,3-Dimethyl-5-pyrazolone Usage And Synthesis

Chemical Properties

Light Beige Solid

Uses

1,3-Dimethyl-5-pyrazolone (cas# 2749-59-9) is a compound useful in organic synthesis.

Synthesis

Methylhydrazine (4.47 mL, 84.99 mmol) was added slowly and dropwise to a solution of ethyl 3-oxohexanoate (11.06 g, 84.99 mmol) in anhydrous ethanol (100 mL) at 0 °C. The reaction system was naturally warmed to room temperature with continuous stirring for 3.5 hours. Subsequently, the reaction mixture was heated to 60 °C and the reaction was continued for 10 hours and kept at reflux for 2.5 hours. Upon completion of the reaction, the mixture was concentrated to dryness using a rotary evaporator to afford intermediate 4 as a viscous pink solid (9.52 g, 100% yield). The structure of intermediate 4 was confirmed by 1H NMR (400 MHz, CDCl3) and mass spectrometry (ESI): 1H NMR (400 MHz, CDCl3) δ (ppm): 5.06 (s, 1H), 3.85 (bs, 1H), 3.32 (s, 3H), 1.94 (s, 3H); MS (ESI): m/z calculated value ( C15H9N2O) was 113.1 and the measured value was 113.2 ([M+H]+).

References

[1] Bioorganic and Medicinal Chemistry Letters, 2005, vol. 15, # 13, p. 3307 - 3312
[2] Patent: WO2016/205460, 2016, A1. Location in patent: Paragraph 0140-0141
[3] Patent: WO2016/7905, 2016, A1. Location in patent: Page/Page column 37
[4] Bioorganic and Medicinal Chemistry Letters, 2016, vol. 26, # 23, p. 5815 - 5818
[5] Patent: US4382948, 1983, A

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