1-METHYL-1H-IMIDAZOLE-4-CARBALDEHYDE Chemical Properties

Melting point:

68-69℃

Boiling point:

300.1±15.0 °C(Predicted)

Density 

1.14±0.1 g/cm3(Predicted)

storage temp. 

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

solubility 

Chloroform (Slightly), Methanol (Slightly, Sonicated)

form 

Solid

pka

2.94±0.61(Predicted)

color 

Yellow to Dark Yellow

InChI

InChI=1S/C5H6N2O/c1-7-2-5(3-8)6-4-7/h2-4H,1H3

InChIKey

CQZXDIHVSPZIGF-UHFFFAOYSA-N

SMILES

C1N(C)C=C(C=O)N=1

Safety Information

Hazard Codes 

Xi,Xn

Risk Statements 

22-36/37/38

Safety Statements 

22-26-36/37/39

Hazard Note 

Irritant

HS Code 

2933299090

1-METHYL-1H-IMIDAZOLE-4-CARBALDEHYDE Usage And Synthesis

Uses

1-Methyl-1H-imidazole-4-carbaldehyde (cas# 17289-26-8) was identified in the methanolic extract of red Vitis Vinifera peel.

Synthesis

General procedure for the synthesis of 1-methyl-1H-imidazole-4-carboxaldehyde: (1-methyl-1H-imidazol-4-yl)methanol (5 g, 44.6 mmol) was dissolved in acetone (50 mL) under nitrogen protection and manganese dioxide (19.38 g, 223 mmol) was added slowly. The reaction mixture was stirred at 60°C for 12 hours. After completion of the reaction, the solid was removed by filtration and the filtrate was concentrated to afford the crude product 1-methyl-1H-imidazole-4-carbaldehyde (4.12 g, 34.4 mmol, 77% yield), which could be used in the subsequent reaction without further purification. m/z 111.2 ([M+H]+) and retention time 0.49 min were obtained by LC-MS analysis.

References

[1] Patent: WO2017/60854, 2017, A1. Location in patent: Page/Page column 475
[2] Journal of Medicinal Chemistry, 2007, vol. 50, # 19, p. 4728 - 4745

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