5-(tert-Butyl)-1H-imidazole-4-carbaldehyde Chemical Properties

Boiling point:

338.9±30.0 °C(Predicted)

Density 

1.092±0.06 g/cm3(Predicted)

storage temp. 

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

pka

11.53±0.10(Predicted)

form 

solid

color 

Off-white

InChI

InChI=1S/C8H12N2O/c1-8(2,3)7-6(4-11)9-5-10-7/h4-5H,1-3H3,(H,9,10)

InChIKey

FSTXHTKEZGSDNN-UHFFFAOYSA-N

SMILES

C1NC(C=O)=C(C(C)(C)C)N=1

Safety Information

HS Code 

2933998090

5-(tert-Butyl)-1H-imidazole-4-carbaldehyde Usage And Synthesis

Synthesis

General procedure for the synthesis of 5-(tert-butyl)-1H-imidazole-4-carbaldehyde from (5-tert-butyl-1H-imidazol-4-yl)methanol: 50 g (324 mmol) of 5-(tert-butyl)-1H-imidazole-4-methanol was dissolved in 500 mL of dichloromethane, and 282 g (3242 mmol) of manganese dioxide was added as oxidizer. The reaction mixture was stirred at room temperature for 24 hours to complete the oxidation reaction. Upon completion of the reaction, solid impurities were removed by filtration with the aid of diatomaceous earth. The filter cake was washed three times (500 mL each) with anhydrous ethanol to remove residual reactants and by-products. Finally, the filtrate was concentrated under reduced pressure to give 43 g of a light yellow solid product, 5-(tert-butyl)-1H-imidazole-4-carbaldehyde, in 87% yield.

References

[1] Patent: CN107011331, 2017, A. Location in patent: Paragraph 0045; 0046
[2] Patent: CN107011322, 2017, A. Location in patent: Paragraph 0026; 0029
[3] Journal of Medicinal Chemistry, 2012, vol. 55, # 3, p. 1056 - 1071
[4] Bioorganic and Medicinal Chemistry Letters, 2017, vol. 27, # 6, p. 1416 - 1419

5-(tert-Butyl)-1H-imidazole-4-carbaldehyde(714273-83-3)Related Product Information

• tert-Butyl methyl ether