4-(1H-Imidazol-1-yl)benzaldehyde Chemical Properties

Melting point:

153-155 °C(lit.)

Boiling point:

351.1±25.0 °C(Predicted)

Density 

1.15±0.1 g/cm3(Predicted)

storage temp. 

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

solubility 

soluble in Methanol

form 

powder to crystal

pka

5.07±0.10(Predicted)

color 

Light yellow to Yellow to Orange

InChI

InChI=1S/C10H8N2O/c13-7-9-1-3-10(4-2-9)12-6-5-11-8-12/h1-8H

InChIKey

DCICUQFMCRPKHZ-UHFFFAOYSA-N

SMILES

C(=O)C1=CC=C(N2C=NC=C2)C=C1

CAS DataBase Reference

10040-98-9(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36

WGK Germany 

3

HazardClass 

IRRITANT

HS Code 

29332900

MSDS

• Language:English Provider:SigmaAldrich

4-(1H-Imidazol-1-yl)benzaldehyde Usage And Synthesis

Chemical Properties

White to light brown solid

Uses

4-(1H-Imidazol-1-yl)benzaldehyde could be used to synthesis (E)-3-[4-(1H-imidazol-1-yl)phenyl]-1-(4-methylphenyl)prop-2-en-1-one with 4′-methylacetophenone through Claisen–Schmidt condensation. This novel compound is suitable for anti-aspergillus activity study[1].

Synthesis

General procedure for the synthesis of 4-(imidazol-1-yl)benzaldehyde from imidazole and p-fluorobenzaldehyde: A mixture of p-fluorobenzaldehyde (25.0 g, 0.200 mol), imidazole (0.300 mol), and anhydrous potassium carbonate (40.0 g) was dissolved in DMF (300 mL) under dry conditions, and catalytic amount of Aliquat 336 reagent was added. The reaction mixture was refluxed at 100 °C for 24 hours. Upon completion of the reaction, the reaction mixture was concentrated under reduced pressure and cooled to room temperature. Subsequently, the concentrate was poured into ice water and allowed to stand overnight. The precipitated solid product was filtered, washed with water and recrystallized with methanol to afford the target compound 4-(1H-imidazol-1-yl)benzaldehyde (Ia) in 92% yield as yellow crystals with a melting point of 152°C (in agreement with literature reports) [34,44].

References

[1] N. Bailey, Bradley O. Ashburn. “(E)-3-[4-(1H-Imidazol-1-yl)phenyl]-1-(4-methylphenyl)prop-2-en-1-one.” Molbank 1 1 (2021).

4-(1H-Imidazol-1-yl)benzaldehyde(10040-98-9)Related Product Information

• 1H-Imidazole-4-carbaldehyde
• 4-Hydroxybenzaldehyde
• Benzaldehyde
• p-Anisaldehyde
• Imidazole
• 4-Dimethylaminobenzaldehyde
• 4-(1H-imidazol-1-yl)pyridine
• sodium benzaldehyde-o-sulfonate
• 4-(1H-IMIDAZOL-1-YL)BENZOIC ACID
• 4'-(IMIDAZOL-1-YL)ACETOPHENONE
• 2-IMIDAZOL-1-YL-BENZALDEHYDE, 95+%,2-IMIDAZOL-1-YL-BENZALDEHYDE
• 3-METHOXY-4-(4-METHYL-1H-IMIDAZOL-1-YL)BENZALDEHYDE,3-METHOXY-4-(4-METHYL-IMIDAZOL-1-YL)-BENZALDEHYDE
• Formaldehyde
• 1-[4-(4,5-DICHLORO-1H-IMIDAZOL-1-YL)PHENYL]ETHAN-1-ONE
• GLG-V 13
• METHYL 4-(1H-IMIDAZOL-1-YL)BENZENECARBOXYLATE
• BIS[4-(1H-IMIDAZOL-1-YL)PHENYL]METHANONE
• 3-DIMETHYLAMINO-1-(4-IMIDAZOL-1-YL-PHENYL)-PROPENONE