Imidazole-2-carboxaldehyde Chemical Properties

Melting point:

209 °C (dec.) (lit.)

Boiling point:

296.5±23.0 °C(Predicted)

Density 

1.322±0.06 g/cm3(Predicted)

storage temp. 

Keep in dark place,Inert atmosphere,Room temperature

solubility 

DMSO (Sparingly), Methanol (Slightly, Sonicated)

form 

Solid

pka

11.48±0.10(Predicted)

color 

Light Brown to Brown

Water Solubility 

Soluble in water.

Sensitive 

Air Sensitive

BRN 

4371302

InChI

InChI=1S/C4H4N2O/c7-3-4-5-1-2-6-4/h1-3H,(H,5,6)

InChIKey

XYHKNCXZYYTLRG-UHFFFAOYSA-N

SMILES

C1(C=O)NC=CN=1

CAS DataBase Reference

10111-08-7(CAS DataBase Reference)

NIST Chemistry Reference

1H-imidazole-2-carboxaldehyde(10111-08-7)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36-36/37/39-3

WGK Germany 

3

F 

10

HazardClass 

IRRITANT

HS Code 

29332900

MSDS

• Language:English Provider:SigmaAldrich
• Language:English Provider:ALFA

Imidazole-2-carboxaldehyde Usage And Synthesis

Chemical Properties

White to light brown solid

Uses

Imidazole-2-carboxaldehyde is a novel protein tyrosine phosphatase 1B (PTP1B) inhibitor with an important application to treat type-2 diabetes. It is used in the preparation of tridentate Schiff-base carboxylate-containing ligands by undergoing condensation reaction with amino acids beta-alanine and 2-aminobenzoic acid. It is also involved in the study of the imidazole-directed allylation of aldimines.

Uses

1H-Imidazole-2-carboxaldehyde is a novel PTP1b inhibitor with potential application to treat type 2 diabetes.

Uses

Used in a study of the imidazole-directed allylation of aldimines.1

Synthesis Reference(s)

Organic Syntheses, Coll. Vol. 7, p. 287, 1990
The Journal of Organic Chemistry, 60, p. 1090, 1995 DOI: 10.1021/jo00109a052

Synthesis

To a solution of 2-bromo-1H-imidazole (0.65 g, 4.4 mmol, 1.0 eq.) in anhydrous THF (20 mL) was slowly added a solution of 2 M i-PrMgCl in THF (2.2 mL, 4.4 mmol, 1.0 eq.) over 5 min at 0 °C. The reaction mixture was continued to be stirred at this temperature for 5 min. Subsequently, a hexane solution of 2.5 M n-BuLi (3.5 mL, 8.8 mmol, 2.0 eq.) was added dropwise over 5 min while the reaction temperature was controlled below 20 °C. After dropwise addition, the reaction mixture was stirred at this temperature for 30 min. Then, dry N,N-dimethylformamide (DMF, 0.32 g, 4.4 mmol, 1.0 eq.) was added and the reaction mixture was slowly warmed up to 20 °C over 0.5 h. The reaction was completed with the addition of 6 mL of N,N-dimethylformamide. Upon completion of the reaction, the reaction was quenched with 6 mL of water, kept below 20 °C and stirred for 10 min. The organic and aqueous phases were separated and the aqueous phase was extracted once with ethyl acetate (10 mL). The organic phases were combined, and the resulting suspension was returned to room temperature, filtered through a silica gel pad (0.5 cm × 1 cm), and eluted with 10 mL of ethyl acetate. The filtrate was concentrated and the residue was purified by rapid chromatography on silica gel (eluent: petroleum ether/ethyl acetate = 10:1) to afford 2-imidazolecarboxaldehyde (3k) as a light yellow solid with a yield of 0.38 g (91% yield) and a melting point of 205-206 °C. 1H-NMR (600 MHz, DMSO-d6) δ 13.60 (s, 1H), 9.64 (s, 1H) , 7.42 (s, 2H).13C-NMR (151 MHz, DMSO-d6) δ 181.66, 146.09.

References

[1] Molecules, 2017, vol. 22, # 11,

Imidazole-2-carboxaldehyde(10111-08-7)Related Product Information

• 2-Methylimidazole
• Methimazole
• Levamisole hydrochloride
• Formaldehyde
• Levamisole
• Mebendazole
• 1H-Imidazole-2-carboxylic acid
• Imidazole
• 4,5-Imidazoledicarboxylic acid
• 1H-Imidazol-2-carboxamide
• (1H-IMIDAZOL-2-YL)-METHANOL
• 3,5-DIMETHANOLPYRIDINE
• Ethanone, 1-imidazo[1,2-a]pyridin-3-yl- (9CI)
• 2-Benzimidazolecarboxylic acid
• 1H-Benzimidazole-2-carboxaldehyde
• Midazolam
• 1-METHYL-2-FORMYLBENZIMIDAZOLE
• IMIDAZOLE-4-CARBOXALDEHYDE,1H-IMIDAZOLE-4-CARBOXALDEHYDE