1H-Imidazole-4-carbaldehyde
[CAS# 3034-50-2]

Identification

• Classification: Organic raw materials >> Aldehyde
• Name: 1H-Imidazole-4-carbaldehyde
• Synonyms: 4-Imidazolecarboxaldehyde
• Molecular Formula: C₄H₄N₂O
• Molecular Weight: 96.09
• CAS Registry Number: 3034-50-2
• EC Number: 221-227-3
• SMILES: C1=C(NC=N1)C=O

Properties

• Density: 1.3±0.1 g/cm³ Calc.^*
• Melting point: 174 - 177 °C (Expl.)
• Boiling point: 367.8±15.0 °C 760 mmHg (Calc.)^*
• Flash point: 179.8±26.8 °C (Calc.)^*
• Index of refraction: 1.62 (Calc.)^*

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software.

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H315-H319-H335
• Safety Statements: P261-P264-P264+P265-P271-P280-P302+P352-P304+P340-P305+P351+P338-P319-P321-P332+P317-P337+P317-P362+P364-P403+P233-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Skin irritation	Skin Irrit.	2	H315
Specific target organ toxicity - single exposure	STOT SE	3	H335
Eye irritation	Eye Irrit.	2	H319
Acute toxicity	Acute Tox.	4	H302
Acute toxicity	Acute Tox.	4	H332
Acute toxicity	Acute Tox.	4	H312
Eye irritation	Eye Irrit.	2A	H319

Discovery and Applications

1H-Imidazole-4-carbaldehyde is a heterocyclic organic compound characterized by an imidazole ring substituted with an aldehyde functional group at the 4-position. The imidazole ring is a five-membered aromatic structure containing two nitrogen atoms at positions 1 and 3. This compound belongs to the class of imidazole derivatives, which are important scaffolds in medicinal chemistry and organic synthesis due to their biological activity and versatile chemical reactivity.

The discovery of 1H-imidazole-4-carbaldehyde is rooted in the exploration of imidazole derivatives, which have been widely studied for their role in various biological systems, including enzyme catalysis and signaling. The presence of the aldehyde group introduces a reactive site that allows further chemical modifications, making it a valuable intermediate in the synthesis of pharmaceuticals, agrochemicals, and other biologically active molecules.

In practical applications, 1H-imidazole-4-carbaldehyde serves as a building block for the synthesis of imidazole-based compounds. It is used in the preparation of Schiff bases through condensation reactions with amines, yielding imines that exhibit diverse biological activities such as antimicrobial, antifungal, and anticancer properties. These derivatives are important in drug discovery and development due to their ability to interact with various biological targets.

Furthermore, the compound is employed in coordination chemistry, where the imidazole nitrogen atoms can bind to metal centers, forming complexes with potential catalytic and therapeutic applications. Its aldehyde functionality can participate in condensation, reduction, and other organic transformations, making it a versatile reagent in synthetic chemistry.

1H-Imidazole-4-carbaldehyde has also been utilized in the design of enzyme inhibitors, where the imidazole ring mimics histidine residues in enzyme active sites, providing specificity and binding affinity. This feature has been exploited in the development of inhibitors for various enzymes implicated in disease pathways.

Overall, 1H-imidazole-4-carbaldehyde is a significant compound in chemical and pharmaceutical research, primarily due to its structural features that facilitate diverse chemical modifications and biological applications. Its role as a synthetic intermediate continues to contribute to the advancement of medicinal chemistry and the development of novel therapeutic agents.

References

2015. Reactions of 2-aminothiophenol with pyridineand imidazolecarboxaldehydes. Russian Chemical Bulletin, 64(8).
DOI: 10.1007/s11172-015-1103-3

2016. Concise Synthesis of Anserine: Efficient Solvent Tuning in Asymmetric Hydrogenation Reaction. Synlett, 27(20).
DOI: 10.1055/s-0035-1562796

2020. Iodine-mediated aminohalogenation-oxidation to synthesize 2-fluoroalkyl imidazole derivatives. Chemical Papers, 74(12).
DOI: 10.1007/s11696-020-01360-6