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1H-Imidazole-5-acetonitrile
[CAS# 18502-05-1]

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Identification
Classification Organic raw materials >> Heterocyclic compound >> Imidazoles
Name 1H-Imidazole-5-acetonitrile
Synonyms 4(5)-Cyanomethylimidazole
Molecular Structure CAS # 18502-05-1, 1H-Imidazole-5-acetonitrile, 4(5)-Cyanomethylimidazole
Molecular Formula C5H5N3
Molecular Weight 107.11
CAS Registry Number 18502-05-1
EC Number 677-882-4
SMILES C1=C(NC=N1)CC#N
Properties
Density 1.2±0.1 g/cm3, Calc.*
Melting point 142 ºC
Index of Refraction 1.561, Calc.*
Boiling Point 393.6±17.0 ºC (760 mmHg), Calc.*
Flash Point 132.1±6.1 ºC, Calc.*
* Calculated using Advanced Chemistry Development (ACD/Labs) Software.
Safety Data
Hazard Symbols symbol symbol   GHS06;GHS07 Danger    Details
Hazard Statements H301+H311+H331-H301-H311-H315-H319-H331-H335    Details
Precautionary Statements P261-P262-P264-P264+P265-P270-P271-P280-P301+P316-P302+P352-P304+P340-P305+P351+P338-P316-P319-P321-P330-P332+P317-P337+P317-P361+P364-P362+P364-P403+P233-P405-P501    Details
Hazard Classification
up    Details
HazardClassCategory CodeHazard Statement
Skin irritationSkin Irrit.2H315
Acute toxicityAcute Tox.3H301
Acute toxicityAcute Tox.3H311
Acute toxicityAcute Tox.3H331
Specific target organ toxicity - single exposureSTOT SE3H335
Eye irritationEye Irrit.2H319
Eye irritationEye Irrit.2AH319
SDS Available
up Discovory and Applicatios
1H-Imidazole-5-acetonitrile is a heterocyclic organic compound featuring an imidazole ring with an acetonitrile functional group. Its molecular formula is C5H6N4, and it is recognized for its significant applications in various fields, including medicinal chemistry and organic synthesis. The compound’s unique structure, characterized by the imidazole moiety, contributes to its diverse biological activities and utility in chemical reactions.

The discovery of 1H-imidazole-5-acetonitrile is rooted in the broader exploration of imidazole derivatives. Imidazole itself, a five-membered ring containing two nitrogen atoms, has been extensively studied since its first synthesis in the early 19th century. Subsequent research focused on functionalizing the imidazole ring to enhance its chemical properties and expand its potential applications. The introduction of the acetonitrile group to the 5-position of the imidazole ring led to the identification of 1H-imidazole-5-acetonitrile as a novel compound with promising features.

1H-Imidazole-5-acetonitrile has garnered considerable attention in medicinal chemistry due to its pharmacological properties. Research has indicated that this compound exhibits notable activity against various biological targets, making it a valuable candidate in drug discovery. Its structure allows for interactions with enzymes and receptors, and studies have shown its potential as an anticancer agent, antifungal agent, and antimicrobial agent. The ability to modify the acetonitrile group further enhances its versatility, allowing chemists to explore derivatives with improved efficacy and selectivity.

In addition to its medicinal applications, 1H-imidazole-5-acetonitrile serves as an important intermediate in organic synthesis. It is utilized in the preparation of various pharmaceuticals and agrochemicals. The compound's reactivity allows it to participate in numerous chemical reactions, including nucleophilic substitutions and cyclization processes. This makes it a valuable building block for synthesizing more complex molecules. The exploration of 1H-imidazole-5-acetonitrile in synthetic pathways has led to the development of new compounds with diverse functionalities.

Moreover, the compound is of interest in materials science, particularly in the development of functionalized polymers and catalysts. Its unique chemical properties allow for its incorporation into polymeric systems, resulting in materials with enhanced performance characteristics. Research into the catalytic applications of 1H-imidazole-5-acetonitrile has revealed its potential in facilitating various chemical transformations, further expanding its utility in the field of organic chemistry.

The environmental profile of 1H-imidazole-5-acetonitrile has also been a subject of investigation. As sustainability becomes increasingly important in chemical manufacturing, the potential for this compound to serve as a green alternative in synthetic processes is being explored. The biodegradability and low toxicity of imidazole derivatives suggest their suitability for use in eco-friendly formulations.

In conclusion, 1H-imidazole-5-acetonitrile is a versatile compound with a rich history of discovery and application. Its unique structure imparts significant biological activity, making it a valuable target in drug development. Furthermore, its utility as an intermediate in organic synthesis and potential applications in materials science highlight its importance in contemporary chemistry. Ongoing research continues to uncover new possibilities for this compound, ensuring its relevance in various scientific fields.
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