2-Ethyl-4-methyl-1H-imidazole-1-propanenitrile
[CAS# 23996-25-0]

Identification

• Classification: Organic raw materials >> Heterocyclic compound >> Imidazoles
• Name: 2-Ethyl-4-methyl-1H-imidazole-1-propanenitrile
• Synonyms: 3-(2-ethyl-4-methylimidazol-1-yl)propanenitrile
• Molecular Formula: C₉H₁₃N₃
• Molecular Weight: 163.22
• CAS Registry Number: 23996-25-0
• EC Number: 245-975-5
• SMILES: CCC1=NC(=CN1CCC#N)C

Properties

• Density: 0.950
• Boiling point: 245-246 °C
• Refractive index: 1.5070
• Flash point: >110 °C

Safety Data

• Hazard Symbols: GHS05;GHS06;GHS07 Danger
• Risk Statements: H301-H302-H315-H318-H319-H335-H412
• Safety Statements: P261-P264-P264+P265-P270-P271-P273-P280-P301+P316-P301+P317-P302+P352-P304+P340-P305+P351+P338-P305+P354+P338-P317-P319-P321-P330-P332+P317-P337+P317-P362+P364-P403+P233-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Skin irritation	Skin Irrit.	2	H315
Eye irritation	Eye Irrit.	2	H319
Acute toxicity	Acute Tox.	4	H302
Serious eye damage	Eye Dam.	1	H318
Chronic hazardous to the aquatic environment	Aquatic Chronic	3	H412
Specific target organ toxicity - single exposure	STOT SE	3	H335
Acute toxicity	Acute Tox.	3	H301
Acute toxicity	Acute Tox.	3	H311
Acute toxicity	Acute Tox.	3	H331
Skin sensitization	Skin Sens.	1	H317
Acute toxicity	Acute Tox.	4	H312

• Transport Information: UN 2810

Discovery and Applications

2-Ethyl-4-methyl-1H-imidazole-1-propanenitrile is an organic compound featuring an imidazole ring substituted with ethyl and methyl groups and a propanenitrile group attached to the nitrogen atom at position 1. This structure imparts both nucleophilic and electrophilic reactivity, making the compound valuable in various synthetic and industrial applications. The compound is used primarily as an intermediate in organic synthesis, particularly in the production of pharmaceuticals, agrochemicals, and specialty chemicals.

The discovery of 2-ethyl-4-methyl-1H-imidazole-1-propanenitrile stems from efforts to modify and functionalize the imidazole ring, a well-known heterocycle in organic chemistry. Imidazole derivatives have been widely studied for their biological activity, as the imidazole core is present in many natural products, including histidine and certain antifungal agents. By introducing alkyl and nitrile substituents, chemists sought to enhance the reactivity and specificity of the imidazole ring, leading to the development of this compound as a versatile synthetic intermediate.

In pharmaceutical synthesis, 2-ethyl-4-methyl-1H-imidazole-1-propanenitrile serves as a key intermediate in the preparation of various drugs. The nitrile group can undergo further transformations, such as hydrolysis to carboxylic acids or reduction to amines, enabling the construction of more complex molecules. This compound is particularly useful in the synthesis of antifungal and antiviral agents, where the imidazole ring plays a crucial role in inhibiting the activity of certain enzymes. The presence of the alkyl substituents increases the lipophilicity of the compound, which can improve drug bioavailability and potency.

In agrochemicals, 2-ethyl-4-methyl-1H-imidazole-1-propanenitrile is employed as a precursor in the synthesis of herbicides and fungicides. The imidazole moiety is known for its ability to interfere with the growth of fungi and weeds by inhibiting key metabolic pathways. By modifying the substituents on the imidazole ring, agrochemical researchers have been able to develop compounds with greater selectivity and lower environmental impact. The nitrile group in this compound provides a reactive site for further derivatization, allowing for the development of targeted crop protection agents.

Additionally, 2-ethyl-4-methyl-1H-imidazole-1-propanenitrile finds application in materials science, particularly in the development of polymers and coatings. The imidazole ring can act as a catalyst in certain polymerization reactions, while the nitrile group can participate in cross-linking, enhancing the mechanical strength and durability of the resulting materials. These properties make the compound valuable in the production of specialty coatings for industrial use, where chemical resistance and durability are critical.

The handling of 2-ethyl-4-methyl-1H-imidazole-1-propanenitrile requires care due to its potential reactivity, particularly with strong acids or bases, which can trigger degradation or unwanted side reactions. As with many nitrile-containing compounds, exposure to high concentrations may pose health risks, so appropriate safety measures, such as personal protective equipment and adequate ventilation, are necessary during its use.

In summary, 2-ethyl-4-methyl-1H-imidazole-1-propanenitrile is a versatile chemical intermediate with significant applications in pharmaceuticals, agrochemicals, and materials science. Its reactivity and structural features make it a valuable tool for chemists seeking to develop novel compounds with enhanced biological or material properties.

References

2010. Improvement of the thermal latency for epoxy-phenolic resins by novel amphiphatic imidazole catalysts. *Macromolecular Research*, 18(4).
DOI: 10.1007/s13233-010-0416-1

2021. Utilization of Steam-Treated and Milling-Treated Lignin from Moso Bamboo as Curing Agent of Epoxy Resin. *Waste and Biomass Valorization*, 12(8).
DOI: 10.1007/s12649-021-01444-8

2020. Lignin as a Coating and Curing Agent on Biodegradable Epoxy Resins. *Reactive and Functional Polymers Volume One*.
DOI: 10.1007/978-3-030-43403-8_9