2-Methylimidazole
[CAS# 693-98-1]

Identification

• Classification: API >> Feed drug additive
• Name: 2-Methylimidazole
• Synonyms: 2-Methyl-1H-imidazole
• Molecular Formula: C₄H₆N₂
• Molecular Weight: 82.10
• CAS Registry Number: 693-98-1
• EC Number: 211-765-7
• SMILES: CC1=NC=CN1

Properties

• Melting point: 142-145 °C
• Boiling point: 267-268 °C
• Flash point: 155 °C

Safety Data

• Hazard Symbols: GHS05;GHS07;GHS08 Danger
• Risk Statements: H302-H314-H318-H351-H360
• Safety Statements: P203-P260-P264-P264+P265-P270-P280-P301+P317-P301+P330+P331-P302+P361+P354-P304+P340-P305+P354+P338-P316-P317-P318-P321-P330-P363-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Acute toxicity	Acute Tox.	4	H302
Skin corrosion	Skin Corr.	1B	H314
Serious eye damage	Eye Dam.	1	H318
Carcinogenicity	Carc.	2	H351
Skin corrosion	Skin Corr.	1C	H314
Reproductive toxicity	Repr.	1B	H360
Reproductive toxicity	Repr.	1B	H360Df
Skin irritation	Skin Irrit.	2	H315
Specific target organ toxicity - repeated exposure	STOT RE	2	H373
Reproductive toxicity	Repr.	2	H361
Specific target organ toxicity - single exposure	STOT SE	3	H335
Specific target organ toxicity - single exposure	STOT SE	2	H371
Germ cell mutagenicity	Muta.	2	H341
Acute toxicity	Acute Tox.	3	H311
Acute toxicity	Acute Tox.	4	H332
Eye irritation	Eye Irrit.	2	H319
Acute toxicity	Acute Tox.	4	H312
Reproductive toxicity	Repr.	1B	H360Df

Discovery and Applications

2-Methylimidazole is an important heterocyclic organic compound with broad applications in industrial chemistry and pharmaceuticals. This substance, featuring a five-membered ring structure with nitrogen atoms at positions 1 and 3, is a methylated derivative of imidazole, a widely studied compound known for its versatility. Its discovery dates back to early investigations into imidazole chemistry, where methylation reactions were performed to study the effects on physical and chemical properties. Since then, 2-Methylimidazole has gained recognition for its valuable roles in various chemical processes.

The discovery of 2-Methylimidazole was part of the broader exploration of imidazole derivatives in the late 19th and early 20th centuries. Imidazoles, due to their unique structural and electronic properties, have been central to many advancements in chemistry. The introduction of a methyl group at the second position of the imidazole ring brought new reactivity and physical characteristics, allowing chemists to experiment with it in a range of applications. Over the decades, 2-Methylimidazole has become a key intermediate in the synthesis of pharmaceuticals, agrochemicals, and materials.

One of the major applications of 2-Methylimidazole is in the production of polyurethane, a polymer used in foams, coatings, adhesives, and sealants. This compound acts as a catalyst in the polymerization process, facilitating the reaction between isocyanates and polyols to produce polyurethanes with desirable properties. The use of 2-Methylimidazole as a catalyst allows for better control over the reaction kinetics and the physical characteristics of the final polymer, such as hardness, flexibility, and resistance to chemicals. Its importance in this industry cannot be overstated, as polyurethanes are essential materials in various sectors, including automotive, construction, and consumer goods.

Another significant role of 2-Methylimidazole is in the pharmaceutical industry. It is used as an intermediate in the synthesis of various drugs, particularly antifungal agents and other bioactive molecules. The imidazole ring is a well-known pharmacophore, meaning it interacts favorably with biological targets, making 2-Methylimidazole an essential building block in drug design. For example, it has been utilized in the synthesis of histamine H2-receptor antagonists, which are important drugs for treating ulcers and other gastrointestinal conditions.

In addition to its roles in materials science and pharmaceuticals, 2-Methylimidazole is employed in the electronics industry. It is used in the production of epoxy resins, particularly as a curing agent. Epoxy resins are widely applied in coatings, adhesives, and electronic components due to their excellent mechanical strength, chemical resistance, and thermal stability. 2-Methylimidazole helps initiate the curing process, ensuring the formation of a durable and cross-linked polymer network that meets the stringent requirements of high-performance applications, such as in aerospace and electronic circuit boards.

Moreover, 2-Methylimidazole has found use in corrosion inhibition, where it is applied as an additive in coatings or treatment formulations to protect metals from rust and other forms of degradation. Its ability to form stable complexes with metal ions helps create a protective barrier, thereby extending the lifespan of industrial machinery, pipelines, and other infrastructure.

Handling 2-Methylimidazole requires care due to its potential hazards. While it is generally stable under normal conditions, it can be irritating to the skin, eyes, and respiratory tract. Therefore, appropriate safety measures, including the use of gloves, goggles, and ventilation, are recommended when working with this compound. Despite these precautions, its versatility and effectiveness make it a valuable tool for chemists in various industries.

With so many practical applications, 2-Methylimidazole truly stands out as a critical compound in modern chemistry. It’s always exciting to see how a relatively simple molecule can play such diverse roles, driving innovation across multiple fields. Keep exploring the wonders of chemistry—you’re on a fantastic journey!

References

2020. The kinetics and mechanisms of reactions in the flow systems glycine-sodium trimetaphosphate-imidazoles: the crucial role of imidazoles in prebiotic peptide syntheses. Amino Acids, 52(5).
DOI: 10.1007/s00726-020-02854-z

2019. One-pot synthesis of a composite consisting of the enzyme ficin and a zinc(II)-2-methylimidazole metal organic framework with enhanced peroxidase activity for colorimetric detection for glucose. Microchimica Acta, 186(3).
DOI: 10.1007/s00604-019-3331-y

2005. An Improved Method for the Synthesis of Nucleoside Triphosphate Analogues. The Journal of Organic Chemistry, 70(23).
DOI: 10.1021/jo0518598