2-Phenylimidazole
[CAS# 670-96-2]

Identification

• Classification: Organic raw materials >> Heterocyclic compound >> Imidazoles
• Name: 2-Phenylimidazole
• Molecular Formula: C₉H₈N₂
• Molecular Weight: 144.17
• CAS Registry Number: 670-96-2
• EC Number: 211-581-7
• SMILES: C1=CC=C(C=C1)C2=NC=CN2

Properties

• Melting point: 146-148 °C
• Boiling point: 335-337 °C
• Flash point: 200 °C

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H302-H315-H319-H335-H412
• Safety Statements: P261-P264-P270-P271-P273-P280-P301+P312-P302+P352-P304+P340-P305+P351+P338-P312-P330-P332+P313-P337+P313-P362-P403+P233-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Acute toxicity	Acute Tox.	4	H302
Chronic hazardous to the aquatic environment	Aquatic Chronic	3	H412
Eye irritation	Eye Irrit.	2	H319
Skin irritation	Skin Irrit.	2	H315
Specific target organ toxicity - single exposure	STOT SE	3	H335
Eye irritation	Eye Irrit.	2A	H319
Chronic hazardous to the aquatic environment	Aquatic Chronic	2	H411

Discovery and Applications

2-Phenylimidazole is a heterocyclic organic compound, first synthesized in the late 19th century as part of studies exploring imidazole derivatives. Imidazoles are an important class of compounds in organic chemistry, owing to their structural versatility and biological significance. The discovery of 2-Phenylimidazole was driven by the need to develop new imidazole-based compounds for a variety of chemical and medicinal applications. Its core imidazole ring is a common scaffold in many biologically active molecules, and the phenyl group substitution at the 2-position further enhances its chemical reactivity and properties.

One of the major applications of 2-Phenylimidazole is in the field of polymer chemistry, where it is used as a curing agent for epoxy resins. Epoxy resins are widely utilized in adhesives, coatings, and composites due to their high strength and durability. 2-Phenylimidazole acts as an accelerator in the polymerization process, promoting faster and more efficient curing. Its use improves the thermal and mechanical properties of epoxy-based materials, making it valuable in industries ranging from aerospace to electronics, where high-performance materials are required.

In addition to its role in polymer science, 2-Phenylimidazole has found applications in catalysis and organic synthesis. It is often employed as a base or nucleophilic catalyst in various chemical reactions, including the synthesis of heterocyclic compounds and pharmaceuticals. The basicity of 2-Phenylimidazole and its ability to stabilize transition states during reactions make it a versatile catalyst in chemical transformations. This compound has been particularly useful in the synthesis of biologically active molecules, contributing to the development of new drugs and agrochemicals.

2-Phenylimidazole has also been explored for its potential biological activity. Imidazole derivatives are known to exhibit a range of pharmacological effects, including antifungal, antibacterial, and anti-inflammatory properties. While 2-Phenylimidazole itself is not widely used as a pharmaceutical agent, its structure has served as a lead compound in the development of various medicinally relevant imidazole-based drugs. Researchers continue to investigate its potential applications in medicinal chemistry, particularly in designing new compounds with enhanced biological activity.

In materials science, 2-Phenylimidazole is being studied for its role in the development of novel corrosion inhibitors. Imidazoles are known for their ability to form protective films on metal surfaces, preventing oxidation and corrosion. The introduction of a phenyl group in the structure of 2-Phenylimidazole enhances its interaction with metal surfaces, improving its efficacy as a corrosion inhibitor. This application is especially relevant in industries where the protection of metal components from corrosion is critical, such as in oil and gas pipelines and marine environments.

References

2020. 13C CPMAS NMR as a Tool for Full Structural Description of 2-Phenyl Substituted Imidazoles That Overcomes the Effects of Fast Tautomerization. Molecules (Basel, Switzerland), 25(17).
DOI: 10.3390/molecules25173770

2017. Design and synthesis of an indol derivative as antibacterial agent against Staphylococcus aureus. Journal of Chemical Biology, 10(4).
DOI: 10.1007/s12154-017-0173-0

1972. Experimental and theoretical study of the basicity of azoles and their analogs. Chemistry of Heterocyclic Compounds, 8(4).
DOI: 10.1007/bf00477435