2-(Chloromethyl)-4,5-dihydro-1H-imidazole hydrochloride
[CAS# 13338-49-3]

Identification

• Classification: Organic raw materials >> Heterocyclic compound >> Imidazoles
• Name: 2-(Chloromethyl)-4,5-dihydro-1H-imidazole hydrochloride
• Molecular Formula: C₄H₇ClN₂^.HCl
• Molecular Weight: 155.03
• CAS Registry Number: 13338-49-3
• EC Number: 641-883-8
• SMILES: C1CN=C(N1)CCl.Cl

Properties

• Melting Point: 195-197 ºC

Safety Data

• Hazard Symbols: GHS07 Warning
• Hazard Statements: H302-H312-H315-H319-H332-H335
• Precautionary Statements: P261-P264-P264+P265-P270-P271-P280-P301+P317-P302+P352-P304+P340-P305+P351+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
Acute toxicity	Acute Tox.	4	H302
Acute toxicity	Acute Tox.	4	H312
Specific target organ toxicity - single exposure	STOT SE	3	H335
Acute toxicity	Acute Tox.	4	H332
Eye irritation	Eye Irrit.	2	H319
Eye irritation	Eye Irrit.	2A	H319

• Transport Information: UN 3261

Discovory and Applicatios

2-(Chloromethyl)-4,5-dihydro-1H-imidazole hydrochloride is a significant chemical compound in the realm of organic synthesis and medicinal chemistry. This compound belongs to the class of imidazole derivatives, which are characterized by a five-membered ring containing two nitrogen atoms. The discovery of this compound is rooted in the ongoing exploration of imidazole derivatives for their biological activities and utility in synthetic chemistry.

The first synthesis of imidazole derivatives can be traced back to the early 20th century, with researchers exploring various substitution patterns to create compounds with diverse biological properties. The chloromethyl group in 2-(Chloromethyl)-4,5-dihydro-1H-imidazole hydrochloride enhances its reactivity, making it a valuable intermediate in the synthesis of more complex organic molecules.

One of the primary applications of 2-(Chloromethyl)-4,5-dihydro-1H-imidazole hydrochloride is in the field of medicinal chemistry, where it serves as a building block for the synthesis of bioactive compounds. The presence of the chloromethyl group allows for further functionalization, enabling the formation of a variety of derivatives with potential pharmacological activities. Compounds derived from this imidazole have been investigated for their antitumor, antifungal, and antimicrobial properties, reflecting the broader interest in imidazole derivatives as promising therapeutic agents.

In addition to its medicinal applications, 2-(Chloromethyl)-4,5-dihydro-1H-imidazole hydrochloride is utilized in the synthesis of polymers and other materials. The compound can be incorporated into polymeric systems to impart desirable properties, such as improved solubility, thermal stability, and biological compatibility. This application is particularly relevant in the development of drug delivery systems, where the controlled release of therapeutic agents is crucial for efficacy and safety.

Moreover, the reactivity of the chloromethyl group makes this compound a useful reagent in organic synthesis. It can participate in nucleophilic substitution reactions, leading to the formation of various functionalized imidazole derivatives. This versatility has made it a valuable tool for chemists aiming to create complex molecules with specific properties for research and industrial applications.

The ongoing research into the properties and applications of 2-(Chloromethyl)-4,5-dihydro-1H-imidazole hydrochloride continues to reveal new possibilities in drug development and materials science. As scientists strive to understand the mechanisms of action and improve the efficacy of imidazole derivatives, the importance of this compound in various fields of chemistry remains evident.

In summary, 2-(Chloromethyl)-4,5-dihydro-1H-imidazole hydrochloride is a noteworthy compound with significant applications in medicinal chemistry, organic synthesis, and materials science. Its discovery and subsequent development highlight the potential of imidazole derivatives in the creation of new therapeutic agents and advanced materials, underscoring the ongoing importance of such compounds in chemical research.

References

2003. Phentolamine. Pharmaceutical Substances.
URL: https://pharmaceutical-substances.thieme.com/ps/search-results?docUri=KD-16-0085

1977. Imidazoles. XII. Synthesis of substituted benzylthioalkylimidazolines. Pharmaceutical Chemistry Journal, 11(4).
DOI: 10.1007/bf01156479