4-Methyl-5-imidazolemethanol hydrochloride
[CAS# 38585-62-5]

Identification

• Classification: Organic raw materials >> Heterocyclic compound >> Imidazoles
• Name: 4-Methyl-5-imidazolemethanol hydrochloride
• Synonyms: 4-Hydroxymethyl-5-methylimidazole monohydrochloride; 5-Methyl-4-hydroxymethylimidazole hydrochloride
• Molecular Formula: C₅H₈N₂O.HCl;C₅H₉ClN₂O
• Molecular Weight: 148.59
• CAS Registry Number: 38585-62-5
• EC Number: 254-021-7
• SMILES: CC1=C(N=CN1)CO.Cl

Properties

• Melting point: 231-235 °C (dec.)

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H315-H319-H335
• Safety Statements: P261-P264-P264+P265-P271-P280-P302+P352-P304+P340-P305+P351+P338-P319-P321-P332+P317-P337+P317-P362+P364-P403+P233-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Eye irritation	Eye Irrit.	2	H319
Skin irritation	Skin Irrit.	2	H315
Specific target organ toxicity - single exposure	STOT SE	3	H335

Discovery and Applications

4-Methyl-5-imidazolemethanol hydrochloride is a chemical compound characterized by the imidazole ring system, a five-membered aromatic structure containing nitrogen, along with a hydroxymethyl group and a methyl group attached to the imidazole ring. It is represented by the chemical formula C5H8ClN2O and is often used as an intermediate in organic synthesis, particularly in the pharmaceutical and chemical industries. The compound has drawn attention due to its chemical reactivity, which enables it to be utilized in various synthetic pathways and its potential biological applications.

The discovery of 4-methyl-5-imidazolemethanol hydrochloride is linked to the broader exploration of imidazole derivatives. Imidazole and its derivatives are a well-known class of compounds in medicinal chemistry because of their involvement in several biologically active natural products, such as histamine and certain enzymes. The compound was first synthesized as part of the ongoing research into optimizing the properties of imidazole derivatives for use in pharmaceutical and agricultural applications. The synthesis typically involves the introduction of the hydroxymethyl and methyl groups into the imidazole ring, which is accomplished through methods like nucleophilic substitution reactions or hydroxyalkylation.

4-Methyl-5-imidazolemethanol hydrochloride has a variety of applications, particularly in the development of pharmaceuticals. The imidazole ring is an essential pharmacophore in several well-known drugs, such as antifungals and anti-inflammatory agents. Therefore, derivatives like 4-methyl-5-imidazolemethanol hydrochloride are often utilized as building blocks in the synthesis of more complex molecules with therapeutic potential. Research has shown that this compound can serve as a precursor for the synthesis of imidazole-containing compounds that exhibit antimicrobial, antiviral, and anticancer activities.

One of the key applications of 4-methyl-5-imidazolemethanol hydrochloride is in the development of drugs that target enzymes or receptors that are involved in key physiological processes. Imidazole derivatives are often used to inhibit enzymes like cytochrome P450 or other enzymes involved in drug metabolism, which is crucial in the design of drugs with improved pharmacokinetic properties. Additionally, the compound has been studied for its role in developing molecules that act on G-protein coupled receptors (GPCRs), which are involved in signaling pathways relevant to numerous diseases, including cancer and neurodegenerative disorders.

In addition to its pharmaceutical applications, 4-methyl-5-imidazolemethanol hydrochloride has been explored for use in agricultural chemistry. Compounds containing the imidazole group have demonstrated efficacy in fungicides and plant growth regulators. As an intermediate in the synthesis of agrochemicals, 4-methyl-5-imidazolemethanol hydrochloride can be transformed into more complex molecules with pesticidal activity. The compound's ability to interact with various biological targets makes it an attractive starting material for the development of crop protection agents, contributing to improved agricultural productivity.

The potential for 4-methyl-5-imidazolemethanol hydrochloride extends into materials science as well. Imidazole derivatives have been incorporated into various organic materials for use in sensors, catalysis, and other high-tech applications. The compound's structural flexibility and ability to form coordination complexes with metals enable its use in the creation of advanced materials, including those used in electronics and environmental applications.

In conclusion, 4-methyl-5-imidazolemethanol hydrochloride is a versatile compound with broad applications in pharmaceutical synthesis, agricultural chemistry, and materials science. Its role as a precursor to biologically active molecules makes it an important tool in drug development, while its potential in agricultural chemistry and materials science ensures its continued relevance in both industrial and research settings. Ongoing research into the compound's reactivity and bioactivity will likely reveal further applications and improve its synthetic utility.

References

2003. Cimetidine. Pharmaceutical Substances.
URL: https://pharmaceutical-substances.thieme.com/ps/search-results?docUri=KD-03-0159

2020. Facile bile salt-induced synthesis of porous MnO2 nanoflowers: applications in dye removal and oxidation. SN Applied Sciences, 2(12).
DOI: 10.1007/s42452-020-03731-w