2-(Chloromethyl)-4-methylquinazoline
[CAS# 109113-72-6]

Identification

• Classification: Pharmaceutical intermediate >> API intermediate
• Name: 2-(Chloromethyl)-4-methylquinazoline
• Molecular Formula: C₁₀H₉ClN₂
• Molecular Weight: 192.64
• CAS Registry Number: 109113-72-6
• EC Number: 640-423-3
• SMILES: CC1=NC(=NC2=CC=CC=C12)CCl

Properties

• Density: 1.251

Safety Data

• Hazard Symbols: GHS05;GHS07;GHS08;GHS09 Danger
• Risk Statements: H302-H317-H318-H341-H400-H410
• Safety Statements: P203-P261-P264-P264+P265-P270-P272-P273-P280-P301+P317-P302+P352-P305+P354+P338-P317-P318-P321-P330-P333+P317-P362+P364-P391-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Serious eye damage	Eye Dam.	1	H318
Chronic hazardous to the aquatic environment	Aquatic Chronic	1	H410
Skin sensitization	Skin Sens.	1	H317
Acute toxicity	Acute Tox.	4	H302
Skin irritation	Skin Irrit.	2	H315
Skin corrosion	Skin Corr.	1C	H314

Discovery and Applications

2-(Chloromethyl)-4-methylquinazoline is an organic compound that has garnered significant interest in medicinal chemistry due to its versatile structure and potential applications in the synthesis of pharmacologically active molecules. This compound, a derivative of quinazoline, features a chloromethyl group at the 2-position and a methyl group at the 4-position on the quinazoline ring. The discovery of 2-(Chloromethyl)-4-methylquinazoline has provided chemists with a valuable building block for the development of a wide range of chemical entities, particularly in the pharmaceutical industry.

The initial discovery of 2-(Chloromethyl)-4-methylquinazoline was driven by the need for new quinazoline derivatives that could serve as intermediates in the synthesis of biologically active compounds. Quinazoline is a heterocyclic aromatic organic compound that has been widely studied for its role in various biological processes. By introducing a chloromethyl group, which is highly reactive, the compound becomes a useful intermediate for further functionalization, allowing for the creation of more complex molecules with potential therapeutic benefits.

In medicinal chemistry, 2-(Chloromethyl)-4-methylquinazoline has been explored as a precursor in the synthesis of kinase inhibitors, a class of drugs that are critical in the treatment of cancers and other diseases involving abnormal cell growth. The quinazoline core is known to interact with ATP-binding sites on kinases, making it a valuable scaffold for designing inhibitors that can selectively target specific enzymes. The chloromethyl group in 2-(Chloromethyl)-4-methylquinazoline enables the introduction of additional functional groups through nucleophilic substitution reactions, further enhancing the potency and selectivity of the resulting kinase inhibitors.

Moreover, 2-(Chloromethyl)-4-methylquinazoline has been used in the synthesis of antifungal and antibacterial agents. The modification of the quinazoline ring with various substituents, facilitated by the chloromethyl group, has led to the development of compounds with enhanced activity against a broad spectrum of microbial pathogens. This has significant implications for the treatment of infectious diseases, especially in the context of rising antibiotic resistance.

In addition to its role in drug development, 2-(Chloromethyl)-4-methylquinazoline is also used in the synthesis of advanced materials. Its reactivity allows it to be incorporated into polymer backbones, creating materials with specific electronic, optical, or mechanical properties. These materials have applications in various fields, including electronics, photonics, and materials science.

The discovery and application of 2-(Chloromethyl)-4-methylquinazoline have thus opened up new avenues in both medicinal chemistry and material science. Its versatility as a synthetic intermediate has made it a valuable tool for researchers seeking to develop new therapeutic agents and advanced materials. As research continues, 2-(Chloromethyl)-4-methylquinazoline is expected to play an increasingly important role in the development of innovative solutions across multiple scientific disciplines.

References

2022. Synthesis and effects of ginkgolides and ginkgolide B derivatives on platelet activating factor induced platelet aggregation in rabbits. Medicinal Chemistry Research.
DOI: 10.1007/s00044-022-02868-0

2004. Of 1,4-Benzodiazepines. Science of Synthesis.
URL: https://science-of-synthesis.thieme.com/app/text/?id=SD-016-00873