2-Chloro-4-methylpyrimidine
[CAS# 13036-57-2]

Identification

• Classification: Pharmaceutical intermediate >> Heterocyclic compound intermediate >> Pyridine compound >> Methylpyridine
• Name: 2-Chloro-4-methylpyrimidine
• Molecular Formula: C₅H₅ClN₂
• Molecular Weight: 128.56
• CAS Registry Number: 13036-57-2
• EC Number: 678-759-8
• SMILES: CC1=NC(=NC=C1)Cl

Properties

• Melting point: 35-36 °C
• Flash point: 98 °C

Safety Data

• Hazard Symbols: GHS05;GHS07 Danger
• Risk Statements: H302-H315-H317-H318-H319-H335
• Safety Statements: P261-P264-P264+P265-P270-P271-P272-P280-P301+P317-P302+P352-P304+P340-P305+P351+P338-P305+P354+P338-P317-P319-P321-P330-P332+P317-P333+P317-P337+P317-P362+P364-P403+P233-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Acute toxicity	Acute Tox.	4	H302
Skin irritation	Skin Irrit.	2	H315
Specific target organ toxicity - single exposure	STOT SE	3	H335
Serious eye damage	Eye Dam.	1	H318
Eye irritation	Eye Irrit.	2	H319
Skin sensitization	Skin Sens.	1	H317

Discovery and Applications

2-Chloro-4-methylpyrimidine is a heterocyclic organic compound first synthesized during the mid-20th century as part of ongoing research into pyrimidine derivatives. The compound was identified through targeted chemical synthesis involving the chlorination of 4-methylpyrimidine. Pyrimidines are known for their significance in various biological processes and pharmaceutical applications. The introduction of a chlorine atom to the pyrimidine ring was aimed at enhancing its chemical reactivity and potential as an intermediate in organic synthesis. This discovery enabled the exploration of its properties and applications in pharmaceuticals, agrochemicals, and materials science.

This compound is widely used as a building block in the synthesis of numerous pharmaceutical agents. Its ability to participate in nucleophilic substitution reactions makes it valuable in the construction of complex molecules, including antiviral, anticancer, and antibacterial drugs.

In the development of antiviral medications, 2-chloro-4-methylpyrimidine contributes to the synthesis of compounds targeting viral enzymes or genetic material, helping to inhibit viral replication and treat infections such as hepatitis C and HIV.

It is utilized in the synthesis of anticancer agents that target specific enzymes or receptors involved in cancer cell proliferation. Its incorporation into pharmaceutical compounds can improve efficacy and specificity against cancer cells.

2-Chloro-4-methylpyrimidine is employed in the synthesis of herbicides that selectively target and inhibit key enzymes in plants, leading to effective weed control. Its chemical properties enhance the stability and efficacy of these herbicidal agents, providing solutions for agricultural pest management.

The compound also serves as a precursor in the development of pesticides and fungicides. Its derivatives can disrupt essential biological processes in pests and fungi, protecting crops from damage and enhancing agricultural yields.

In materials science, 2-chloro-4-methylpyrimidine is used to synthesize functional polymers with specific properties. Its reactivity allows it to be incorporated into polymer backbones, resulting in materials with enhanced thermal stability, chemical resistance, and mechanical strength.

The compound can be used to develop advanced materials with unique electronic or optical properties. These materials are applicable in electronics, coatings, and high-performance composites.

As a versatile intermediate, 2-chloro-4-methylpyrimidine facilitates the introduction of various functional groups into target molecules. This property makes it valuable in the synthesis of a wide range of organic compounds, contributing to research in medicinal chemistry, agrochemistry, and material science.

The compound can act as a ligand or catalyst in organic reactions, enabling efficient synthesis of complex molecules. Its use in catalysis improves reaction rates and yields, essential for industrial chemical processes.

2-Chloro-4-methylpyrimidine is used in the production of dyes and pigments for textiles and coatings. Its incorporation into dye molecules can enhance color properties and stability, providing vibrant and durable colors.

References

2008. Synthesis of Unsymmetrical Heterobiaryls Using Palladium-Catalyzed Cross-Coupling Reactions of Lithium Organozincates. Synlett, 2008(18).
DOI: 10.1055/s-0028-1087347