2,4,5-Trichloropyrimidine
[CAS# 5750-76-5]

Identification

• Classification: Pharmaceutical intermediate >> Heterocyclic compound intermediate >> Pyrimidine compound >> Chloropyrimidine
• Name: 2,4,5-Trichloropyrimidine
• Synonyms: 2,5,6-Trichloropyrimidine
• Molecular Formula: C₄HCl₃N₂
• Molecular Weight: 183.42
• CAS Registry Number: 5750-76-5
• EC Number: 628-281-0
• SMILES: C1=C(C(=NC(=N1)Cl)Cl)Cl

Properties

• Density: 1.6001
• Refractive index: 1.574
• Boiling point: 84 °C
• Flash point: >110 °C

Safety Data

• Hazard Symbols: GHS05;GHS07 Danger
• Risk Statements: H314-H315-H319-H335
• Safety Statements: P260-P261-P264-P264+P265-P271-P280-P301+P330+P331-P302+P352-P302+P361+P354-P304+P340-P305+P351+P338-P305+P354+P338-P316-P319-P321-P332+P317-P337+P317-P362+P364-P363-P403+P233-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Skin irritation	Skin Irrit.	2	H315
Eye irritation	Eye Irrit.	2	H319
Specific target organ toxicity - single exposure	STOT SE	3	H335
Skin sensitization	Skin Sens.	1	H317
Skin corrosion	Skin Corr.	1B	H314

Discovery and Applications

2,4,5-Trichloropyrimidine was first synthesized and characterized in the early 20th century during investigations into the synthesis of heterocyclic compounds. Chemists were exploring methods to functionalize pyrimidine—a six-membered aromatic ring containing two nitrogen atoms— to create derivatives with diverse properties. Through synthetic routes involving the chlorination of pyrimidine, 2,4,5-Trichloropyrimidine was successfully produced. Its discovery represented a significant advancement in organic chemistry, providing a versatile building block for the synthesis of various organic compounds.

2,4,5-Trichloropyrimidine derivatives serve as key intermediates in the synthesis of herbicides and pesticides. By functionalizing the pyrimidine ring with different substituents, chemists can tailor the properties of these compounds to target specific weeds, insects, and pathogens, contributing to crop protection and yield improvement in agriculture. Some derivatives of 2,4,5-Trichloropyrimidine exhibit fungicidal properties, making them effective in controlling fungal diseases in crops. These compounds disrupt essential biological processes in fungi, leading to their inhibition and preventing crop damage caused by fungal infections.

Researchers explore 2,4,5-Trichloropyrimidine derivatives as potential antiviral agents due to their ability to inhibit viral replication. These compounds target specific viral enzymes or proteins, interfering with viral replication cycles and reducing viral load in infected cells. They hold promise for the development of new antiviral drugs for treating viral infections in humans and animals. Some derivatives of 2,4,5-Trichloropyrimidine exhibit cytotoxic activity against cancer cells, making them potential candidates for anticancer drug development. These compounds interfere with essential cellular processes in cancer cells, such as DNA replication or protein synthesis, leading to cell death and tumor regression. They represent a new avenue for combating various types of cancer with improved efficacy and reduced side effects.

2,4,5-Trichloropyrimidine derivatives are used in polymer synthesis as monomers or crosslinking agents to impart specific properties to polymers. By incorporating these compounds into polymer chains or networks, researchers can enhance mechanical strength, thermal stability, or chemical resistance of the resulting materials, making them suitable for diverse industrial applications, including coatings, adhesives, and composites. Some derivatives of 2,4,5-Trichloropyrimidine exhibit unique properties, such as fluorescence or conductivity, making them valuable in the development of functional materials for electronic devices, sensors, and optoelectronic applications. These compounds serve as building blocks for constructing novel materials with tailored properties for specific technological needs.

References

1972. Pyrimidines. Chemistry of Heterocyclic Compounds, 8(10).
DOI: 10.1007/bf00471851