4-Chloro-6-ethyl-5-fluoropyrimidine
[CAS# 137234-74-3]

Identification

• Classification: Pharmaceutical intermediate >> Heterocyclic compound intermediate >> Pyrimidine compound >> Fluoropyrimidine
• Name: 4-Chloro-6-ethyl-5-fluoropyrimidine
• Molecular Formula: C₆H₆ClFN₂
• Molecular Weight: 160.58
• CAS Registry Number: 137234-74-3
• EC Number: 604-010-1
• SMILES: CCC1=C(C(=NC=N1)Cl)F

Properties

• Density: 1.286
• Boiling point: 211 °C
• Flash point: 81 °C

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H302-H315-H317-H319
• Safety Statements: P261-P264-P264+P265-P270-P272-P280-P301+P317-P302+P352-P305+P351+P338-P321-P330-P332+P317-P333+P317-P337+P317-P362+P364-P501

Hazard Classification

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

Discovery and Applications

4-Chloro-6-ethyl-5-fluoropyrimidine, an organic compound, is part of the pyrimidine family. This compound was first synthesized during the mid-20th century as chemists explored halogenated and alkylated derivatives of pyrimidine. The synthesis of 4-chloro-6-ethyl-5-fluoropyrimidine typically involves the selective halogenation and alkylation of pyrimidine precursors under controlled conditions. Its discovery expanded the toolkit of chemists, enabling the development of new compounds with potential therapeutic applications.

The primary application of 4-chloro-6-ethyl-5-fluoropyrimidine is in pharmaceutical synthesis. Pyrimidine derivatives are well-known for their biological activities, and this compound serves as a key intermediate in the production of various drugs. It is used in the synthesis of antiviral, anticancer, and antibacterial agents. For instance, modifications of this pyrimidine can lead to the development of nucleoside analogs that inhibit viral replication, contributing to treatments for diseases such as HIV and hepatitis. The unique substitution pattern of the chlorine, ethyl, and fluorine groups enhances the compound's ability to interact with biological targets, making it a valuable component in drug design.

In agriculture, 4-chloro-6-ethyl-5-fluoropyrimidine is used as an intermediate in the synthesis of agrochemicals, including herbicides and fungicides. The compound's structure allows for the creation of chemicals that can inhibit the growth of weeds or fungi by interfering with specific biochemical pathways in these organisms.

The compound is also significant in chemical research, particularly in the study of pyrimidine chemistry and the development of new synthetic methodologies. Researchers use 4-chloro-6-ethyl-5-fluoropyrimidine as a starting material to explore various reactions and create novel pyrimidine derivatives.

In material science, fluorinated pyrimidines, including 4-chloro-6-ethyl-5-fluoropyrimidine, are investigated for their properties in the development of advanced materials. These materials can include liquid crystals, organic semiconductors, and components for electronic devices. The presence of fluorine in the molecule imparts unique electronic properties.

The compound is also used in biochemical studies to investigate the role of pyrimidine derivatives in biological systems. It serves as a model compound to study enzyme interactions, metabolic pathways, and the effects of halogenated and alkylated pyrimidines on biological functions.

References

2003. Voriconazole. Pharmaceutical Substances.
URL: https://pharmaceutical-substances.thieme.com/ps/search-results?docUri=KD-22-0034