Ethyl 2-chloropyrimidine-5-carboxylate
[CAS# 89793-12-4]

Identification

• Classification: Pharmaceutical intermediate >> Heterocyclic compound intermediate >> Pyrimidine compound >> Chloropyrimidine
• Name: Ethyl 2-chloropyrimidine-5-carboxylate
• Molecular Formula: C₇H₇ClN₂O₂
• Molecular Weight: 186.59
• CAS Registry Number: 89793-12-4
• EC Number: 689-821-9
• SMILES: CCOC(=O)C1=CN=C(N=C1)Cl

Properties

• Density: 1.3±0.1 g/cm³ Calc.^*
• Melting point: 52 - 60 °C (Expl.)
• Boiling point: 314.2±15.0 °C 760 mmHg (Calc.)^*, 80 °C (Expl.)
• Flash point: 143.8±20.4 °C (Calc.)^*
• Index of refraction: 1.527 (Calc.)^*

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software.

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H302-H302-H312-H315-H319-H332-H335
• Safety Statements: P261-P264-P264+P265-P270-P271-P280-P301+P317-P302+P352-P304+P340-P305+P351+P338-P317-P319-P321-P330-P332+P317-P337+P317-P362+P364-P403+P233-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Skin irritation	Skin Irrit.	2	H315
Eye irritation	Eye Irrit.	2	H319
Acute toxicity	Acute Tox.	4	H302
Specific target organ toxicity - single exposure	STOT SE	3	H335
Acute toxicity	Acute Tox.	4	H312
Acute toxicity	Acute Tox.	4	H332
Eye irritation	Eye Irrit.	2A	H319

Discovery and Applications

Ethyl 2-chloropyrimidine-5-carboxylate is an organic compound belonging to the class of substituted pyrimidine derivatives. It consists of a pyrimidine ring, which is a six-membered heterocyclic ring containing nitrogen atoms at positions 1 and 3. The compound features an ethyl ester group attached to the carboxyl group at position 5 and a chlorine atom at position 2 on the pyrimidine ring. The molecular formula for ethyl 2-chloropyrimidine-5-carboxylate is C7H7ClN2O2.

This compound is primarily synthesized through electrophilic substitution reactions, where the chlorination of pyrimidine derivatives occurs at specific positions, followed by esterification to form the ethyl ester. The precise substitution pattern achieved during the synthesis is crucial for tailoring the chemical reactivity of the compound, making it useful as an intermediate for further chemical transformations.

Ethyl 2-chloropyrimidine-5-carboxylate has a variety of applications, especially in the field of organic synthesis. Its structure makes it an attractive building block for the synthesis of more complex molecules, particularly those with biological or pharmacological significance. The presence of the chlorine atom at position 2 enhances the electrophilic character of the pyrimidine ring, facilitating further reactions such as nucleophilic substitution and condensation reactions. This property is useful for developing derivatives with modified pharmacological properties, including those targeting specific biological pathways.

In medicinal chemistry, ethyl 2-chloropyrimidine-5-carboxylate has been investigated as a precursor to biologically active compounds. The pyrimidine ring system is a common structural motif in many pharmaceuticals, as it can interact with various biological targets, such as enzymes, receptors, and DNA. Substituted pyrimidines are often explored for their potential antimicrobial, anticancer, and antiviral activities. Researchers may use ethyl 2-chloropyrimidine-5-carboxylate as a starting point for synthesizing more complex molecules with these desired biological effects.

In addition to medicinal chemistry, the compound has applications in the field of agrochemicals. Pyrimidine derivatives, including ethyl 2-chloropyrimidine-5-carboxylate, are valuable intermediates in the synthesis of herbicides, fungicides, and pesticides. The introduction of the chlorine atom can enhance the stability and reactivity of the molecule, allowing it to interact with biological systems in a way that can effectively control pests and diseases in crops. By modifying the structure of the compound, chemists can design new agrochemical agents with improved efficacy and selectivity.

Ethyl 2-chloropyrimidine-5-carboxylate is also useful in the synthesis of materials and polymers. The chemical reactivity of the pyrimidine ring and the ester group makes it an excellent candidate for incorporating into functional materials, such as coatings, dyes, and electronic materials. The ability to easily modify the structure of the compound allows researchers to create materials with tailored properties, such as enhanced stability, conductivity, or optical characteristics.

The compound’s synthetic versatility makes it a valuable intermediate for the preparation of a wide range of other organic compounds. In particular, the chloropyrimidine structure offers multiple avenues for further substitution or functionalization, which can lead to the development of compounds with diverse chemical, physical, and biological properties. By altering the functional groups attached to the pyrimidine ring, researchers can design molecules for specific applications, from pharmaceuticals to industrial materials.

In conclusion, ethyl 2-chloropyrimidine-5-carboxylate is a versatile compound with significant applications in organic synthesis, medicinal chemistry, agrochemicals, and materials science. Its ability to undergo further chemical modifications makes it an important building block for the development of more complex molecules with diverse properties. Research into the compound’s potential continues to expand its utility in various industries, including drug development, pest control, and material fabrication. Its role as an intermediate in chemical synthesis ensures that it will remain an important substance in the production of a wide range of functional molecules.

References

2024. Synthetic account on indoles and their analogues as potential anti-plasmodial agents. Molecular Diversity, 28(3).
DOI: 10.1007/s11030-024-10842-8