2-Chloro-5-methylpyrimidine
[CAS# 22536-61-4]

Identification

• Classification: Pharmaceutical intermediate >> Heterocyclic compound intermediate >> Pyrimidine compound >> Methyl pyrimidine
• Name: 2-Chloro-5-methylpyrimidine
• Molecular Formula: C₅H₅ClN₂
• Molecular Weight: 128.56
• CAS Registry Number: 22536-61-4
• EC Number: 807-915-1
• SMILES: CC1=CN=C(N=C1)Cl

Properties

• Density: 1.2±0.1 g/cm³ Calc.^*
• Melting point: 89 - 92 ºC (Expl.)
• Boiling point: 239.2±9.0 ºC 760 mmHg (Calc.)^*
• Flash point: 121.5±4.3 ºC (Calc.)^*
• Index of refraction: 1.53 (Calc.)^*

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

Safety Data

• Hazard Symbols: GHS07 Warning
• Hazard Statements: H302-H312-H315-H319-H332-H335
• Precautionary 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
Specific target organ toxicity - single exposure	STOT SE	3	H335
Acute toxicity	Acute Tox.	4	H302
Eye irritation	Eye Irrit.	2	H319
Acute toxicity	Acute Tox.	4	H312
Acute toxicity	Acute Tox.	4	H332
Eye irritation	Eye Irrit.	2A	H319

Discovory and Applicatios

2-Chloro-5-methylpyrimidine is a chemical compound belonging to the class of pyrimidine derivatives, which are important in a variety of chemical and biological applications. The structure consists of a six-membered pyrimidine ring, a nitrogen-containing heterocycle, with a chlorine atom attached at the 2-position and a methyl group at the 5-position. This specific substitution pattern provides a unique set of properties that make it relevant in various areas of research and application.

The discovery of 2-chloro-5-methylpyrimidine is part of the broader study of halogenated and methylated pyrimidine derivatives, which are often synthesized for their biological and chemical activities. The presence of the chlorine atom at the 2-position and the methyl group at the 5-position alters the electronic properties of the pyrimidine ring, affecting how the molecule interacts with other substances. These modifications can enhance the compound's stability and influence its solubility, which are crucial factors in its potential use in drug development and materials science.

In medicinal chemistry, halogenated pyrimidine derivatives like 2-chloro-5-methylpyrimidine are of interest due to their potential as building blocks in the synthesis of bioactive compounds. Pyrimidine derivatives are well-known for their role in nucleic acid metabolism, and they are commonly used as intermediates in the synthesis of pharmaceutical agents, particularly in the development of anticancer and antiviral drugs. The halogen substitution, especially chlorine, can increase a compound's ability to interact with specific enzymes or biological targets, potentially making it an effective therapeutic agent.

For example, chloropyrimidines have been studied for their ability to inhibit various enzymes involved in DNA replication or repair, and compounds with similar structures are often used as antimetabolites in cancer treatment. Moreover, the methyl group on the pyrimidine ring can influence the compound's binding affinity to different biological molecules, further enhancing its utility in drug design.

In addition to its medicinal chemistry applications, 2-chloro-5-methylpyrimidine can serve as an intermediate in the synthesis of other more complex organic molecules. It can also be used in the development of agrochemicals, including herbicides or pesticides, due to the effectiveness of certain pyrimidine derivatives in plant growth regulation or pest control.

In conclusion, 2-chloro-5-methylpyrimidine is a versatile compound with significant applications in both medicinal chemistry and the chemical industry. Its structure and functional groups make it a valuable intermediate in the synthesis of various bioactive molecules, offering potential therapeutic and agricultural uses. The chlorinated pyrimidine ring system, in particular, is an important motif in the design of compounds that can interact with a variety of biological targets, making it an area of ongoing interest in chemical research.

References

1993. Chemical properties of ylidene derivatives of azines. 7. Conversions of 5-methyl(phenyl)-substituted 1,2-dihydro-2-pyrimidinylidenemalononitriles by nitric acid. Chemistry of Heterocyclic Compounds, 29(4).
DOI: 10.1007/bf00529882

2004. Palladium-Catalyzed Cross Coupling with Organostannanes (Stille Reaction). Science of Synthesis, 1.
URL: https://science-of-synthesis.thieme.com/app/text/?id=SD-010-00338

2011. C-Alkylations. Science of Synthesis, 1.
URL: https://science-of-synthesis.thieme.com/app/text/?id=SD-047-00517