2-Chloro-5-methoxypyrimidine
[CAS# 22536-65-8]

Identification

• Classification: Pharmaceutical intermediate >> Heterocyclic compound intermediate >> Pyrimidine compound >> Methoxypyrimidine
• Name: 2-Chloro-5-methoxypyrimidine
• Molecular Formula: C₅H₅ClN₂O
• Molecular Weight: 144.56
• CAS Registry Number: 22536-65-8
• EC Number: 636-584-4
• SMILES: COC1=CN=C(N=C1)Cl

Properties

• Density: 1.3±0.1 g/cm³ Calc.^*
• Melting point: 73 - 78 °C (Expl.)
• Boiling point: 268.8±13.0 °C 760 mmHg (Calc.)^*
• Flash point: 116.3±19.8 °C (Calc.)^*
• Index of refraction: 1.52 (Calc.)^*

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

Safety Data

• Hazard Symbols: GHS05;GHS07 Danger
• Risk Statements: H302-H315-H318-H335
• Safety Statements: P261-P264-P264+P265-P270-P271-P280-P301+P317-P302+P352-P304+P340-P305+P354+P338-P317-P319-P321-P330-P332+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
Serious eye damage	Eye Dam.	1	H318
Acute toxicity	Acute Tox.	4	H302
Eye irritation	Eye Irrit.	2	H319

Discovery and Applications

2-Chloro-5-methoxypyrimidine is a chemical compound that belongs to the pyrimidine family, a group of organic compounds containing a six-membered ring with two nitrogen atoms. The structure of 2-chloro-5-methoxypyrimidine consists of a pyrimidine ring with a chlorine atom at the 2-position and a methoxy group (-OCH3) at the 5-position. The presence of these substituents at specific positions on the pyrimidine ring imparts distinct chemical properties to the compound, which are valuable in various applications, particularly in pharmaceutical and chemical industries.

This compound is commonly used as an intermediate in the synthesis of other bioactive molecules and agrochemicals. The introduction of a chlorine atom at the 2-position and a methoxy group at the 5-position influences the electronic characteristics and reactivity of the pyrimidine ring, which can affect its interactions with other chemical entities.

2-Chloro-5-methoxypyrimidine is of interest in medicinal chemistry due to its potential role as a building block for the synthesis of more complex molecules with therapeutic properties. Pyrimidine derivatives are known to play an essential role in nucleic acid metabolism, and their derivatives have been used in the design of drugs targeting various biological processes. The halogen (chlorine) and methoxy (methoxy) substituents can enhance the bioactivity of the compound by modulating its interactions with enzymes, receptors, or other molecular targets.

In addition to its medicinal chemistry applications, 2-chloro-5-methoxypyrimidine can be useful in the preparation of agrochemicals such as herbicides or pesticides. Similar pyrimidine derivatives have shown effectiveness in agricultural applications, acting as growth regulators or pest control agents. The halogenated methoxy-pyrimidine structure can improve the stability and solubility of these compounds, increasing their utility in the agrochemical industry.

While 2-chloro-5-methoxypyrimidine may not be widely known as a commercially available compound, it is recognized in the scientific literature as a useful intermediate for developing more specialized chemical products, including drugs and agricultural chemicals. Its role as a building block in organic synthesis makes it a valuable compound for researchers in various fields, including medicinal chemistry, agricultural chemistry, and material science.

In conclusion, 2-chloro-5-methoxypyrimidine is a versatile compound that serves as a useful intermediate in the synthesis of bioactive molecules and agrochemicals. Its distinct chemical structure, with a chlorine atom and methoxy group at specific positions on the pyrimidine ring, makes it a valuable tool for research and development in medicinal chemistry and chemical industries.

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