5-Chloropyrimidin-2-amine
[CAS# 5428-89-7]

Identification

• Classification: Pharmaceutical intermediate >> Heterocyclic compound intermediate >> Pyrimidine compound >> Chloropyrimidine
• Name: 5-Chloropyrimidin-2-amine
• Synonyms: 2-Amino-5-chloropyridine; 5-Chloro-2-pyrimidinamine
• Molecular Formula: C₄H₄ClN₃
• Molecular Weight: 129.55
• CAS Registry Number: 5428-89-7
• EC Number: 226-581-2
• SMILES: C1=C(C=NC(=N1)N)Cl

Properties

• Density: 1.4±0.1 g/cm³, Calc.^*
• Melting point: 235-238 ºC (Expl.)
• Index of Refraction: 1.618, Calc.^*
• Boiling Point: 314.6±34.0 ºC (760 mmHg), Calc.^*
• Flash Point: 144.1±25.7 ºC, Calc.^*

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

Safety Data

• Hazard Symbols: GHS05;GHS06;GHS07 Danger
• Hazard Statements: H301-H315-H318-H319-H335
• Precautionary Statements: P261-P264-P264+P265-P270-P271-P273-P280-P301+P316-P302+P352-P304+P340-P305+P351+P338-P305+P354+P338-P317-P319-P321-P330-P332+P317-P337+P317-P362+P364-P403+P233-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Serious eye damage	Eye Dam.	1	H318
Acute toxicity	Acute Tox.	3	H301
Specific target organ toxicity - single exposure	STOT SE	3	H335
Skin irritation	Skin Irrit.	2	H315
Acute toxicity	Acute Tox.	4	H302
Eye irritation	Eye Irrit.	2	H319
Eye irritation	Eye Irrit.	2A	H319

• Transport Information: UN 2811

Discovory and Applicatios

5-Chloropyrimidin-2-amine (C4H4ClN3) is a chemical compound that belongs to the class of halogenated pyrimidines. Pyrimidines are heterocyclic compounds that feature a six-membered ring containing nitrogen atoms. The introduction of halogens such as chlorine into the pyrimidine ring structure imparts unique reactivity and properties to the molecule, which makes it a valuable building block in organic synthesis. The discovery of 5-chloropyrimidin-2-amine is part of the broader exploration of halogenated pyrimidines for their diverse applications, particularly in the fields of medicinal chemistry, agrochemicals, and materials science.

The discovery of 5-chloropyrimidin-2-amine can be traced to the early development of halogenated pyrimidines as potential therapeutic agents. Pyrimidines themselves were of significant interest in the early 20th century due to their structural similarity to purines, which are vital components of nucleic acids. The introduction of halogens such as chlorine further increased the interest in these compounds, as halogenation was known to influence the biological activity and reactivity of the molecules. The synthesis of 5-chloropyrimidin-2-amine, through specific halogenation reactions, allowed for the generation of compounds with enhanced bioactivity and selectivity, particularly in enzyme inhibition and receptor binding studies.

One of the main applications of 5-chloropyrimidin-2-amine is in medicinal chemistry, where it serves as a crucial intermediate in the synthesis of various biologically active molecules. The chlorine atom at the 5-position of the pyrimidine ring plays a key role in modulating the compound's pharmacological properties, including its ability to interact with specific enzymes or receptors. This has made 5-chloropyrimidin-2-amine a valuable intermediate in the development of pharmaceuticals, particularly those aimed at treating diseases such as cancer, infections, and neurodegenerative disorders. The compound’s structure allows for the creation of derivatives with enhanced potency, selectivity, and metabolic stability.

In addition to its applications in medicinal chemistry, 5-chloropyrimidin-2-amine is also used in the synthesis of agrochemicals. Pyrimidine derivatives, including 5-chloropyrimidin-2-amine, are known to exhibit herbicidal and pesticidal properties. These compounds can be incorporated into agrochemical formulations to help control the growth of unwanted plants or to protect crops from pests. The chlorine atom in the structure of 5-chloropyrimidin-2-amine enhances its reactivity with biological targets in plants and pests, making it an effective agent for crop protection.

Furthermore, 5-chloropyrimidin-2-amine has applications in the development of materials, especially in the synthesis of polymerizable compounds. Pyrimidine derivatives, when incorporated into polymerization processes, can lead to the formation of materials with unique electronic and optical properties. These materials have potential uses in electronics, light-emitting devices, and sensors. The presence of the chlorine atom in the 5-position of the pyrimidine ring can alter the electronic properties of the material, enhancing its performance in these applications.

Another area where 5-chloropyrimidin-2-amine shows promise is in the field of diagnostics. The compound has been explored for its ability to form complexes with metal ions, which can be utilized in imaging techniques or as sensors for detecting specific biological markers. This ability to interact with metal ions opens up potential uses in medical diagnostics, particularly in detecting and monitoring disease states that involve metal imbalances, such as in cancer or neurological diseases.

In summary, 5-chloropyrimidin-2-amine is a versatile chemical substance with a range of applications across medicinal chemistry, agrochemicals, materials science, and diagnostics. Its discovery as a halogenated pyrimidine derivative has provided a valuable building block for the development of compounds with diverse biological and chemical activities. From its use in drug development to its potential applications in electronics and diagnostics, 5-chloropyrimidin-2-amine continues to be an important compound in both research and industrial settings.