2-Chloro-4-cyanopyridine
[CAS# 33252-30-1]

Identification

• Classification: Pharmaceutical intermediate >> Heterocyclic compound intermediate >> Pyridine compound >> Cyanopyridine
• Name: 2-Chloro-4-cyanopyridine
• Synonyms: 4-Cyano-2-chloropyridine
• Molecular Formula: C₆H₃ClN₂
• Molecular Weight: 138.55
• CAS Registry Number: 33252-30-1
• EC Number: 608-852-0
• SMILES: C1=CN=C(C=C1C#N)Cl

Properties

• Density: 1.3±0.1 g/cm³, Calc.^*
• Melting point: 69-73 °C (Expl.)
• Index of Refraction: 1.566, Calc.^*
• Boiling Point: 218.9±20.0 °C (760 mmHg), Calc.^*, 243-245.7 °C (Expl.)
• Flash Point: 86.2±21.8 °C, Calc.^*

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

Safety Data

• Hazard Symbols: GHS06;GHS07 Danger
• Risk Statements: H302-H311-H315-H319-H332-H335
• Safety Statements: P261-P262-P264-P264+P265-P270-P271-P280-P301+P317-P302+P352-P304+P340-P305+P351+P338-P316-P317-P319-P321-P330-P332+P317-P337+P317-P361+P364-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
Eye irritation	Eye Irrit.	2	H319
Acute toxicity	Acute Tox.	4	H332
Acute toxicity	Acute Tox.	4	H302
Acute toxicity	Acute Tox.	3	H311
Acute toxicity	Acute Tox.	4	H312
Eye irritation	Eye Irrit.	2A	H319
Germ cell mutagenicity	Muta.	2	H341
Respiratory sensitization	Resp. Sens.	1	H334
Acute toxicity	Acute Tox.	3	H301
Acute toxicity	Acute Tox.	3	H331
Skin sensitization	Skin Sens.	1	H317

Discovery and Applications

2-Chloro-4-cyanopyridine is a chemical compound that belongs to the class of halogenated pyridine derivatives. Its molecular formula is C6H3ClN2, and it consists of a pyridine ring with a chlorine atom at the 2-position and a cyano group at the 4-position. The compound is typically synthesized through various methods, including the halogenation of 4-cyanopyridine and other organic synthetic routes that involve the introduction of the chlorine atom at the desired position.

The discovery of 2-chloro-4-cyanopyridine is closely tied to the ongoing research in the field of heterocyclic chemistry, where pyridine derivatives have been studied for their wide range of biological and chemical properties. Pyridine and its derivatives are of significant interest in drug discovery, agrochemicals, and materials science due to their ability to interact with biological systems and their stability in various chemical reactions.

2-Chloro-4-cyanopyridine has found applications in several areas of chemical research and industrial processes. One of the most notable uses is in the synthesis of pharmaceutical intermediates. The presence of both a chlorine atom and a cyano group on the pyridine ring makes 2-chloro-4-cyanopyridine a versatile building block in the preparation of more complex organic compounds. It can be used in the design and synthesis of bioactive molecules, including potential drug candidates.

The compound has also been investigated in the context of agrochemical research, particularly for its potential use as an intermediate in the synthesis of herbicides and pesticides. Pyridine derivatives, including 2-chloro-4-cyanopyridine, have been found to exhibit various biological activities, including antifungal, antibacterial, and herbicidal properties. The ability of 2-chloro-4-cyanopyridine to serve as a precursor to such compounds makes it a valuable chemical in agricultural applications.

In addition to its use in pharmaceuticals and agrochemicals, 2-chloro-4-cyanopyridine has been explored for its role in material science. Pyridine derivatives are known for their ability to coordinate with metal ions, and 2-chloro-4-cyanopyridine is no exception. Its ability to form metal complexes has been studied in the development of catalytic systems and materials with specialized properties.

While the primary applications of 2-chloro-4-cyanopyridine are in the fields of organic synthesis, drug development, and agrochemicals, it is also utilized in research laboratories as a reagent in various synthetic transformations. Its chemical reactivity, due to the presence of the chlorine and cyano groups, makes it useful for modifying or constructing other organic molecules.

Overall, 2-chloro-4-cyanopyridine is a useful compound in the synthesis of pharmaceutical intermediates, agrochemicals, and materials with potential applications in catalysis. Its relatively simple structure, combined with its ability to undergo various chemical reactions, makes it an important building block in organic chemistry.

References

2019. Synthesis of azachromones and azachromanones. Chemistry of Heterocyclic Compounds, 55(11).
DOI: 10.1007/s10593-019-02570-x

2019. Synthesis and properties of 2,3-heteroannulated thiochromones - hetero analogs of thioxanthone. Chemistry of Heterocyclic Compounds, 55(2).
DOI: 10.1007/s10593-019-02426-4