3-Chloropyridine-2-carboxaldehyde
[CAS# 206181-90-0]

Identification

• Classification: Pharmaceutical intermediate >> Heterocyclic compound intermediate >> Pyridine compound >> Chloropyridine
• Name: 3-Chloropyridine-2-carboxaldehyde
• Molecular Formula: C₆H₄ClNO
• Molecular Weight: 141.56
• CAS Registry Number: 206181-90-0
• EC Number: 800-093-5
• SMILES: C1=CC(=C(N=C1)C=O)Cl

Properties

• Density: 1.3±0.1 g/cm³ Calc.^*
• Boiling point: 201.6±20.0 ºC 760 mmHg (Calc.)^*
• Flash point: 75.7±21.8 ºC (Calc.)^*
• Index of refraction: 1.593 (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
Acute toxicity	Acute Tox.	4	H312
Acute toxicity	Acute Tox.	4	H332
Eye irritation	Eye Irrit.	2	H319
Eye irritation	Eye Irrit.	2A	H319

Discovory and Applicatios

3-Chloropyridine-2-carboxaldehyde is a chemical compound that belongs to the class of pyridine derivatives. Pyridine itself is a six-membered heterocyclic aromatic compound containing a nitrogen atom in the ring structure. The introduction of a chloro group at the 3-position of the pyridine ring, coupled with the aldehyde group at the 2-position, gives 3-chloropyridine-2-carboxaldehyde its distinct chemical and physical properties.

This compound is often synthesized through standard synthetic routes, which involve the chlorination of 2-carboxypyridine or related precursors. The aldehyde group, as an electrophilic functional group, is highly reactive, making this compound useful for various chemical reactions, particularly in organic synthesis. The chloro group on the pyridine ring influences the reactivity of the compound, allowing for selective substitution reactions under appropriate conditions.

One of the primary applications of 3-chloropyridine-2-carboxaldehyde is in the pharmaceutical and agrochemical industries. It serves as a key intermediate in the synthesis of various biologically active compounds. For example, it has been employed in the development of certain pharmaceuticals where the pyridine ring and aldehyde functionalities are essential for activity. The compound has also been utilized in the synthesis of various heterocyclic compounds, which are important in the design of novel drugs and therapeutic agents.

In addition to its applications in pharmaceutical synthesis, 3-chloropyridine-2-carboxaldehyde is used in the production of agrochemicals. Its ability to act as a building block for the synthesis of pesticidal compounds makes it valuable in agricultural chemistry. The presence of the chloro group in particular allows for the formation of compounds with specific reactivity that can target biological systems effectively.

The compound also finds uses in the synthesis of ligands and catalysts, particularly in the field of coordination chemistry. The nitrogen atom in the pyridine ring can coordinate with metal ions, and this property is exploited in the development of metal-organic frameworks (MOFs) and other materials that rely on metal-ligand interactions. These materials can be used in catalysis, drug delivery, and other advanced applications in materials science.

In terms of its physical properties, 3-chloropyridine-2-carboxaldehyde is a solid at room temperature and typically appears as a colorless to pale yellow compound. It is soluble in common organic solvents such as ethanol, acetone, and dichloromethane, which makes it amenable to a variety of reaction conditions. The compound’s structure allows for relatively easy manipulation in organic syntheses, where it can undergo a range of reactions including nucleophilic additions, reductions, and further halogenation.

The reactivity of the aldehyde group, in particular, makes 3-chloropyridine-2-carboxaldehyde a versatile intermediate. It can be subjected to condensation reactions with various nucleophiles to form imines, hydrazones, and other derivatives, which are useful in medicinal chemistry. The ability to modify the aldehyde and chloro functionalities selectively provides significant flexibility in the design and synthesis of novel compounds.

In conclusion, 3-chloropyridine-2-carboxaldehyde is a valuable intermediate in organic synthesis with a broad range of applications in the pharmaceutical, agrochemical, and materials science industries. Its unique chemical structure, including the chloro and aldehyde functionalities, allows it to participate in a variety of reactions, making it a key building block for the synthesis of more complex compounds. Its role in the development of new drugs, pesticides, and catalytic materials highlights its importance as a versatile and widely used chemical compound.

References

2006. Unique and Common Metabolites of Thiamethoxam, Clothianidin, and Dinotefuran in Mice. Chemical Research in Toxicology, 19(11).
DOI: 10.1021/tx0601859