Methyl 4,6-dichloronicotinate
[CAS# 65973-52-6]

Identification

• Classification: Pharmaceutical intermediate >> Heterocyclic compound intermediate >> Pyridine compound >> Pyridine derivative
• Name: Methyl 4,6-dichloronicotinate
• Molecular Formula: C₇H₅Cl₂NO₂
• Molecular Weight: 206.03
• CAS Registry Number: 65973-52-6
• EC Number: 689-863-8
• SMILES: COC(=O)C1=CN=C(C=C1Cl)Cl

Properties

• Density: 1.4±0.1 g/cm³, Calc.^*
• Melting point: 41-43 ºC (Expl.)
• Index of Refraction: 1.548, Calc.^*
• Boiling Point: 260.0±35.0 ºC (760 mmHg), Calc.^*
• Flash Point: 111.1±25.9 ºC, Calc.^*

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

Safety Data

• Hazard Symbols: GHS07 Warning
• Hazard Statements: H302-H315-H319-H335
• Precautionary Statements: P261-P264-P264+P265-P270-P271-P280-P301+P317-P302+P352-P304+P340-P305+P351+P338-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
Eye irritation	Eye Irrit.	2	H319
Acute toxicity	Acute Tox.	4	H302
Eye irritation	Eye Irrit.	2A	H319

Discovory and Applicatios

Methyl 4,6-dichloronicotinate is an important organic compound derived from the pyridine ring system, characterized by the presence of two chlorine atoms at the 4 and 6 positions on the aromatic ring, along with a methyl ester group at the 1-position. This compound belongs to the class of halogenated nicotinates and is widely used in various fields, including organic synthesis, medicinal chemistry, and material science. Its structure and properties make it a valuable intermediate in the production of other functionalized compounds, as well as a potential bioactive agent.

The synthesis of methyl 4,6-dichloronicotinate typically involves the selective chlorination of methyl nicotinate, followed by purification and crystallization. The chlorination process is often achieved using chlorinating agents such as phosphorus trichloride or chlorine gas under controlled conditions, which allow for the precise incorporation of chlorine atoms at the desired positions. This selective chlorination is essential for the production of methyl 4,6-dichloronicotinate, as it ensures the proper substitution pattern on the pyridine ring, which is critical for its subsequent applications.

One of the primary applications of methyl 4,6-dichloronicotinate is in the field of organic synthesis, where it serves as an important building block for the preparation of other nicotinate derivatives and bioactive molecules. The chlorine atoms in the molecule, being electron-withdrawing groups, significantly influence the reactivity of the compound, making it suitable for nucleophilic substitution reactions. This property allows it to be used as a precursor in the synthesis of more complex compounds with pharmaceutical or agrochemical activity. For example, methyl 4,6-dichloronicotinate can be employed in the preparation of compounds with anti-inflammatory, antimicrobial, and anticancer activities.

In medicinal chemistry, methyl 4,6-dichloronicotinate is being investigated for its potential as a drug candidate. The compound’s structure and functional groups lend themselves to interactions with biological targets, particularly in the treatment of diseases such as cancer and bacterial infections. The methyl ester group enhances the lipophilicity of the molecule, potentially improving its ability to penetrate cell membranes and increasing its bioavailability. The halogenated pyridine ring also plays a role in modulating the compound’s pharmacokinetic properties, including metabolic stability and selective binding to receptors or enzymes.

Another significant application of methyl 4,6-dichloronicotinate is in the field of materials science, where it can be used in the synthesis of functional materials. Its reactivity allows it to be incorporated into polymer systems and metal-organic frameworks (MOFs), which have applications in areas such as gas storage, catalysis, and environmental sensing. Additionally, the compound can be employed in the production of conductive materials, where the chlorine substituents can influence the electronic properties of the final material.

Moreover, the compound’s role in the development of agrochemicals has also been explored. As a derivative of nicotinic acid, which is a precursor to several important plant growth regulators, methyl 4,6-dichloronicotinate may serve as a key intermediate in the synthesis of agrochemicals designed to improve crop yield and resilience. Its chlorination pattern could impart unique activity in plant growth modulation or pest control.

In conclusion, methyl 4,6-dichloronicotinate is a versatile compound with a broad range of applications in organic synthesis, medicinal chemistry, materials science, and agrochemicals. Its discovery and subsequent use in these various fields underline the importance of halogenated nicotinate derivatives in advancing both chemical research and practical applications in several industries.