4,6-Dichloronicotinonitrile
[CAS# 166526-03-0]

Identification

• Classification: Organic raw materials >> Nitrile compound
• Name: 4,6-Dichloronicotinonitrile
• Synonyms: 4,6-Dichloro-3-pyridinecarbonitrile
• Molecular Formula: C₆H₂Cl₂N₂
• Molecular Weight: 173.00
• CAS Registry Number: 166526-03-0
• EC Number: 893-478-2
• SMILES: C1=C(C(=CN=C1Cl)C#N)Cl

Properties

• Solubility: Very slightly soluble (0.66 g/L) (25 ºC), Calc.^*
• Density: 1.49±0.1 g/cm³ (20 ºC 760 Torr), Calc.^*
• Boiling point: 272.9±35.0 ºC (760 Torr), Calc.^*
• Flash point: 118.8±25.9 ºC, Calc.^*
• Index of refraction: 1.587 (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
Specific target organ toxicity - single exposure	STOT SE	3	H335
Eye irritation	Eye Irrit.	2A	H319
Acute toxicity	Acute Tox.	4	H332
Acute toxicity	Acute Tox.	4	H302
Acute toxicity	Acute Tox.	4	H312
Skin irritation	Skin Irrit.	2	H315

Discovory and Applicatios

4,6-Dichloronicotinonitrile is a chlorinated pyridine derivative that has been documented in the chemical literature primarily as an important intermediate in organic synthesis. The discovery of this compound is linked to efforts in modifying pyridine structures to create new building blocks for pharmaceuticals and agrochemicals. Pyridine and its derivatives have been central in chemical research since the late 19th century, and systematic halogenation of pyridine rings was explored to develop novel compounds with enhanced chemical properties. 4,6-Dichloronicotinonitrile was synthesized as part of these investigations, with the goal of introducing reactive sites at specific positions on the pyridine nucleus to facilitate further functionalization.

The structure of 4,6-Dichloronicotinonitrile features a pyridine ring substituted with chlorine atoms at the 4 and 6 positions and a nitrile group at the 3 position. The presence of electron-withdrawing chlorine and nitrile groups on the aromatic system significantly influences its reactivity, making it a valuable precursor for nucleophilic substitution reactions. This property has been exploited in the synthesis of various heterocyclic compounds, including pharmaceuticals, pesticides, and fine chemicals. Its preparation generally involves chlorination reactions starting from nicotinonitrile derivatives under controlled conditions to achieve substitution at the desired positions without affecting the nitrile group.

One of the main applications of 4,6-Dichloronicotinonitrile is as an intermediate in the production of biologically active molecules. It serves as a key starting material for synthesizing compounds with antimicrobial, antifungal, and herbicidal activities. In medicinal chemistry, the pyridine scaffold is a common motif found in many therapeutic agents, and chlorinated pyridines like 4,6-Dichloronicotinonitrile provide a versatile platform for the development of drug candidates. Researchers utilize this compound to introduce additional functional groups through reactions such as amination, alkylation, and coupling reactions, thereby expanding the chemical diversity of potential drug molecules.

In agricultural chemistry, 4,6-Dichloronicotinonitrile has found use as an intermediate in the synthesis of herbicides and insecticides. The strong electron-withdrawing nature of the substituents enhances the biological activity of derivatives, making them effective in protecting crops against a range of pests and weeds. For instance, derivatives obtained by further substitution or elaboration of 4,6-Dichloronicotinonitrile have been incorporated into formulations aimed at improving crop yield and resistance to environmental stressors.

The utility of 4,6-Dichloronicotinonitrile also extends to material science. Its derivatives have been investigated for the development of advanced materials with specific electronic properties. The presence of halogen atoms and a nitrile group makes it amenable to polymerization reactions and the creation of materials with enhanced conductivity or stability. Although its use in material science is less widespread compared to its pharmaceutical and agrochemical applications, it remains an area of active research.

In the laboratory, 4,6-Dichloronicotinonitrile is valued for its stability and ease of handling compared to other halogenated pyridines. It can be stored under standard conditions without significant degradation and is compatible with a wide range of solvents and reagents used in organic synthesis. The compound's reactivity profile allows for selective modification, making it an attractive intermediate for researchers seeking to design complex molecules efficiently.

In conclusion, 4,6-Dichloronicotinonitrile has a well-documented history as a synthetic intermediate, particularly valued for its role in creating molecules of pharmaceutical and agricultural significance. Its discovery and development are closely tied to broader research efforts aimed at exploiting pyridine chemistry to address practical challenges in medicine, agriculture, and material science.