6-Chloroimidazo[1,2-b]pyridazine-3-carbonitrile
[CAS# 123531-54-4]

Identification

• Classification: Organic raw materials >> Heterocyclic compound >> Imidazoles
• Name: 6-Chloroimidazo[1,2-b]pyridazine-3-carbonitrile
• Molecular Formula: C₇H₃ClN₄
• Molecular Weight: 178.58
• CAS Registry Number: 123531-54-4
• SMILES: C1=CC(=NN2C1=NC=C2C#N)Cl

Properties

• Solubility: Very slightly soluble (0.3 g/L) (25 °C), Calc.^*
• Density: 1.56±0.1 g/cm³ (20 °C 760 Torr), Calc.^*
• Index of refraction: 1.743 (Calc.)^*

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

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H315-H319-H335
• Safety Statements: P261-P305+P351+P338

Discovery and Applications

6-Chloroimidazo[1,2-b]pyridazine-3-carbonitrile is a heterocyclic organic compound that contains both imidazole and pyridazine ring systems fused together. It is characterized by the presence of a chloro group at the 6-position of the imidazole ring and a cyano group (-CN) at the 3-position of the pyridazine ring. The structure of this compound consists of a bicyclic system with a nitrogen atom in each ring, contributing to its unique chemical properties.

This compound belongs to a class of heterocyclic compounds that are of interest due to their potential biological activity and usefulness in medicinal chemistry. The presence of both a chloro substituent and a nitrile group makes it a versatile structure for further modifications, enabling its use in the synthesis of novel molecules with enhanced reactivity or biological potency.

Synthesis of 6-chloroimidazo[1,2-b]pyridazine-3-carbonitrile typically involves a multi-step process, beginning with the construction of the imidazo[1,2-b]pyridazine core. This can be achieved through various cyclization reactions, such as those involving condensation of a pyridazine precursor with an imidazole derivative under controlled conditions. The chloro group can be introduced at the 6-position through a halogenation reaction, typically using chlorinating reagents like thionyl chloride (SOCl2) or N-chlorosuccinimide (NCS). The cyano group at the 3-position can be introduced by reacting an appropriate intermediate with a cyanide source, such as potassium cyanide (KCN), to obtain the nitrile derivative.

6-Chloroimidazo[1,2-b]pyridazine-3-carbonitrile has been investigated for its potential as a bioactive compound, particularly in the context of its role in drug development. The imidazole and pyridazine rings are important pharmacophoric elements in medicinal chemistry, as they are commonly found in many biologically active molecules, such as enzyme inhibitors, receptor ligands, and anticancer agents. The chloro and cyano groups on the molecule could influence its binding properties, solubility, and pharmacokinetics, making it a candidate for further biological evaluation.

Research into compounds containing imidazo[1,2-b]pyridazine scaffolds has shown that they can exhibit various biological activities, including antimicrobial, anticancer, and anti-inflammatory effects. The presence of the chloro and nitrile groups could further enhance these activities by modifying the electronic properties of the compound, making it more reactive toward certain biological targets. For example, compounds with similar structures have been found to interact with kinases, enzymes, and other proteins that play critical roles in cell signaling and disease progression.

In addition to its biological activity, 6-chloroimidazo[1,2-b]pyridazine-3-carbonitrile may also have applications in materials science. The fused heterocyclic structure could be useful in the design of novel materials with specific properties, such as semiconducting or electroactive materials. The functional groups on the molecule could also facilitate coordination with metal ions, potentially leading to the development of coordination complexes with unique properties.

In conclusion, 6-chloroimidazo[1,2-b]pyridazine-3-carbonitrile is a heterocyclic compound that exhibits potential in various fields, including medicinal chemistry and materials science. The structure of this molecule, with its chloro and cyano substituents, makes it a versatile intermediate for further chemical modifications and a candidate for the development of bioactive molecules. Ongoing research into its reactivity, biological properties, and applications could lead to the discovery of new drugs or materials with useful characteristics.