2-Chloro-3-fluoro-4-iodobenzonitrile
[CAS# 1114547-55-5]

Identification

• Classification: Organic raw materials >> Organic fluorine compound >> Fluorobenzonitrile series
• Name: 2-Chloro-3-fluoro-4-iodobenzonitrile
• Molecular Formula: C₇H₂ClFIN
• Molecular Weight: 281.45
• CAS Registry Number: 1114547-55-5
• SMILES: C1=CC(=C(C(=C1C#N)Cl)F)I

Properties

• Density: 2.1±0.1 g/cm³ Calc.^*
• Boiling point: 312.3±42.0 ºC 760 mmHg (Calc.)^*
• Flash point: 142.7±27.9 ºC (Calc.)^*
• Index of refraction: 1.644 (Calc.)^*

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

Safety Data

• Hazard Symbols: GHS07 Warning
• Hazard Statements: H302-H312-H332
• Precautionary Statements: P261-P264-P270-P271-P280-P301+P312-P302+P352-P304+P340-P330-P363-P501

Discovory and Applicatios

2-Chloro-3-fluoro-4-iodobenzonitrile is an organic compound that belongs to the class of halogenated benzonitriles. This compound contains three halogens—chlorine, fluorine, and iodine—on a benzene ring, along with a nitrile group (-CN) at the para position relative to the iodine substituent. The presence of multiple halogens on the aromatic ring contributes to the molecule's unique reactivity and physicochemical properties.

The discovery of halogenated benzonitriles like 2-chloro-3-fluoro-4-iodobenzonitrile is part of ongoing research into compounds with desirable electronic and steric properties. The nitrile group in the molecule is highly polar, which allows it to participate in various interactions with biological macromolecules, particularly enzymes, receptors, and other proteins. This makes halogenated benzonitriles important in the development of biologically active compounds, as they may exhibit a wide range of activities, such as antimicrobial, anticancer, or anti-inflammatory effects.

The halogen atoms in 2-chloro-3-fluoro-4-iodobenzonitrile significantly influence its electronic properties and contribute to its potential applications. The presence of fluorine and chlorine introduces strong electron-withdrawing effects, making the molecule more reactive in certain chemical reactions. Iodine, being a larger atom, has a different electronic character compared to chlorine and fluorine, which can influence the compound's interactions with other molecules. The combination of these three halogens can give the molecule selective reactivity, which is often utilized in designing more potent compounds.

The synthesis of 2-chloro-3-fluoro-4-iodobenzonitrile involves halogenation reactions, where the appropriate halogens are introduced onto the benzene ring. This can be accomplished by using different halogenating agents, such as chlorine, fluorine, and iodine sources, under controlled conditions to ensure the correct positions for each halogen atom. The nitrile group is typically introduced through a nitration or substitution reaction with a nitrile precursor, such as benzoyl chloride or a similar compound.

In terms of applications, 2-chloro-3-fluoro-4-iodobenzonitrile is likely to be of interest in pharmaceutical and agrochemical research. The compound’s halogenated structure is often associated with increased lipophilicity and stability, which are desirable traits in drug design. It could potentially serve as a building block for the development of molecules that exhibit antimicrobial, anticancer, or antiviral activities. The presence of multiple halogens may also make the compound useful in developing highly selective inhibitors of enzymes or receptors involved in diseases such as cancer, inflammation, or microbial infections.

Additionally, halogenated benzonitriles can play a significant role in material science, particularly in the development of electronic materials, polymers, and other advanced materials. The electronic properties of halogen atoms can be tuned for specific applications, making compounds like 2-chloro-3-fluoro-4-iodobenzonitrile important in various industrial applications.

Overall, 2-chloro-3-fluoro-4-iodobenzonitrile is a chemically versatile compound with a combination of halogen substituents that can influence both its reactivity and its potential biological and industrial applications. Its structure makes it an interesting candidate for further exploration in medicinal chemistry, material science, and other fields that require fine-tuned chemical properties.