1-Chloro-1-fluoroethylene
[CAS# 2317-91-1]

Identification

• Classification: Chemical reagent >> Organic reagent >> Olefins (cyclic and non-cyclic)
• Name: 1-Chloro-1-fluoroethylene
• Synonyms: fluorochloroethylene
• Molecular Formula: C₂H₂ClF
• Molecular Weight: 80.49
• CAS Registry Number: 2317-91-1
• EC Number: 219-027-6
• SMILES: C=C(F)Cl

Properties

• Density: 1.5±0.1 g/cm³, Calc.^*
• Melting point: -169 °C (Expl.)
• Index of Refraction: 1.534, Calc.^*
• Boiling Point: 315.9±42.0 °C (760 mmHg), Calc.^*, -24 °C (Expl.)
• Flash Point: 144.9±27.9 °C, Calc.^*

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

Safety Data

• Hazard Symbols: GHS02;GHS04 Warning
• Risk Statements: H221-H280-H315-H319-H335
• Safety Statements: P210-P260-P280

Discovery and Applications

1-Chloro-1-fluoroethylene (C₂H₂ClF) is a halogenated olefin that contains both chlorine and fluorine substituents on an ethylene backbone. This compound belongs to the class of fluoroalkenes, which have been investigated for their chemical properties and industrial applications. The presence of both halogens in its structure influences its reactivity and stability, making it a useful intermediate in the synthesis of fluorinated organic compounds.

The synthesis of 1-chloro-1-fluoroethylene has been achieved through halogen exchange reactions, involving the fluorination of chlorinated precursors or the selective chlorination of fluoroalkenes. Fluorination reactions often require specialized fluorinating agents such as hydrogen fluoride or metal fluorides, while chlorination can be conducted using conventional chlorinating reagents under controlled conditions. The production of this compound requires careful handling due to the reactivity of halogenated olefins and the potential formation of byproducts.

1-Chloro-1-fluoroethylene has been studied in organic synthesis, particularly as a reactive intermediate in the development of fluorinated materials. The presence of both chlorine and fluorine allows for selective transformations in synthetic chemistry, including nucleophilic substitutions and addition reactions. This makes it valuable in the production of specialty chemicals where fluorine incorporation enhances thermal stability, chemical resistance, or biological activity.

In the field of polymer chemistry, fluoroalkenes serve as precursors for the synthesis of fluorinated polymers and copolymers with applications in coatings, elastomers, and specialty plastics. While 1-chloro-1-fluoroethylene itself is not widely used as a monomer, its structural features contribute to the development of related fluorinated building blocks that improve the performance of polymeric materials. The controlled introduction of fluorine in polymeric structures can lead to materials with low surface energy, hydrophobic properties, and enhanced durability.

Due to the presence of halogens, 1-chloro-1-fluoroethylene exhibits characteristic reactivity that must be carefully managed in industrial processes. The handling and storage of this compound require appropriate safety precautions, including the use of sealed containers, controlled temperature conditions, and protective equipment to prevent exposure. Halogenated olefins can undergo decomposition or polymerization under certain conditions, necessitating proper containment and hazard assessment.

Research into halogenated ethylenes continues to explore their potential applications in chemical synthesis and material science. The study of 1-chloro-1-fluoroethylene and related compounds contributes to advancements in fluorine chemistry, providing new opportunities for the design of functionalized organic molecules and advanced materials.

References

2011. Rotational spectroscopy and molecular structure of the 1-chloro-1-fluoroethylene-acetylene complex. The Journal of Chemical Physics, 134(3).
DOI: 10.1063/1.3517494