Oxalyl fluoride

Oxalyl fluoride is a chemical compound with the formula (COF)₂. It is a colorless gas that condenses to a pale-yellow liquid. It is part of the carbonyl halide family, which includes compounds like phosgene. Oxalyl fluoride is used primarily in organic synthesis and materials science for the introduction of fluorine into organic molecules.

Properties

Oxalyl fluoride is characterized by its reactivity with water, forming carbon dioxide, hydrogen fluoride, and carbon monoxide. This reaction makes it hazardous to handle without proper safety precautions. It is also reactive towards alcohols and amines, making it useful in organic synthesis for the introduction of fluorine or for the activation of carbonyl groups.

Synthesis

Oxalyl fluoride can be synthesized by the reaction of oxalic acid with hydrogen fluoride in the presence of a catalyst, typically a Lewis acid like boron trifluoride (BF₃). Another method involves the reaction of carbon monoxide with fluorine gas, although this method is less commonly used due to the highly reactive nature of elemental fluorine.

Applications

In organic synthesis, oxalyl fluoride is used as a reagent for the fluorination of organic compounds. It is particularly useful for the introduction of fluorine atoms into aromatic compounds, a process that can significantly alter the physical and chemical properties of the target molecules, such as their electronic structure, reactivity, and solubility. Additionally, oxalyl fluoride is used in the synthesis of fluoropolymers and in the preparation of other fluorinated organic compounds.

Safety

Oxalyl fluoride is a potent irritant to the skin, eyes, and respiratory system. It can decompose to release toxic gases such as carbon monoxide and hydrogen fluoride upon contact with water or moisture. Proper handling includes the use of personal protective equipment (PPE), such as gloves and goggles, and working in a well-ventilated area or under a fume hood. In case of exposure, immediate measures should be taken to remove the person from the exposure site and seek medical attention.