2,3,4,4-tetrachlorocyclobut-2-en-1-one

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Identification

Molecular formula
C4Cl4O
CAS Number
36567-34-3
IUPAC Name
2,3,4,4-tetrachlorocyclobut-2-en-1-one
Molecular Weight
211.85g/mol
Melting Point
compared to similar unsaturated ketones without chlorine atoms.
Boiling Point
(Celsius)
Density
and relatively high melting point compared to similar unsaturated ketones without chlorine atoms.
Synonyms
Tetrachlorocyclobut-2-enone
Interesting facts

Interesting Facts about 2,3,4,4-Tetrachlorocyclobut-2-en-1-one

2,3,4,4-Tetrachlorocyclobut-2-en-1-one is a fascinating organic compound that showcases the complexity of halogenated cyclic structures. Here are some intriguing aspects of this compound:

  • Chlorination Effects: The presence of multiple chlorine atoms significantly influences the reactivity and properties of the compound. Chlorine substituents can modify the electronic characteristics, enhancing its potential for various chemical reactions.
  • Cyclic Structure: As part of the cyclobutene family, this compound possesses interesting ring strain due to its four-membered ring, which can lead to unique behavior in chemical reactions.
  • Applications in Synthesis: The compound’s structure is valuable in organic synthesis, particularly as a building block for more complex molecules. Its halogen functionalities can be exploited in cross-coupling reactions and other synthetic methodologies.
  • Biological Implications: Compounds like 2,3,4,4-tetrachlorocyclobut-2-en-1-one are studied for their biological activities, including antifungal and herbicidal properties, which make them pertinent in agricultural chemistry.
  • Environmental Concerns: The chlorination of organic compounds raises discussions regarding environmental impact and toxicity. Understanding such compounds aids in assessing their safe handling and regulatory measures.

Chemist David M. M. C. van der Wal once noted, "Halogenated organic compounds provide a unique view into the interplay between structure and reactivity." This insight underscores the importance of studying such compounds in the realm of organic chemistry.

Overall, 2,3,4,4-tetrachlorocyclobut-2-en-1-one serves as a prime example of how structural features in organic chemistry can lead to a wide array of applications and considerations in both synthetic and environmental contexts.

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