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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
State
State

At room temperature, 2,3,4,4-tetrachlorocyclobut-2-en-1-one is typically found in a solid state. The presence of four chlorine atoms contributes to its increased density and relatively high melting point compared to similar unsaturated ketones without chlorine atoms.

Melting point (Celsius)
63.00
Melting point (Kelvin)
336.00
Boiling point (Celsius)
221.00
Boiling point (Kelvin)
494.00
General information
Molecular weight
211.85g/mol
Molar mass
211.8490g/mol
Density
1.6700g/cm3
Appearence

2,3,4,4-Tetrachlorocyclobut-2-en-1-one typically appears as a pale yellow crystalline solid. It is known for its distinct cyclic chlorination on the butenone structure, giving it unique properties compared to similar compounds. In pure form, this compound may appear either as a powder or as granular crystals.

Comment on solubility

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

The solubility of 2,3,4,4-tetrachlorocyclobut-2-en-1-one is a key factor that influences its behavior in various environments. Understanding its solubility characteristics involves considering several important aspects:

  • Solvents: This compound is known to have limited solubility in water, due to its chlorinated structure, which typically leads to hydrophobic interactions. However, it is more soluble in organic solvents such as ethanol, acetone, and dichloromethane.
  • Temperature Effects: As with many organic compounds, increased temperature generally enhances solubility. Therefore, solubility may increase when the solvent is heated.
  • Structural Impact: The presence of multiple chlorine atoms in its molecular structure contributes to its unique solubility behavior. Chlorinated compounds often exhibit distinct polarity and intermolecular forces that affect how they interact with different solvents.

As a rule of thumb, when working with 2,3,4,4-tetrachlorocyclobut-2-en-1-one, it is essential to consider these factors to predict its solubility in both laboratory and industrial applications. Remember, knowing the solubility characteristics of a compound not only dictates its potential uses but also governs safety protocols and disposal methods.

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.

Synonyms
Tetrachlorocyclobut-2-enone
2,3,4,4-Tetrachloro-2-cyclobuten-1-one
221-704-6
Perchlorocyclobutenone
3200-96-2
Tetrachlorocyclobutenone
Perchlorocyclobut-2-enone
2,3,4,4-tetrachlorocyclobut-2-en-1-one
Perchloro-2-cyclobuten-1-one
Perchloro-2-cyclobutene-1-one
2-CYCLOBUTEN-1-ONE, 2,3,4,4-TETRACHLORO-
Tetrachloro-2-cyclobutene-1-one
2,3,4,4-tetrachloro-cyclobut-2-en-1-one
EINECS 221-704-6
NSC 125696
BRN 1864941
TCCBO
perchloro-2-cyclobutenone
SCHEMBL7620046
DTXSID30185834
WLN: L4V BHJ BG BG CG DG
NSC125696
AKOS024333070
NSC-125696
2-Cyclobuten-1-one,3,4,4-tetrachloro-
DB-222197
NS00029205
2,3,4,4-Tetrachloro-2-cyclobuten-1-one #
InChI=1/C4Cl4O/c5-1-2(6)4(7,8)3(1)