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1,1,2,3,4-Pentachlorobutadiene

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Identification
Molecular formula
C4H4Cl2
CAS number
3414-55-9
IUPAC name
1,1-dichlorobuta-1,3-diene;1,2-dichlorobuta-1,3-diene;1,4-dichlorobuta-1,3-diene
State
State

At room temperature, 1,1-dichlorobuta-1,3-diene exists as a volatile liquid with a tendency to vaporize, especially when it is agitated or warmed.

Melting point (Celsius)
-71.00
Melting point (Kelvin)
202.00
Boiling point (Celsius)
141.80
Boiling point (Kelvin)
414.95
General information
Molecular weight
108.97g/mol
Molar mass
108.9740g/mol
Density
1.2860g/cm3
Appearence

1,1-Dichlorobuta-1,3-diene is a colorless liquid that tends to form fumes upon exposure to air. It may appear slightly yellowish when impure or when stored for extended periods. It is often stored under inert gases to prevent degradation.

Comment on solubility

Solubility of Dichlorobuta-1,3-dienes

The solubility of the dichlorobuta-1,3-diene compounds, specifically 1,1-dichlorobuta-1,3-diene, 1,2-dichlorobuta-1,3-diene, and 1,4-dichlorobuta-1,3-diene, is an intriguing subject due to their unique structural variations. Each component of this family displays differing solubility characteristics that can be largely attributed to the position of the chlorine substituents. Here’s a closer look:

  • 1,1-Dichlorobuta-1,3-diene: Generally, this compound exhibits a tendency to be soluble in organic solvents like ether and acetone. The presence of two chlorine atoms on the same carbon enhances polarity, which facilitates dissolving in polar solvents.
  • 1,2-Dichlorobuta-1,3-diene: This isomer typically shows intermediate solubility characteristics. It is moderately soluble in both polar and non-polar solvents, owing to the balanced spatial arrangement of its functionalities.
  • 1,4-Dichlorobuta-1,3-diene: This compound tends to be less soluble in polar solvents as the distance between the chlorine atoms reduces their collective polar contribution, making it more compatible with non-polar environments.

In summary, when considering the solubility of dichlorobuta-1,3-dienes, take note of the following key points:

  1. Structure dictates solubility behavior; specific positioning of substituents plays a crucial role.
  2. Polarity and solvent interactions determine how well each compound dissolves.
  3. Testing in various solvent environments provides practical insights into their solubility profiles.

In conclusion, understanding the solubility of these compounds not only enhances their practical applications but also underscores the importance of molecular structure in determining chemical behavior.

Interesting facts

1,1-Dichlorobuta-1,3-diene

1,1-Dichlorobuta-1,3-diene, commonly noted for its unique structure, has two chlorine atoms attached to the first carbon of the butadiene backbone. Its significance in the field of organic chemistry is highlighted by the following points:

  • Versatility in Synthesis: This compound is often utilized in organic synthesis as a building block for more complex molecules, allowing chemists to explore various synthetic pathways.
  • Reactivity: The presence of double bonds and halogen substitutions makes it a reactive compound, engaging in addition reactions with nucleophiles and electrophiles.
  • Research Applications: Due to its unique properties, it serves as a subject of study to understand reaction mechanisms and the effects of substitution on chemical reactivity.

As chemists delve deeper into the world of 1,1-dichlorobuta-1,3-diene, they often find themselves enchanted by its transformative potential in synthesizing novel compounds.

1,2-Dichlorobuta-1,3-diene

This compound exhibits a fascinating arrangement of chlorine atoms relative to the butadiene framework, specifically at the second and first positions of the chain. Here are some intriguing aspects:

  • Chirality Potential: The configuration of the chlorines can create chiral centers, making 1,2-dichlorobuta-1,3-diene an interesting candidate in studies of stereochemistry.
  • Environmental Implications: As a derivative of butadiene, it relates to discussions on environmental chemistry, particularly in terms of pollutants and their transformations.
  • Polymer Chemistry: Its derivatives are often considered in the design of polymers, broadening the scope of materials science and industrial applications.

With ongoing research, the implications of 1,2-dichlorobuta-1,3-diene continue to unfold, revealing its capacity to contribute valuable insights into various branches of chemistry.

1,4-Dichlorobuta-1,3-diene

Lastly, 1,4-dichlorobuta-1,3-diene showcases chlorine substitutions at both ends of the butadiene chain, creating interesting properties and behaviors:

  • Stability Analysis: Its terminal positions lead to distinct stability profiles when compared to other dichlorobutane isomers, allowing for focused studies on stability and reactivity.
  • Potential Uses in Agriculture: Compounds like this one are sometimes explored for applications in agrochemicals, offering alternative solutions in pest control.
  • Mechanical Properties: The structure may impart unique mechanical properties that are beneficial in specific applications, particularly in polymer sciences.

The study of 1,4-dichlorobuta-1,3-diene not only enriches our understanding of halogenated compounds but also contributes significantly to applied chemistry in industrial contexts.