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Ethyl acetoacetate

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Identification
Molecular formula
C12H12ClN3O3
CAS number
2243-76-7
IUPAC name
ethyl 2-(3-chlorophenyl)azo-3-oxo-butanoate
State
State

At room temperature, this compound is a solid. It generally presents as a powder or crystalline substance and may not be stable in air if exposed for extended durations, especially if moisture is present.

Melting point (Celsius)
122.00
Melting point (Kelvin)
395.15
Boiling point (Celsius)
211.00
Boiling point (Kelvin)
484.15
General information
Molecular weight
225.66g/mol
Molar mass
225.6610g/mol
Density
1.1710g/cm3
Appearence

Ethyl 2-(3-chlorophenyl)azo-3-oxo-butanoate appears as a red to dark orange crystalline solid. The compound is typically sensitive to light and might change color upon prolonged exposure. It is soluble in organic solvents like ethanol, methanol, and chloroform, but has limited solubility in water.

Comment on solubility

Solubility of Ethyl 2-(3-chlorophenyl)azo-3-oxo-butanoate

Ethyl 2-(3-chlorophenyl)azo-3-oxo-butanoate is a compound characterized by its unique azo functional group, which often influences its solubility properties. Below are key points regarding its solubility:

  • Polarity: The presence of both an ethyl ester group and an azo linkage affects the overall polarity of the molecule. Generally, polar compounds tend to be soluble in polar solvents.
  • Solvent Compatibility: It is likely soluble in organic solvents such as:
    • Ethyl acetate
    • Dichloromethane
    • Acetone
  • Water Solubility: The solubility in water may be limited due to its overall hydrophobic character, thus making it less soluble compared to more polar or ionic compounds.
  • Temperature Influence: Increasing the temperature may enhance solubility as the kinetic energy of the molecules increases, aiding in the dissolution process.
  • Chemical Interactions: Solubility might also be influenced by interactions with various solvents, such as hydrogen bonding or Van der Waals forces.

In summary, while ethyl 2-(3-chlorophenyl)azo-3-oxo-butanoate is expected to dissolve well in non-polar and slightly polar organic solvents, its solubility in water would likely remain minimal. Exploring solubility in different solvents can provide deeper insights into its chemical behavior and potential applications.

Interesting facts

Interesting Facts About Ethyl 2-(3-chlorophenyl)azo-3-oxo-butanoate

Ethyl 2-(3-chlorophenyl)azo-3-oxo-butanoate is a fascinating compound, primarily known for its application in the field of chemistry, particularly in the synthesis of azo dyes. Azo compounds are characterized by the presence of the functional group -N=N-, which contributes to their vibrant colors. Here are some engaging aspects of this compound:

  • Azo Chemistry: The azo group in this compound is instrumental in creating colored substances. It makes it a vital component in industries that produce dyes and pigments, which are used in textiles, printing, and even food coloring.
  • Pharmacological Significance: Compounds like ethyl 2-(3-chlorophenyl)azo-3-oxo-butanoate have been explored for various biological activities. Research has shown that some azo compounds can exhibit antibacterial and antifungal properties, making them of interest in pharmaceutical studies.
  • Structure-Activity Relationship (SAR): The incorporation of a 3-chlorophenyl group in its structure contributes to the overall reactivity of the compound, influencing its interaction with biological targets. The understanding of SAR plays a crucial role in the design of new pharmacological agents.
  • Applications in Organic Synthesis: Ethyl 2-(3-chlorophenyl)azo-3-oxo-butanoate also serves as an intermediate in organic synthesis, providing chemists with versatile pathways to create more complex molecules.

As we continue to explore the world of chemistry, compounds like ethyl 2-(3-chlorophenyl)azo-3-oxo-butanoate serve as prime examples of how molecular architecture can lead to diverse functionalities and applications across various fields. The study of such compounds not only deepens our understanding of chemical interactions but also contributes to advancements in technology, medicine, and materials science.

Synonyms
BRN 4485443
2-((m-Chlorophenyl)azo)-3-oxobutyric acid ethyl ester
3-Chlor-phenyl-azo-acetessigester [German]
5869-59-0
3-Chlor-phenyl-azo-acetessigester
Butanoic acid, 2-((3-chlorophenyl)azo)-3-oxo-, ethyl ester
ACETOACETIC ACID, 2-((m-CHLOROPHENYL)AZO)-, ETHYL ESTER