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Ethyl 2-(m-tolylazo)acetoacetate

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Identification
Molecular formula
C13H14N2O3
CAS number
92-81-9
IUPAC name
ethyl 2-(m-tolylazo)-3-oxo-butanoate
State
State

Ethyl 2-(m-tolylazo)acetoacetate is a solid at room temperature. It typically exists in its crystalline form and maintains its structural integrity under standard conditions.

Melting point (Celsius)
73.00
Melting point (Kelvin)
346.15
Boiling point (Celsius)
375.00
Boiling point (Kelvin)
648.15
General information
Molecular weight
234.27g/mol
Molar mass
234.2690g/mol
Density
1.1186g/cm3
Appearence

Ethyl 2-(m-tolylazo)acetoacetate appears as an orange to reddish-orange crystalline solid. The compound exhibits a characteristic azo group which often imparts vivid colors to the compound. It is typically used in dyes and pigments due to its bright and intense coloration.

Comment on solubility

Solubility of Ethyl 2-(m-tolylazo)-3-oxo-butanoate

Ethyl 2-(m-tolylazo)-3-oxo-butanoate, with its intriguing structure, showcases specific solubility characteristics that are noteworthy in various solvents. The solubility of this compound largely depends on the presence of polar and non-polar functional groups within its molecular architecture.

Solubility Characteristics:

  • Polar Solvents: The ethyl group can exhibit solubility in polar solvents like ethanol and methanol due to its capacity for hydrogen bonding.
  • Non-Polar Solvents: Conversely, non-polar solvents such as hexane may not effectively dissolve this compound because of its relatively polar character derived from the carbonyl group.
  • Aqueous Solubility: In terms of solubility in water, it is likely low due to the hydrophobic m-tolylazo moiety, which tends to resist solvation in polar environments.

The balance between hydrophilic and hydrophobic properties makes the solubility of ethyl 2-(m-tolylazo)-3-oxo-butanoate particularly interesting. As it is often the case with azo compounds, structural modifications may significantly enhance or reduce their solubility profile.

Remember, when considering solubility, it is vital to evaluate the surrounding conditions, such as temperature and potential additives, as these factors can dramatically influence the overall solubility behavior of the compound.

Interesting facts

Interesting Facts about Ethyl 2-(m-Tolylazo)-3-oxo-butanoate

Ethyl 2-(m-tolylazo)-3-oxo-butanoate is a fascinating compound that combines elements of organic chemistry with applications in various fields. Here are some noteworthy aspects:

  • Versatile Applications: This compound finds utility in areas such as dyeing processes and as an intermediate in the synthesis of pharmaceuticals due to its azo group, which often imparts color.
  • Synthetic Pathways: The synthesis of this compound involves the coupling of m-toluidine with an appropriate carbonyl compound, showcasing the importance of azo coupling reactions in organic synthesis.
  • Biological Activity: Compounds with azo groups, like ethyl 2-(m-tolylazo)-3-oxo-butanoate, have been studied for their potential biological activities, including antibacterial and antifungal properties.
  • Colorimetric Properties: Due to the presence of the azo group, this compound may exhibit color change under different pH conditions, making it useful as a pH indicator in analytical chemistry.
  • Environmental Considerations: As with many azo compounds, it’s essential to consider the environmental impact and toxicity, especially since some azo dyes can break down into harmful amines under certain conditions.

In summary, ethyl 2-(m-tolylazo)-3-oxo-butanoate serves as an excellent example of how organic chemistry intersects with practical applications, as well as the considerations that come with the use of such compounds in science and industry.

Synonyms
BRN 5052702
3-Oxo-2-(m-tolylazo)butyric acid ethyl ester
3-Tolyl-azo-acetessigester [German]
5869-57-8
3-Tolyl-azo-acetessigester
ACETOACETIC ACID, 2-(m-TOLYLAZO)-, ETHYL ESTER
Butanoic acid, 2-((3-methylphenyl)azo)-3-oxo-, ethyl ester