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Azobenzene

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Identification
Molecular formula
C14H14N2
CAS number
495-54-5
IUPAC name
(2,4-dimethylphenyl)-(o-tolyl)diazene
State
State

The compound is typically in a solid state at room temperature, existing as red-orange crystals or powder. It is stable under normal conditions but should be kept away from light to prevent degradation.

Melting point (Celsius)
186.00
Melting point (Kelvin)
459.15
Boiling point (Celsius)
340.00
Boiling point (Kelvin)
613.15
General information
Molecular weight
240.35g/mol
Molar mass
240.3510g/mol
Density
1.1033g/cm3
Appearence

(2,4-dimethylphenyl)-(o-tolyl)diazene appears as red-orange crystals or powder. It is insoluble in water but soluble in organic solvents such as ethanol and ether. This compound exhibits a bright color due to its azo group (-N=N-), which is responsible for absorbing light. The presence of methyl groups also contributes to a slightly altered coloration compared to unsubstituted azobenzene.

Comment on solubility

Solubility of (2,4-Dimethylphenyl)-(o-tolyl)diazene

The solubility of (2,4-dimethylphenyl)-(o-tolyl)diazene, a diazo compound, can be complex and is influenced by several factors. Due to its aromatic nature, the solubility is often characterized by non-polar interactions and limited polarization. Here are some key points regarding its solubility:

  • Solvent Characteristics: The compound is more likely to dissolve in non-polar solvents such as hexane or toluene, rather than in polar solvents like water.
  • Aromatic Structure: The presence of multiple aromatic rings tends to reduce solubility in polar solvents because of the increased hydrophobicity.
  • Temperature Influence: Higher temperatures may enhance solubility in certain solvents by providing the additional energy needed to overcome dispersion forces.
  • Concentration Effects: Due to its structure, at high concentrations, (2,4-dimethylphenyl)-(o-tolyl)diazene may precipitate out of solution, indicating a clear limit to its solubility.

In conclusion, while (2,4-dimethylphenyl)-(o-tolyl)diazene shows limited solubility in polar solvents, it is notably more soluble in non-polar environments. This behavior is typical for many diazo compounds, manifesting the importance of functional groups and molecular structure in influencing solubility.

Interesting facts

Interesting Facts About (2,4-dimethylphenyl)-(o-tolyl)diazene

(2,4-dimethylphenyl)-(o-tolyl)diazene is a fascinating compound in the realm of organic chemistry, particularly known for its unique structure and properties. Here are some compelling insights:

  • Diazene Functional Group: This compound features a diazene functional group (N=N) which is notable for its ability to undergo *isomerization*. This property can lead to different configurations, impacting its reactivity.
  • Substituent Effects: The presence of methyl groups in the 2 and 4 positions of the phenyl ring influences the electronic structure, which can enhance electron density and affect the compound's reactivity in chemical reactions.
  • Applications in Chemistry: Compounds like (2,4-dimethylphenyl)-(o-tolyl)diazene are often studied for their potential applications in organic synthesis, especially in creating dyes and pigments due to their vibrant colors.
  • Historical Significance: Diazenes have been studied since the 19th century, contributing valuable insights into the development of azo compounds, which are critical in the dye industry.
  • Thermodynamic Stability: Understanding the thermodynamics of diazene compounds can provide insights into their stability and reactivity, making them interesting subjects for research in thermochemistry.

This compound encapsulates the intriguing interplay between structure and reactivity, making it a valuable topic for further investigation by students and professionals alike. As chemists continue to explore the vast landscape of organic compounds, the understanding and utilization of diazenes like (2,4-dimethylphenyl)-(o-tolyl)diazene carry implications across both theoretical and practical chemistry.

Synonyms
2,2',4-TRIMETHYLAZOBENZENE
29418-23-3