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Mesitylene

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Identification
Molecular formula
C9H12
CAS number
108-67-8
IUPAC name
mesitylene;1,2,3-trimethylbenzene;1,2,4-trimethylbenzene
State
State

At room temperature, mesitylene is in the liquid state, commonly used as a solvent or an intermediate in organic synthesis.

Melting point (Celsius)
-44.00
Melting point (Kelvin)
229.20
Boiling point (Celsius)
164.70
Boiling point (Kelvin)
437.90
General information
Molecular weight
120.19g/mol
Molar mass
120.1940g/mol
Density
0.8650g/cm3
Appearence

Mesitylene appears as a clear, colorless liquid with a distinctive aromatic odor. It is a derivative of benzene with three methyl groups, giving it a higher electron density.

Comment on solubility

Solubility of Mesitylene (1,2,3-trimethylbenzene and 1,2,4-trimethylbenzene)

Mesitylene, which includes both 1,2,3-trimethylbenzene and 1,2,4-trimethylbenzene, displays interesting solubility characteristics that contribute to its practical applications in various chemical processes.

Key Solubility Features:

  • Mesitylene is primarily soluble in non-polar solvents, highlighting its hydrophobic nature.
  • It has low solubility in water, making it less suitable for aqueous applications.
  • This compound can dissolve in organic solvents such as hexane, benzene, and chloroform.

Due to its structure, the presence of three methyl groups enhances its lipophilicity, further reducing its interaction with polar solvents. The low water solubility is significant in contexts where mesitylene is utilized, as it may form layers rather than mix uniformly in aqueous environments.

In summary, the solubility of mesitylene can be described as:

  • Non-polar: High solubility in non-polar solvents
  • Aqueous solution: Minimal solubility in water
  • Implications: Useful in applications where separation from water is advantageous

As a result, understanding the solubility of mesitylene is crucial for its safe handling and effective use in organic synthesis and industry.

Interesting facts

Interesting Facts about Mesitylene

Mesitylene, also known as 1,3,5-trimethylbenzene, is a fascinating aromatic hydrocarbon that has captured the interest of chemists and researchers alike. Here are some interesting aspects of this compound:

  • Unique Structure: Mesitylene features a benzene ring with three methyl groups attached at the 1, 3, and 5 positions, highlighting its symmetrical nature.
  • Versatile Solvent: Due to its nonpolar characteristics, mesitylene is commonly employed as a solvent in various chemical reactions and processes. It is especially useful in organic synthesis.
  • Industrial Application: Mesitylene is utilized in the production of certain polymers and resins, enhancing their properties and acting as a building block for various chemical syntheses.
  • Occurrence: This compound is often found in coal tar and petroleum, where it is formed as a byproduct during the distillation of organic materials.
  • Health and Safety: While mesitylene is a valuable compound in laboratories, it is essential to handle it with care, as inhalation or prolonged exposure can lead to respiratory issues.

Chemical Reactions

Mesitylene also participates in several chemical reactions, showcasing its versatility:

  • Electrophilic Substitution: It readily undergoes electrophilic substitution reactions due to the electron-donating nature of the methyl groups.
  • Oxidation: Mesitylene can be oxidized to produce various products, including mesityl oxide, which has applications in organic synthesis.

In summary, mesitylene is not just another aromatic hydrocarbon; its unique properties and versatility make it a vital component in many chemical processes and applications. Its study continues to inspire chemists exploring new realms of organic chemistry.

Synonyms
SCHEMBL323096