Mesitylene
[CAS# 108-67-8]

Identification

• Classification: Organic raw materials >> Hydrocarbon compounds and their derivatives >> Aromatic hydrocarbon
• Name: Mesitylene
• Synonyms: 1,3,5-Trimethylbenzene
• Molecular Formula: C₉H₁₂
• Molecular Weight: 120.19
• CAS Registry Number: 108-67-8
• EC Number: 203-604-4
• SMILES: CC1=CC(=CC(=C1)C)C

Properties

• Density: 0.864
• Melting point: -45 °C
• Boiling point: 163-166 °C
• Refractive index: 1.498-1.5
• Flash point: 44 °C
• Water solubility: 2.9 g/L (20 °C)

Safety Data

• Hazard Symbols: GHS02;GHS07;GHS08;GHS09 Danger
• Risk Statements: H226-H304-H315-H319-H335-H411
• Safety Statements: P210-P233-P240-P241-P242-P243-P261-P264-P264+P265-P271-P273-P280-P301+P316-P302+P352-P303+P361+P353-P304+P340-P305+P351+P338-P319-P321-P331-P332+P317-P337+P317-P362+P364-P370+P378-P391-P403+P233-P403+P235-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Flammable liquids	Flam. Liq.	3	H226
Specific target organ toxicity - single exposure	STOT SE	3	H335
Chronic hazardous to the aquatic environment	Aquatic Chronic	2	H411
Skin irritation	Skin Irrit.	2	H315
Eye irritation	Eye Irrit.	2	H319
Aspiration hazard	Asp. Tox.	1	H304
Specific target organ toxicity - single exposure	STOT SE	3	H336
Specific target organ toxicity - repeated exposure	STOT RE	1	H372

• Transport Information: UN 2325

Discovery and Applications

Mesitylene, also known as 1,3,5-trimethylbenzene, is an aromatic hydrocarbon with the molecular formula C9H12. It was first synthesized in 1837 by the German chemist Robert Kane through the acid-catalyzed condensation of acetone. The name ""mesitylene"" is derived from ""mesityl,"" which refers to the Greek word ""mesos,"" meaning ""middle,"" due to its symmetrical structure with three methyl groups attached to a benzene ring at positions 1, 3, and 5. This discovery was significant in the study of aromatic compounds and provided insights into the chemistry of substituted benzenes, contributing to the broader understanding of organic chemistry.

Mesitylene is commonly used as a solvent in chemical synthesis and industrial processes. Its high boiling point (165°C) and ability to dissolve a wide range of organic compounds make it an ideal solvent for reactions requiring high temperatures.

As an intermediate, mesitylene is employed in the production of various chemicals. Its methyl groups can be selectively modified to introduce different functional groups, making it a valuable starting material for synthesizing dyes, resins, and polymers. For instance, mesitylene is used in the synthesis of trimellitic anhydride, which is an important intermediate for producing high-performance polymers and plasticizers.

Mesitylene is used as a standard in calibration for gas chromatography and mass spectrometry due to its stable and well-defined properties. It serves as a reference compound to ensure the accuracy and precision of analytical instruments.

In the petrochemical industry, mesitylene is used as a component in high-octane gasoline and jet fuels. Its high octane rating improves the performance and efficiency of engines by reducing knocking and enhancing combustion. Additionally, mesitylene's chemical stability under extreme conditions makes it a suitable additive for fuels used in aerospace and military applications.

Mesitylene is used in the formulation of specialty coatings and inks, where its solvent properties help achieve the desired viscosity and drying characteristics. It is particularly useful in applications requiring high thermal stability and chemical resistance, such as in automotive coatings and electronic component encapsulation.

References

2024. Cryogenic mesitylene-based moderator as an optimum solution for use in a DARIA compact neutron source. Atomic Energy.
DOI: 10.1007/s10512-024-01100-z

2010. Electronic structure of 9-mesityl-10-methylacridinium in ground and excited states: charge-shift mechanism introduced by counter anion shift. Physical Chemistry Chemical Physics.
DOI: 10.1039/c0cp00491j

2003. Syntheses, Structures, and Properties of Intercalation Compounds of Silver(I) Complex with [2.2]Paracyclophane. Inorganic Chemistry.
DOI: 10.1021/ic0302433