Structure via PubChem · Public domain (PubChem)
mesitylene
Sign in to saveAlso known as 1,3,5-trimethylbenzene, symmetrical trimethylbenzene, sym-trimethylbenzene, 3,5-dimethyltoluene, s-trimethylbenzene
Mesitylene or 1,3,5-trimethylbenzene is a derivative of benzene with three methyl substituents positioned symmetrically around the ring. The other two isomeric trimethylbenzenes are 1,2,4-trimethylbenzene (pseudocumene) and 1,2,3-trimethylbenzene (hemimellitene). All three compounds have the formula C6H3(CH3)3, which is commonly abbreviated C6H3Me3. Mesitylene is a colorless liquid with sweet aromatic odor. It is a component of coal tar, which is its traditional source. It is a precursor to diverse fine chemicals. The mesityl group (Mes) is a substituent with the formula C6H2Me3 and is found i
Chemical data
- Formula
- C9H12
- Molecular weight
- 120.19 g/mol
- IUPAC name
- 1,3,5-trimethylbenzene
- SMILES
- CC1=CC(=CC(=C1)C)C
- InChIKey
- AUHZEENZYGFFBQ-UHFFFAOYSA-N
- XLogP
- 3.4
- Polar surface area
- 0 Ų
- H-bond donors
- 0
- H-bond acceptors
- 0
- Formal charge
- 0
via PubChem
Wikidata facts
- Mass
- 120.094
Show 13 more facts
- Commons category
- 1,3,5-Trimethylbenzene
- boiling point
- 329
- chemical formula
- C₉H₁₂
- NIOSH Pocket Guide ID
- 0639
- density
- 0.86
- melting point
- -44.7
- vapor pressure
- 2
- flash point
- 122
- solubility
- 0.002
- ionization energy
- 8.41
- time-weighted average exposure limit
- 125
- canonical SMILES
- CC1=CC(=CC(=C1)C)C
- electric dipole moment
- 0
via Wikidata · CC0
~5 min read
Article
8 sectionsContents
- Preparation
- Reactions
- Applications
- Niche uses
- History
- Mesityl group
- Safety and the environment
- References
Mesitylene or 1,3,5-trimethylbenzene is a derivative of benzene with three methyl substituents positioned symmetrically around the ring. The other two isomeric trimethylbenzenes are 1,2,4-trimethylbenzene (pseudocumene) and 1,2,3-trimethylbenzene (hemimellitene). All three compounds have the formula C6H3(CH3)3, which is commonly abbreviated C6H3Me3. Mesitylene is a colorless liquid with sweet aromatic odor. It is a component of coal tar, which is its traditional source. It is a precursor to diverse fine chemicals. The mesityl group (Mes) is a substituent with the formula C6H2Me3 and is found in various other compounds.
==Preparation== Mesitylene is prepared by transalkylation of xylene over solid acid catalyst: 2 C6H4(CH3)2 ⇌ C6H3(CH3)3 + C6H5CH3 C6H4(CH3)2 + CH3OH → C6H3(CH3)3 + H2O