Mesitaldehyde or mesitylaldehyde is a colorless aromatic aldehyde. It is a liquid with a characteristic odor. It is commonly used as a precursor in the synthesis of various organic compounds, including pharmaceuticals, fragrances, and dyes.

Mesitaldehyde
Names
IUPAC name
2,4,6-Trimethylbenzaldehyde
Other names
  • 2-Formylmesitylene
  • 2-Mesitylenecarboxaldehyde
  • Aldehydomesitylene
  • 2,4,6-Trimethylbenzaldehyde
  • Isodural
  • Mesitaldehyde
  • Mesityl aldehyde
  • Mesitylenecarboxaldehyde
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.006.966 Edit this at Wikidata
EC Number
  • InChI=1S/C10H12O/c1-7-4-8(2)10(6-11)9(3)5-7/h4-6H,1-3H3
    Key: HIKRJHFHGKZKRI-UHFFFAOYSA-N
  • CC1=CC(=C(C(=C1)C)C=O)C
Properties
C10H12O
Molar mass 148.205 g·mol−1
Appearance Clear colorless to light yellow liquid
Odor Pungent
Density 1.018 g/mL at 20 °C
Melting point 14 °C (57 °F; 287 K)
Boiling point 238.50 °C (461.30 °F; 511.65 K)
Hazards
GHS labelling:
GHS07: Exclamation markGHS09: Environmental hazard
Warning
H315, H319, H335
P280, P305+P351+P338
Flash point 105.6 °C (222.1 °F; 378.8 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Properties

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Mesitaldehyde is a derivative of benzaldehyde, with three methyl groups attached to the benzene ring at positions 2, 4, and 6. This substitution with electron-donating methyl groups activates the aromatic ring for further electrophilic substitution reactions. Due to the hydrophobicity of the methyl groups, it is less soluble in water but more soluble in organic solvents. It is stable at ordinary temperatures.[2][3]

Synthesis and uses

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Mesitaldehyde is synthesized through the oxidation of mesitylene in acidic medium, typically using oxidants like chromium trioxide or potassium permanganate, followed by purification steps to isolate the aldehyde. It can also be prepared by formylation of mesitylene by reacting Mesitylene with a formyl group source such as paraformaldehyde or DMF (N,N-dimethylformamide) under specific conditions with a suitable catalyst. There are many other methods such as oxidation of acetylmesitylene by potassium permanganate, reduction of mesitoyl chloride, reaction of mesityllithum with iron pentacarbonyl, etc.[4]

It is primarily used as an intermediate in organic synthesis for various products such as pharmaceuticals, dyes, and fragrances. Due to its reactive nature, mesitaldehyde itself isn't likely the final drug molecule in medications.

See also

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References

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  1. ^ "Substance Information". ECHA. 2023-05-19. Retrieved 2024-04-09.
  2. ^ "Mesitaldehyde, 97%, Thermo Scientific Chemicals, Quantity: 10 g | Fisher Scientific". www.fishersci.com. Retrieved 2024-04-11.
  3. ^ KIRSCHFELD, A.; MUTHUSAMY, S.; SANDER, W. (1995-04-25). "ChemInform Abstract: Dimesityldioxirane (II): A Dioxirane Stable in the Solid State". ChemInform. 26 (17). Wiley. doi:10.1002/chin.199517113. ISSN 0931-7597.
  4. ^ "Aromatic Aldehydes. Mesitaldehyde". Organic Syntheses. 47: 1. 1967. doi:10.15227/orgsyn.047.0001.