Mesitaldehyde
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IUPAC name
2,4,6-Trimethylbenzaldehyde
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Other names
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Identifiers | |
3D model (JSmol)
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ChEBI | |
ChEMBL | |
ChemSpider | |
ECHA InfoCard | 100.006.966 |
EC Number |
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PubChem CID
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CompTox Dashboard (EPA)
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Properties | |
C10H12O | |
Molar mass | 148.20 g/mol |
Appearance | Clear colorless to light yellow liquid |
Odor | Pungent |
Density | 1.018 g/mL at 20 °C |
Melting point | 14 °C |
Boiling point | 238.50 °C (461.30 °F; 511.65 K) |
Hazards | |
GHS labelling: | |
Warning | |
H315, H319, H335 | |
P280, P305+P351+P338 | |
Flash point | 105.6 °C |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Mesitaldehyde or Mesitylaldehyde is a colourless 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.
Properties
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
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 like paraformaldehyde or DMF (N,N-Dimethylformamide) under specific conditions with a suitable catalyst.There are many other methods like 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 like pharmaceuticals, dyes, and fragrances. Due to its reactive nature, mesitaldehyde itself isn't likely the final drug molecule in medications.
See also
References
- ^ "Substance Information". ECHA. 2023-05-19. Retrieved 2024-04-09.
- ^ "Mesitaldehyde, 97%, Thermo Scientific Chemicals, Quantity: 10 g | Fisher Scientific". www.fishersci.com. Retrieved 2024-04-11.
- ^ 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.
- ^ "Aromatic Aldehydes. Mesitaldehyde". Organic Syntheses. 47: 1. 1967. doi:10.15227/orgsyn.047.0001.