{{short description|Chemical compound}} {{chembox | Name = Mesitaldehyde | ImageFile = Mesitaldehyde.svg | ImageClass = skin-invert | OtherNames = {{ubl|2-Formylmesitylene|2-Mesitylenecarboxaldehyde|Aldehydomesitylene|2,4,6-Trimethylbenzaldehyde|Isodural|Mesitaldehyde|Mesityl aldehyde|Mesitylenecarboxaldehyde}} | IUPACName = 2,4,6-Trimethylbenzaldehyde | Section1 = {{Chembox Identifiers | CASNo = 487-68-3 | ChEBI = 195893 | ChEMBL = 3560744 | ChemSpiderID = CU8500000 |DTXSID = DTXSID5052125 | EC_number = 207-662-1<ref name="ECHA 2023 t464">{{cite web | title=Substance Information | website=ECHA | date=2023-05-19 | url=https://echa.europa.eu/substance-information/-/substanceinfo/100.006.966 | access-date=2024-04-09}}</ref> | InChI = 1S/C10H12O/c1-7-4-8(2)10(6-11)9(3)5-7/h4-6H,1-3H3 |InChIKey = HIKRJHFHGKZKRI-UHFFFAOYSA-N | PubChem = 10254 | SMILES = CC1=CC(=C(C(=C1)C)C=O)C }} | Section2 = {{Chembox Properties | AtmosphericOHRateConstant = | Appearance = Clear colorless to light yellow liquid | BoilingPtC = 238.50 | Density = 1.018 g/mL at 20 °C | C = 10 | H = 12 | O =1 | HenryConstant = | LogP = | MeltingPtC = 14 |Odour = Pungent | pKa = | pKb = | Solubility = | SolubleOther = | Solvent = | VaporPressure = }} | Section7 = {{Chembox Hazards | AutoignitionPt = | ExploLimits = | FlashPtC = 105.6 | LD50 = | LC50 = | MainHazards = | NFPA-H = | NFPA-F = | NFPA-I = | NFPA-S = | PEL = | REL = | ExternalSDS = | GHSPictograms = {{GHS07}}{{GHS09}} | GHSSignalWord = Warning | HPhrases = {{H-phrases|H315|H319|H335}} | PPhrases = {{P-phrases|P280|P305+P351+P338}} }} }}
'''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.
==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.<ref>{{Cite web |title=Mesitaldehyde, 97%, Thermo Scientific Chemicals, Quantity: 10 g {{!}} Fisher Scientific |url=https://www.fishersci.com/shop/products/mesitaldehyde-97-thermo-scientific/AC125570100 |access-date=2024-04-11 |website=www.fishersci.com}}</ref><ref name="KIRSCHFELD MUTHUSAMY SANDER 1995 p. ">{{cite journal | last1=KIRSCHFELD | first1=A. | last2=MUTHUSAMY | first2=S. | last3=SANDER | first3=W. | title=ChemInform Abstract: Dimesityldioxirane (II): A Dioxirane Stable in the Solid State. | journal=ChemInform | publisher=Wiley | volume=26 | issue=17 | date=1995-04-25 | issn=0931-7597 | doi=10.1002/chin.199517113 | page=}}</ref>
==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 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.<ref name="Organic Syntheses 1967 p. 1">{{cite journal | title=Aromatic Aldehydes. Mesitaldehyde | journal=Organic Syntheses | volume=47 | date=1967 | doi=10.15227/orgsyn.047.0001 | page=1 }}</ref>
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== *Mesitylene
==References== {{reflist}}
Category:Benzaldehydes