6658-48-6

Basic information

• Product Name: P-ISOBUTYL-ALPHA-METHYLHYDROCINNAMALDEHYDE
• Synonyms: P-ISOBUTYL-ALPHA-METHYLHYDROCINNAMALDEHYDE;3-(p-Cumenyl)-2-methylpropionaldehyd;Rhodial;α-Methyl-4-(2-methylpropyl)benzenepropanal;4-ISOBUTYL-ALPHA-METHYLHYDROCINNAMALDEHYDE
• CAS NO: 6658-48-6
• Molecular Formula: C₁₄H₂₀O
• Molecular Weight: 204.31
• EINECS: 229-695-0
• Mol File: 6658-48-6.mol
• Article Data: 4

Chemical Properties

• Boiling Point: 285.4 °C at 760 mmHg
• Flash Point: 127.5 °C
• Appearance: Colorless liquid
• Density: 0.932 g/cm³
• Vapor Pressure: 0.0028mmHg at 25°C
• Refractive Index: 1.495
• Water Solubility: 2.76mg/L at 25℃
• CAS DataBase Reference: P-ISOBUTYL-ALPHA-METHYLHYDROCINNAMALDEHYDE(CAS DataBase Reference)
• NIST Chemistry Reference: P-ISOBUTYL-ALPHA-METHYLHYDROCINNAMALDEHYDE(6658-48-6)
• EPA Substance Registry System: P-ISOBUTYL-ALPHA-METHYLHYDROCINNAMALDEHYDE(6658-48-6)

Safety Data

• Hazardous Substances Data: 6658-48-6(Hazardous Substances Data)

Usage

Chemical Properties

P-ISOBUTYL-ALPHA-METHYLHYDROCINNAMALDEHYDE is a colorless liquid with a powerful, fresh, floralmuguet- like note. It is recommended as an alternative to the preceding aldehyde. As described earlier, the material can be produced starting from the corresponding benzaldehyde, which is available, for example, by formylation of isobutylbenzene.

Flammability and Explosibility

Flammable

Trade name

Silvial? (Givaudan).

InChI:InChI=1/C14H20O/c1-11(2)8-13-4-6-14(7-5-13)9-12(3)10-15/h4-7,10-12H,8-9H2,1-3H3

Upstream product

• 40150-98-9 4-(2-methyl-1-propyl)benzaldehyde 
• 538-93-2 1-phenyl-2-methylpropane 

Relevant articles and documents

A synthetic route to 4-alkyl-α-methylhydrocinnamylaldehydes

The 4-Alkyl-α-methylhydrocinnamylaldehydes (alkyl-isopropyl, isobutyl, methyl) are frequently used fragrances with desired floral (lilac, cyclamen, lily-of-the-valley) scent. These substances are valued for their good stability in basic solution and, therefore, are frequently used in soaps, detergents, or shampoos. These substances are synthesized by a two-step synthesis involving base catalyzed aldol condensation of 4-alkylbenzaldehyde with propanal followed by selective hydrogenation of the C=C bond. In aldol condensation, selectivity is decreased by formation of undesired products of propanal autocondensation 2-methylpent-2-enal. In this work the reaction conditions for homogenous catalyzed aldol condensation of 4-isobutylbenzadehyde with propanal were tested (catalyst type and amount, molar ratio of reactants, solvent type). Reaction conditions giving the best results (92% conversion, 79% selectivity) were adapted to other 4-alkyl-α-methylcinnamylaldehydes preparation with similar results. In the second step—hydrogenation of aldol product different types of catalyst (nickel, cobalt, palladium or Adkins catalyst), and also different solvents, were tested. Hydrogenation conditions leading to the highest yield (72% selectivity at 95% conversion) were adapted to other 4-alkylhydrocinnamyladehydes with similar results.

LILIAN SURROGATE

Due to toxicological concerns, it may be desirable to replace the fragrance compound lilial with less problematic compounds without losing the creative power and quality regarding perfumes. The present invention addresses this need by using selected oxazolidines described herein.