13586-68-0

Basic information

• Product Name: p-tert-butyl-2-methylcinnamaldehyde
• Synonyms: p-tert-butyl-2-methylcinnamaldehyde;4-TERT-BUTYL CINNAMALDEHYDE;3,4-(1,1-DIMETHYLETHYL)PHENYL-2-METHYL-2-PROPENAL;4-tert-Butyl-ALPHA-methylcinnamaldehyde;3-[4-(1,1-Dimethylethyl)phenyl]-2-methylpropenal
• CAS NO: 13586-68-0
• Molecular Formula: C₁₄H₁₈O
• Molecular Weight: 202.29212
• EINECS: 237-014-3
• Mol File: 13586-68-0.mol
• Article Data: 6

Chemical Properties

• Boiling Point: 300.8°Cat760mmHg
• Flash Point: 125.2°C
• Appearance: /
• Density: 0.959g/cm³
• Vapor Pressure: 0.00109mmHg at 25°C
• Refractive Index: 1.53
• CAS DataBase Reference: p-tert-butyl-2-methylcinnamaldehyde(CAS DataBase Reference)
• NIST Chemistry Reference: p-tert-butyl-2-methylcinnamaldehyde(13586-68-0)
• EPA Substance Registry System: p-tert-butyl-2-methylcinnamaldehyde(13586-68-0)

Safety Data

• Hazardous Substances Data: 13586-68-0(Hazardous Substances Data)

Usage

Description

p-tert-butyl-2-methylcinnamaldehyde is a chemical compound belonging to the aldehyde class, characterized by its yellow liquid form and a strong, long-lasting sweet and floral scent. It is recognized for its stability under normal conditions, although it requires careful storage away from direct sunlight and ignition sources to maintain its integrity.

Uses

Used in Fragrance Industry:
p-tert-butyl-2-methylcinnamaldehyde is used as a fragrance ingredient for its distinctive sweet and floral scent, contributing to the creation of various perfumes and scented products.
Used in Chemical Synthesis:
In the chemical industry, p-tert-butyl-2-methylcinnamaldehyde serves as a key component in the synthesis of other chemicals, highlighting its versatility and importance in compound development.

InChI:InChI=1/C14H18O/c1-11(10-15)9-12-5-7-13(8-6-12)14(2,3)4/h5-10H,1-4H3/b11-9+

Upstream product

• 939-97-9 4-tert-Butylbenzaldehyde 
• 123-38-6 propionaldehyde 
• 691370-35-1 N-(4-tert-butylbenzylidene)-4-methylbenzenesulfonamide 
• 107-18-6 allyl alcohol 

Downstream Products

• 67306-03-0 Fenpropimorph 
• 1217269-88-9 (E)-1-(4-tert-butylphenyl)-2-methylhexa-1,5-dien-3-ol 
• 56107-04-1 3-(p-tert-butylphenyl)-2-methyl-1-propanol 
• 80-54-6 lilial 
• 37900-80-4 p-tert-butyl-β-methyl-3-phenylprop-2-en-1-ol 
• 1207338-26-8 (1E,2E)-3-(4-tert-butylphenyl)-2-methylacrylaldehyde oxime 

Relevant articles and documents

One-pot multistep synthetic strategies for the production of fenpropimorph using an ionic liquid solvent

The one-pot synthesis of the fungicide fenpropimorph has been achieved using two different synthetic strategies in an ionic liquid. The first pathway consists of a Heck coupling followed by reductive animation; the second pathway consists of an aldol condensation followed by hydrogenation/reductive animation. Homogeneous and heterogeneous palladium catalysts have been utilised in the ionic liquid to provide a catalyst/solvent system that is suitable for recycling and process optimisation.

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.

CONTINUOUS METHOD FOR PRODUCTION OF CINNAMALDEHYDE AND DIHYDROCINNAMALDEHYDE DERIVATIVES

The present invention relates to a continuous process for the preparation of cinnamaldehyde or cinnamaldehyde derivatives by continuous reaction of benzaldehyde derivatives with alkanals in the presence of bases and optionally subsequent continuous hydrogenation in a circulation reactor in the presence of a suspension catalyst and hydrogen to give dihydrocinnamaldehyde derivatives.