80691-79-8

Basic information

• Product Name: 2-METHYLENE-3-PHENYL-BUTYRALDEHYDE
• Synonyms: 2-METHYLENE-3-PHENYL-BUTYRALDEHYDE;2-(alpha-methylbenzyl)acrylaldehyde;2-Methylene-3-phenylbutanal;β-Methyl-α-methylenebenzenepropanal
• CAS NO: 80691-79-8
• Molecular Formula: C₁₁H₁₂O
• Molecular Weight: 160.21238
• EINECS: 279-531-7
• Mol File: 80691-79-8.mol
• Article Data: 7

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 2-METHYLENE-3-PHENYL-BUTYRALDEHYDE(CAS DataBase Reference)
• NIST Chemistry Reference: 2-METHYLENE-3-PHENYL-BUTYRALDEHYDE(80691-79-8)
• EPA Substance Registry System: 2-METHYLENE-3-PHENYL-BUTYRALDEHYDE(80691-79-8)

Safety Data

• Hazardous Substances Data: 80691-79-8(Hazardous Substances Data)

Upstream product

• 16251-77-7 3-Phenylbutyraldehyde 
• 80691-80-1 2-(1-phenylethyl)propane-1,3-diol 
• 1115-11-3 2-methyl-2-pentenal 
• 98-80-6 phenylboronic acid 
• 2722-36-3 3-phenyl-1-butanol 
• 50-00-0 formaldehyd 

Downstream Products

• 1235457-91-6 (S)-2-((R)-1-phenylethyl)oxirane-2-carbaldehyde 
• 97416-75-6 2-methyl-3-phenylbutanal 
• 1323440-92-1 (Z)-triethyl((2-methyl-3-phenylbut-1-en-1-yl)oxy)silane 

Relevant articles and documents

The cinchona primary amine-catalyzed asymmetric epoxidation and hydroperoxidation of α,β-unsaturated carbonyl compounds with hydrogen peroxide

Using cinchona alkaloid-derived primary amines as catalysts and aqueous hydrogen peroxide as the oxidant, we have developed highly enantioselective Weitz-Scheffer-type epoxidation and hydroperoxidation reactions of α,β-unsaturated carbonyl compounds (up to 99.5:0.5 er). In this article, we present our full studies on this family of reactions, employing acyclic enones, 5-15-membered cyclic enones, and α-branched enals as substrates. In addition to an expanded scope, synthetic applications of the products are presented. We also report detailed mechanistic investigations of the catalytic intermediates, structure-activity relationships of the cinchona amine catalyst, and rationalization of the absolute stereoselectivity by NMR spectroscopic studies and DFT calculations.

Rapid organocatalytic aldehyde-aldehyde condensation reactions

We report the results of the systematic optimization of the α-methylenation of aldehydes with aqueous formaldehyde. A simple combination of a secondary amine catalyst and a weak acid co-catalyst has been identified, allowing access to α-substituted acroleins in a matter of minutes. In the absence of formaldehyde, the catalytic system promoted the self-condensation reaction of α,β-unsaturated aldehydes. Both of these reactions exhibited linear relationships between co-catalyst acidities and reaction rates. A second-order dependence of catalyst concentration was observed, pointing to the involvement of two molecules of the ammonium catalyst in the rate-determining step. Wiley-VCH Verlag GmbH & Co. KGaA, 2007.

Mild organocatalytic α-methylenation of aldehydes

A rapid and extremely convenient method for α-methylenation of aldehydes with aqueous formaldehyde is described. Two optimal catalytic systems are presented that allow short reaction times and afford the functionalized products in good to excellent yields (up to 99%) and chemoselectivity.