67828-19-7

Basic information

• Product Name: 4-(4-methoxyphenyl)-3-methylbutan-2-one
• Synonyms: 4-(4-methoxyphenyl)-3-methylbutan-2-one;3-(4-Methoxybenzyl)-2-butanone;3-Methyl-4-(4-methoxyphenyl)-2-butanone;α-Methyl-4-methoxyphenethylmethyl ketone;2-Butanone, 4-(4-methoxyphenyl)-3-methyl-;3-Methyl-4-(4-methoxyphenyl)butan-2-one;Einecs 267-240-8
• CAS NO: 67828-19-7
• Molecular Formula: C₁₂H₁₆O₂
• Molecular Weight: 192.25424
• EINECS: 267-240-8
• Mol File: 67828-19-7.mol
• Article Data: 6

Chemical Properties

• Boiling Point: 282°Cat760mmHg
• Flash Point: 113.7°C
• Appearance: /
• Density: 0.994g/cm³
• Vapor Pressure: 0.00344mmHg at 25°C
• Refractive Index: 1.495
• CAS DataBase Reference: 4-(4-methoxyphenyl)-3-methylbutan-2-one(CAS DataBase Reference)
• NIST Chemistry Reference: 4-(4-methoxyphenyl)-3-methylbutan-2-one(67828-19-7)
• EPA Substance Registry System: 4-(4-methoxyphenyl)-3-methylbutan-2-one(67828-19-7)

Safety Data

• Hazardous Substances Data: 67828-19-7(Hazardous Substances Data)

Usage

General Description

The chemical 4-(4-methoxyphenyl)-3-methylbutan-2-one, also known as p-methoxyhydrocinnamaldehyde, is an organic compound with a molecular formula C12H16O2. It is a yellow to brown solid with a sweet, floral, and spicy scent. 4-(4-methoxyphenyl)-3-methylbutan-2-one is often used as a fragrance ingredient in perfumes and cosmetic products. It is also used in the food industry as a flavoring agent. Additionally, it has been studied for its potential medical applications, including antimicrobial and anti-inflammatory properties.

InChI:InChI=1/C12H16O2/c1-9(10(2)13)8-11-4-6-12(14-3)7-5-11/h4-7,9H,8H2,1-3H3

Upstream product

• 859194-32-4 2-(4-methoxy-benzyl)-2-methyl-acetoacetic acid ethyl ester 
• 814-78-8 3-Methyl-3-buten-2-one 
• 100-66-3 methoxybenzene 
• 36600-75-6 2-(4-methoxy-benzyl)-3-oxo-butyric acid ethyl ester 
• 2746-25-0 p-Methoxybenzyl bromide 
• 123-11-5 4-methoxy-benzaldehyde 
• 69390-19-8 (E)-3-methyl-4-(4-methoxyphenyl)-3-buten-2-one 

Downstream Products

• 100-09-4 4-methoxybenzoic acid 

Relevant articles and documents

Palladium-Catalyzed Decarboxylative Benzylation of Acetylides and Enolates

Benzylic alkylation of enolates and acetylides has been achieved through the use of a decarboxylative benzylation strategy. Previous research in this area is often limited by the need for extended conjugation in the electrophiles that are coupled. Herein, we report that the use of 1,1'-bis(diphenylphosphino)ferrocene (dppf) ligand allows the coupling of simple benzyl electrophiles with enolates, while the use of XPhos ligand promotes the decarboxylative couplings of propiolates.

Substrate scope and synthetic applications of the enantioselective reduction of α-alkyl-β-arylenones mediated by Old Yellow Enzymes

The ene-reductases mediated bioreduction of a selection of open-chain α-alkyl-β-aryl enones afforded the corresponding saturated α-chiral ketones in high yield and optical purity in several cases. The stereo-electronic requirements of the reaction have been investigated, considering the nature and location of substituents on the aromatic ring as well as the steric hindrance at the α-position and adjacent to the carbonyl functionality. The general considerations drawn allow us to guide the design of α,β-unsaturated ketones to be employed as substrates of ene-reductases in future preparative applications. An interesting case of orthogonality between enzyme-based and substrate-based stereocontrol within the highly homologous ene-reductases from Saccharomyces species (OYE1-3) has been reported and rationalized with the help of computational docking studies. Furthermore, to demonstrate the synthetic versatility of the reaction, the key chiral precursors of biologically active compounds such as (2′R)- stenusines and (S)-iopanoic acid were obtained. The very robust protocol allowed us to run the reactions on preparative scale in quantitative yields, with a simple work-up and no chromatographic purification steps. The Royal Society of Chemistry 2013.

Catalyzed Reactions of Enol Ethers with SN1 Active Groups: A Novel Method for the Preparation of α-Alkylated Ketones

The performance of tert-alkylations, alkoxyalkylations, and aldehyde enolate allylations proceeding with low catalyst loading (0.1 mol % - 5 mol %) is described. The reactions are complete within short times and can even be performed without solvent and under ambient conditions. The mechanism of the reaction was investigated by deuterium labeling and cross-over studies.