128839-68-9

Usage

Appearance

Colorless to pale yellow liquid.

Odor

Fruity.

Usage

Flavoring agent and fragrance ingredient in food and cosmetic industries.

Derivative

Ethyl ester of 2-(4-methylphenyl)propenoic acid.

Applications

Production of perfumes, soaps, and other personal care products.

Scent Characteristics

Sweet, floral, and fruity.

Fragrance Note

Often used as a top note in various fragrance compositions.

Industrial Use

Solvent in various industrial processes.

Upstream product

• 78925-99-2 ethyl 2-hydroxy-2-p-tolylpropionate 
• 5459-35-8 2-bromo-acrylic acid ethyl ester 
• 624-31-7 4-tolyl iodide 
• 106-38-7 para-bromotoluene 
• 50-00-0 formaldehyd 
• 14062-19-2 p-tolylacetic acid ethyl ester 
• 5524-56-1 ethyl 2-p-tolyl-2-oxoacetate 
• 62833-11-8 ethyl 3-hydroxy-2-(4-methylphenyl)acrylate 
• 4294-57-9 para-methylphenylmagnesium bromide 
• 1779-49-3 Methyltriphenylphosphonium bromide 
• 617-35-6 2-oxo-propionic acid ethyl ester 

Downstream Products

• 1346946-63-1 3-(2-p-tolylacryloyl)oxazolidin-2-one 
• 1346947-75-8 C₁₉H₁₉NO₃S 
• 938-94-3 (R,S)-2-(4'-methylphenyl) propionic acid 
• 78926-01-9 2-(4-methylphenyl)propanoic acid ethyl ester 
• 1629188-67-5 (2Z,4E)-ethyl 5-(4-chlorophenyl)-2-p-tolylpenta-2,4-dienoate 
• 1629188-68-6 (2E,4E)-ethyl 5-(4-chlorophenyl)-2-p-tolylpenta-2,4-dienoate 
• 66616-85-1 α-(4-methylphenyl)acrylic acid 
• 1264519-02-9 phenanthren-9-yl 2-p-tolylacrylate 

Relevant academic research and scientific papers

Facile synthesis of 2-arylpropenoic acid esters by cross-coupling using electrogenerated highly reactive zinc and a palladium catalyst

Highly reactive zinc metal was prepared by electrolysis of a DMF solution containing naphthalene and a supporting electrolyte in a one-compartment cell fitted with a platinum cathode and a zinc anode. The reaction of this reactive zinc with ethyl 2-bromoacrylate at -20 °C and the following cross-coupling reaction with aryl iodides in the presence of 5 mol% Pd(P(o-Tol)3)2Cl2 at 70 °C gave the corresponding ethyl 2-arylpropenoates in almost quantitative yields.

Discovery of novel akt1 inhibitor induces autophagy associated death in hepatocellular carcinoma cells

In this study, a series of thieno [2,3-d]pyrimidine derivatives were designed, synthesized and evaluated as novel AKT1 inhibitors. In vitro antitumor assay results showed that compounds 9d-g and 9i potently suppressed the enzymatic activities of AKT1 and

Iodonium Ylides as Carbene Precursors in Rh(III)-Catalyzed C-H Activation

The rhodium(III)-catalyzed coupling of C-H substrates with iodonium ylides has been realized for the efficient synthesis of diverse cyclic skeletons, where the iodonium ylides have been identified as efficient and outstanding carbene precursors. The reaction systems are applicable to both sp2 and sp3 C-H substrates under mild and redox-neutral conditions. The catalyst loading can be as low as 0.5 mol % in a gram-scale reaction. Representative products exhibit cytotoxicity toward human cancer cells at nanomolar levels.

A 1,3,2-Diazaphospholene-Catalyzed Reductive Claisen Rearrangement

1,3,2-Diazaphospholenes (DAPs) are an emerging class of organic hydrides. In this work, we exploited them as efficient catalysts for very mild reductive Claisen rearrangements. The method is tolerant towards a wide variety of functional groups and operates at ambient temperature. Besides being enantiospecific for substrates with existing stereogenic centers, the diastereoselectivity can be switched by varying solvents and DAP catalysts. The reaction kinetics show direct rearrangements of O-bound phospholene enolates and provide a proof-of-principle for catalytic enantioselective reactions.

Ruthenium-Catalyzed C-H Allylation of Alkenes with Allyl Alcohols via C-H Bond Activation in Aqueous Solution

A robust Ru(II)-catalyzed C-H allylation of electron-deficient alkenes with allyl alcohols in aqueous solution is reported. This method provides a straightforward and efficient access to the synthetically useful 1,4-diene skeletons. With the assistance of the N-methoxycarbamoyl directing group, this allylation reaction features a broad substrate scope with good functional group tolerance, excellent regio- and stereoselectivity, absence of metal oxidants, water-tolerant solvents, and mild reaction conditions. The mechanistic studies indicate that the process of the reversible C-H bond ruthenation is assisted by acetate, and the rate-determining step is unlikely to be the step of C-H bond cleavage.

Switchable C-H Functionalization of N-Tosyl Acrylamides with Acryloylsilanes

A controllable Rh-catalyzed protocol to access alkylation and alkenylation-annulation of N-tosyl acrylamide with acryloyl silane is reported. In contrast to the directing group or catalyst-dependent divergent sp2 C-H alkylation/alkenylation, the intrinsic property of acryloylsilane allows the switchable reaction manifold, thereby affording either alkylation or annulation products with slight modification of the reaction conditions.

Concise Synthesis of 2-Arylpropanoic Acids and Study of Unprecedented Reduction of 3-Hydroxy-2-arylpropenoic Acid Ethyl Ester to 2-Arylpropenoic Acid Ethyl Ester by BH3·THF

We have developed a concise method of synthesizing racemic arylpropanoic acids, which have been widely used as nonsteroidal anti-inflammatory drugs (NSAIDs). The synthesis involves only four steps from commercially available benzaldehyde. The synthesis incorporates an unprecedented reduction reaction, conversion of 3-hydroxy-2-arylpropenoic acid ethyl ester to 2-arylpropenoic acid ethyl ester by BH3·THF. The reduction reaction has been investigated and optimized.

Rhodium(iii)-catalyzed C-H allylation of electron-deficient alkenes with allyl acetates

Rhodium-catalyzed C-H allylation of acrylamides with allyl acetates is reported. The use of weakly coordinating directing group resulted in high reaction efficiency, broad functionality tolerance and excellent γ-selectivity, which opens a new synthetic pathway for the access of 1,4-diene skeletons.

Directing-group-assisted copper-catalyzed olefinic trifluoromethylation of electron-deficient alkenes

Assistance provided: The directing group in the title reaction not only activates the substrates but also allows the stereospecific formation of cis-trifluoromethylated products. The reaction is operationally simple and tolerates a wide variety of functional groups, thus providing an efficient method for the stereoselective synthesis of β-CF3-functionalized acrylamide derivatives. Copyright

Enantioselective enolate protonation in sulfamichael addition to r-substituted n-acryloyloxazolidin-2-ones with bifunctional organocatalyst

Organocatalytic conjugate addition of thiols to R-substituted N-acryloyloxazolidin-2-ones followed by asymmetric protonation has been studied in the presence of cinchona alkaloid derived thioureas. Both of the enantiomers are accessible with the same level of enantioselectivity using pseudoenantiomeric quinine/quinidine derived catalysts. The addition/protonation products have been converted to useful biologically active molecules. 2011 American Chemical Society.