50415-73-1

Basic information

• Product Name: METHYL 4-METHOXYPHENYLACETATE
• Synonyms: 4-METHOXYPHENYLACETIC ACID METHYL ESTER;AURORA KA-6001;ASISCHEM D13374;METHYL 4-METHOXYPHENYLACETATE;METHYL P-METHOXYPHENYLACETATE;METHYL PARA METHOXYL PHENYLACETATE;ethyl 2-(4-Methoxyphenyl)propanoate;METHYL 2-(4-METHOXYPHENYL)PROPANOATE(WX618142)
• CAS NO: 50415-73-1
• Molecular Formula: C₁₁H₁₄O₃
• Molecular Weight: 180.2
• EINECS: 245-886-1
• Mol File: 50415-73-1.mol

Chemical Properties

• Boiling Point: 158 °C19 mm Hg(lit.)
• Flash Point: 98 °F
• Appearance: yellow-green/liquid
• Density: 1.135 g/mL at 25 °C(lit.)
• Refractive Index: n20/D 1.516(lit.)
• CAS DataBase Reference: METHYL 4-METHOXYPHENYLACETATE(CAS DataBase Reference)
• NIST Chemistry Reference: METHYL 4-METHOXYPHENYLACETATE(50415-73-1)
• EPA Substance Registry System: METHYL 4-METHOXYPHENYLACETATE(50415-73-1)

Safety Data

• Statements: 10
• Safety Statements: 16
• RIDADR: UN 3272 3/PG 3
• WGK Germany: 3
• F: 10
• Hazardous Substances Data: 50415-73-1(Hazardous Substances Data)

Usage

Synthesis Reference(s)

Journal of the American Chemical Society, 72, p. 5163, 1950 DOI: 10.1021/ja01167a101Synthesis, p. 231, 1984 DOI: 10.1055/s-1984-30784Tetrahedron Letters, 22, p. 4305, 1981 DOI: 10.1016/S0040-4039(01)82941-5Tetrahedron Letters, 35, p. 133, 1994 DOI: 10.1016/0040-4039(94)88182-0

Upstream product

• 67-56-1 methanol 
• 21086-33-9 2-bromo-1-(4-methoxyphenyl)-1-propanone 
• 83022-34-8 2-Hydroxy-4'-methoxypropiophenone dimethylacetal 
• 81112-07-4 2-chloro-1-(4'-methoxyphenyl)-propan-1-one 
• 121-97-1 4-Methoxypropiophenone 
• 149-73-5 trimethyl orthoformate 
• 58889-89-7 (Z)-1-methoxy-1-(4-methoxyphenyl)-1-propene 
• 115943-56-1 1,1-dimethoxy-1-(p-methoxyphenyl)propane 
• 104-92-7 1-bromo-4-methoxy-benzene 
• 17639-93-9 2-chloro-propionic acid methyl ester 
• 65784-33-0 methyl 2-(4-hydroxyphenyl)propanoate 
• 637-69-4 4-Methoxystyrene 
• 124-38-9 carbon dioxide 
• 201230-82-2 carbon monoxide 

Downstream Products

• 50415-73-1 methyl (R)-2-(4-methoxyphenyl)propionate 
• 111197-94-5 methyl (S)-2-(4-methyoxyphenyl)propionate 
• 942-54-1 2-(4-methoxyphenyl)propanoic acid 
• 4842-49-3 (R)-2-(4-methoxyphenyl)propionic acid 
• 24470-14-2 (S)-(+)-2-(4'-methoxyphenyl)propanoic acid 
• 65784-33-0 methyl 2-(4-hydroxyphenyl)propanoate 
• 93397-63-8 2-(4-methoxyphenyl)propan-1-ol 
• 352315-56-1 N-(4-chloro-3-methylisothiazol-5-yl)-2-(4-methoxyphenyl)propionamide 
• 67137-79-5 2-(2,3-dihydro-2-isopropyl-4-oxo-4H-1-benzopyran-6-yl)propionic acid dicyclohexylamine salt 

Relevant articles and documents

Asymmetric Aminations and Kinetic Resolution of Acyclic α-Branched Ynones

An efficient method for asymmetric synthesis of acyclic α-tertiary amine derivatives has been achieved through enantioselective aminations of α-branched ynones with azodicarboxylates enabled by chiral phosphoric acid catalysis. Moreover, kinetic resolution of racemic starting material was realized under these conditions, which gave access to valuable enantioenriched α-substituted ketones. A wide array of α-aryl and alkyl-substitutions, and the substituted alkynyl groups were well compatible with this method, producing both the amination products and the recovered ketones with good to high enantioselectivities.

syn-Selective Michael Reaction of α-Branched Aryl Acetaldehydes with Nitroolefins Promoted by Squaric Amino Acid Derived Bifunctional Br?nsted Bases

Here we describe a direct access to 2,2,3-trisubstituted syn γ-nitroaldehydes by addition of α-branched aryl acetaldehydes to nitroolefins promoted by a cinchona based squaric acid-derived amino acid peptide. Different α-methyl arylacetaldehydes react with β-aromatic and β-alkyl nitroolefins to afford the Michael adducts in high enantioselectivity and syn-selectivity. NMR experiments and DFT calculations predict the reaction to occur through the intermediacy of E-enolate. The interaction between the substrates and the catalyst follows Pápai's model, wherein an intramolecular H-bond interaction in the catalyst between the NH group of one of the tert-leucines and the squaramide oxygen seems to be key for discrimination of the corresponding reaction transition states.

Palladium-Catalyzed Asymmetric Markovnikov Hydroxycarbonylation and Hydroalkoxycarbonylation of Vinyl Arenes: Synthesis of 2-Arylpropanoic Acids

Asymmetric hydroxycarbonylation is one of the most fundamental yet challenging methods for the synthesis of carboxylic acids. Herein, we reported the development of a palladium-catalyzed highly enantioselective Markovnikov hydroxycarbonylation of vinyl arenes with CO and water. A monodentate phosphoramidite ligand L6 plays vital role in the reaction. The reaction tolerates a range of functional groups, and provides a facile and atom-economical approach to an array of 2-arylpropanoic acids including several commonly used non-steroidal anti-inflammatory drugs. The catalytic system has also enabled an asymmetric Markovnikov hydroalkoxycarbonylation of vinyl arenes with alcohols to afford 2-arylpropanates. Mechanistic investigations suggested that the hydropalladation is irreversible and is the regio- and enantiodetermining step, while hydrolysis/alcoholysis is probably the rate-limiting step.

Efficient palladium-catalyzed synthesis of 2-aryl propionic acids

A flexible two-step, one-pot procedure was developed to synthesize 2-aryl propionic acids including the anti-inflammatory drugs naproxen and flurbiprofen. Optimal results were obtained in the presence of the novel ligand neoisopinocampheyldiphenylphosphine (NISPCPP) (9) which enabled the efficient sequential palladium-catalyzed Heck coupling of aryl bromides with ethylene and hydroxycarbonylation of the resulting styrenes to 2-aryl propionic acids. This cascade transformation leads with high regioselectivity to the desired products in good yields and avoids the need for additional purification steps.

A general platinum-catalyzed alkoxycarbonylation of olefins

Hydroxy- and alkoxycarbonylation reactions constitute important industrial processes in homogeneous catalysis. Nowadays, palladium complexes constitute state-of-the-art catalysts for these transformations. Herein, we report the first efficient platinum-catalysed alkoxycarbonylations of olefins including sterically hindered and functionalized ones. This atom-efficient catalytic transformation provides straightforward access to a variety of valuable esters in good to excellent yields and often with high selectivities. In kinetic experiments the activities of Pd- and Pt-based catalysts were compared. Even at low catalyst loading, Pt shows high catalytic activity.

Palladium-Catalyzed Alkoxycarbonylation of sec-Benzylic Ethers

Herein, we report the palladium-catalyzed synthesis of 3-arylpropionate esters starting from secondary benzylic ethers. With this investigation it could be shown that ethers are suitable starting materials in addition to the established carbonylation reactions of olefins, alcohols, or aryl halides.

Iridium-Catalyzed α-Methylation of α-Aryl Esters Using Methanol as the C1 Source

IrCl(cod)2]/dppe-catalyzed α-methylation of aryl esters using methanol as the C1 source was developed. This methylation process is useful in several fields including organic chemistry, biochemistry, and medicinal chemistry. Readily available methanol as methylation reagent was successfully adapted. The reaction processed high atom economy and efficient. By applying the reaction system, the synthesis method of naproxen was provided.

PYRAZOLOTRIAZOLOPYRIMIDINE DERIVATIVES AS A2A RECEPTOR ANTAGONIST

Disclosed herein is a pyrazolotriazolopyrimidine derivative or a stereoisomer thereof, or a pharmaceutically acceptable salt thereof useful as an A2A receptor antagonist, and a pharmaceutical composition comprising the same. Also disclosed herein is a method of treating cancer using the pyrazolotriazolopyrimidine derivative or a stereoisomer thereof, or a pharmaceutically acceptable salt thereof as an A2A receptor antagonist.

Ni-Catalyzed Reductive C-O Bond Arylation of Oxalates Derived from α-Hydroxy Esters with Aryl Halides

A Ni-catalyzed reductive cross-coupling of α-hydroxycarbonyl compounds modified with oxalyl groups and aryl halides has been developed that furnishes α-aryl esters under mild conditions and tolerates a variety of functionalized aryl halides bearing electron-withdrawing and -donating groups. This work highlights C-O bond fragmentation on secondary alkyl carbon centers that generates α-carbonyl radicals.

Stereodivergent coupling of aldehydes and alkynes via synergistic catalysis using Rh and Jacobsen's amine

We report an enantioselective coupling between α-branched aldehydes and alkynes to generate vicinal quaternary and tertiary carbon stereocenters. The choice of Rh and organocatalyst combination allows for access to all possible stereoisomers with high enantio-, diastereo-, and regioselectivity. Our study highlights the power of catalysis to activate two common functional groups and provide access to divergent stereoisomers and constitutional structures.