77959-48-9

Basic information

• Product Name: methyl 4-(1-methoxy-1-oxopropan-2-yl)benzoate
• Synonyms: Benzeneacetic acid, 4-(methoxycarbonyl)-alpha-methyl-, methyl ester
• CAS NO: 77959-48-9
• Molecular Formula: C₁₂H₁₄O₄
• Molecular Weight: 222.2372
• Mol File: 77959-48-9.mol
• Article Data: 15

Chemical Properties

• Boiling Point: 303°C at 760 mmHg
• Flash Point: 145.7°C
• Density: 1.125g/cm³
• Vapor Pressure: 0.000958mmHg at 25°C
• Refractive Index: 1.505
• CAS DataBase Reference: methyl 4-(1-methoxy-1-oxopropan-2-yl)benzoate(CAS DataBase Reference)
• NIST Chemistry Reference: methyl 4-(1-methoxy-1-oxopropan-2-yl)benzoate(77959-48-9)
• EPA Substance Registry System: methyl 4-(1-methoxy-1-oxopropan-2-yl)benzoate(77959-48-9)

Safety Data

• Hazardous Substances Data: 77959-48-9(Hazardous Substances Data)

Upstream product

• 17639-93-9 2-chloro-propionic acid methyl ester 
• 1126-46-1 Methyl 4-chlorobenzoate 
• 619-42-1 4-methoxycarbonylphenyl bromide 
• 938-94-3 (R,S)-2-(4'-methylphenyl) propionic acid 
• 67-56-1 methanol 
• 201230-82-2 carbon monoxide 
• 1076-96-6 methyl 4-vinylbenzoate 
• 124-38-9 carbon dioxide 
• 136333-97-6 methyl 4-(2-bromoethyl)benzoate 
• 619-44-3 methyl 4-iodobenzoate 
• 4648-54-8 trimethylsilylazide 
• 35733-58-5 tetra(n-butyl)ammonium formate 
• 1075-49-6 4-ethenylbenzoic acid 
• 554-12-1 propanoic acid methyl ester 

Downstream Products

• 88392-94-3 4-amino-4-deoxy-10-methyl-10-carbomethoxy-8,10-dideazapteroate 
• 272779-21-2 4-[2-(2,4-diamino-pteridin-6-yl)-1-methoxycarbonyl-1-methyl-ethyl]-benzoic acid methyl ester 
• 80576-76-7 4-amino-4-deoxy-10-methyl-10-deazapteroic acid 
• 272779-22-3 4-[1-carboxy-2-(2,4-diamino-pteridin-6-yl)-1-methyl-ethyl]-benzoic acid 
• 88392-98-7 4-amino-4-deoxy-10-methyl-8,10-dideazapteroic acid 
• 88393-04-8 (S)-2-{4-[2-(2,4-Diamino-pyrido[3,2-d]pyrimidin-6-yl)-1-methyl-ethyl]-benzoylamino}-pentanedioic acid 
• 88393-01-5 (S)-2-{4-[2-(2,4-Diamino-pyrido[3,2-d]pyrimidin-6-yl)-1-methyl-ethyl]-benzoylamino}-pentanedioic acid diethyl ester 
• 67381-50-4 (±)-4-(1-carboxyethyl)benzoic acid 

Relevant articles and documents

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.

A Metallaphotoredox Strategy for the Cross-Electrophile Coupling of α-Chloro Carbonyls with Aryl Halides

Here, we demonstrate that a metallaphotoredox-catalyzed cross-electrophile coupling mechanism provides a unified method for the α-arylation of diverse activated alkyl chlorides, including α-chloroketones, α-chloroesters, α-chloroamides, α-chlorocarboxylic acids, and benzylic chlorides. This strategy, which is effective for a wide variety of aryl bromide coupling partners, is predicated upon a halogen atom abstraction/nickel radical-capture mechanism that is generically successful across an extensive range of carbonyl substrates. The construction and use of arylacetic acid products have further enabled two-step protocols for the delivery of valuable building blocks for medicinal chemistry, such as aryldifluoromethyl and diarylmethane motifs.

Metallic reductant-free synthesis of α-substituted propionic acid derivatives through hydrocarboxylation of alkenes with a formate salt

A PGeP-pincer palladium-catalyzed hydrocarboxylation of styrenes to obtain pharmaceutically important α-arylpropionic acid derivatives was achieved using a formate salt as both a reductant and a CO2 source. The reaction was also applicable to vinylsulfone and acrylates. Isotope labeling experiments demonstrated that a CO2-recycling mechanism is operative through generation and reaction of a benzylpalladium complex as a carbon nucleophile. This protocol has realized a mild and atom economical CO2-fixation reaction without the necessity of using strong metallic reductants.