29540-54-3

Basic information

• Product Name: a-Methyl-b-oxo-benzenepropanoic acid methyl ester
• Synonyms: a-Methyl-b-oxo-benzenepropanoic acid methyl ester;Methyl 2-methyl-3-oxo-3-phenyl-propanoate
• CAS NO: 29540-54-3
• Molecular Formula: C₁₁H₁₂O₃
• Molecular Weight: 192.21118
• Mol File: 29540-54-3.mol
• Article Data: 30

Chemical Properties

• Appearance: /
• Storage Temp.: -20°C Freezer
• Solubility: Dichloromethane
• CAS DataBase Reference: a-Methyl-b-oxo-benzenepropanoic acid methyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: a-Methyl-b-oxo-benzenepropanoic acid methyl ester(29540-54-3)
• EPA Substance Registry System: a-Methyl-b-oxo-benzenepropanoic acid methyl ester(29540-54-3)

Safety Data

• Hazardous Substances Data: 29540-54-3(Hazardous Substances Data)

Usage

Uses

Methyl 2-Methyl-3-oxo-3-phenylpropanoate is an intermediate in the synthesis of Pyrametostrobin (P847010), a novel fungicide. Also, it is derived from 1-Methyl-2-nitrobenzene (N572306), which is a toxic pollutant of the environment because of its large scale use in the production of explosives. It is a useful synthetic intermediate. It shows carcinogenic activity in rats.

Synthesis Reference(s)

The Journal of Organic Chemistry, 48, p. 3833, 1983 DOI: 10.1021/jo00169a053

Upstream product

• 34757-14-7 methyl 2-diazopropanoate 
• 591-50-4 iodobenzene 
• 201230-82-2 carbon monoxide 
• 98-88-4 benzoyl chloride 
• 614-45-9 tert-Butyl peroxybenzoate 
• 614-27-7 methyl 3-oxo-3-phenylpropionate 
• 124-41-4 sodium methylate 
• 93-58-3 benzoic acid methyl ester 
• 554-12-1 propanoic acid methyl ester 
• 100-52-7 benzaldehyde 
• 82111-78-2 methyl 2-benzoylprop-2-enoate 
• 72658-03-8 (Z)-1-methoxy-1-(trimethylsiloxy)propene 
• 134-81-6 benzil 
• 100-47-0 benzonitrile 

Downstream Products

• 93-55-0 1-phenyl-propan-1-one 
• 765271-39-4 methyl 2-fluoro-2-methyl-3-oxo-3-phenylpropanoate 
• 144462-33-9 (R)-methyl 2-fluoro-2-methyl-3-oxo-3-phenyl-propionate 
• 1202873-88-8 C₂₂H₂₃ClN₄O₃ 
• 1202873-76-4 C₂₂H₂₂ClN₃O₄ 
• 7713-78-2 4-methyl-5-phenyl-1,2-dihydro-3H-pyrazol-3-one 
• 29879-49-0 4-methyl-3-phenyl-2H-isoxazol-5-one 
• 23244-37-3 4-methyl-3-phenylisoxazole-5(4H)-one 
• 1361978-88-2 methyl 2-azido-2-methyl-3-oxo-3-phenylpropanoate 
• 1390681-59-0 2,2,2-tris(4,5,6,7,8,9-hexahydro-1H-cycloocta[d][1,2,3]triazol-1-yl)-1-phenylethanone 
• 94199-26-5 (2S,3R)-methyl 3-hydroxy-2-methyl-3-phenylpropionate 

Relevant articles and documents

Palladium Catalyzed Ring Expansion Reaction of Isoxazolones with Isocyanides: Synthesis of 1,3-Oxazin-6-One Derivatives

A palladium catalyzed ring expansion reaction of isoxazolones with isocyanides was disclosed. In the reaction, a cascade process involving ring-opening/cyclization was suggested. The reaction features high atomic economy due to no elimination of CO2 occurred. Moreover, products obtained demonstrate aggregation-induced emission properties with relatively high solid-state emission efficiencies. (Figure presented.).

Radical Chlorodifluoromethylation: Providing a Motif for (Hetero)arene Diversification

A method for the radical chlorodifluoromethylation of (hetero)arenes using chlorodifluoroacetic anhydride is reported. This operationally simple protocol proceeds under mild photochemical conditions with high functional group compatibility and complements the large body of literature for the trifluoromethylation of (hetero)arenes. Introduction of the chlorodifluoromethyl motif enables rapid diversification to a wide array of aromatic scaffolds. This work showcases the chlorodifluoromethyl group as an attractive entryway to otherwise synthetically challenging electron-rich difluoromethyl(hetero)arenes. Furthermore, facile conversion of the CF2Cl moiety into the corresponding aryl esters, gem-difluoroenones, and β-keto-esters is demonstrated.

A General and Robust Method for the Preparation of (E)- and (Z)-Stereodefined Fully Substituted Enol Tosylates: Promising Cross-Coupling Partners

A robust method for preparing (E)- and (Z)-stereodefined fully substituted enol tosylates is described. α-Substituted β-keto esters undergo (E)-selective enol tosylations using TsCl-Me2N(CH2)6NMe2 as the reagent (method A, 13 examples; 63-96%) and (Z)-selective enol tosylations using TsCl-TMEDA-LiCl as the reagent (method B, 13 examples; 62-99%). A plausible mechanism for the (E)- and (Z)-enol tosylation selectivity is proposed. A 1H NMR monitoring experiment revealed that TsCl coupled with TMEDA formed a simple N-sulfonylammonium intermediate.