136942-13-7

Basic information

• Product Name: methyl 1-phenyl-3-(mtolyl)propane-1,3-dione
• Synonyms: methyl 1-phenyl-3-(mtolyl)propane-1,3-dione
• CAS NO: 136942-13-7
• Molecular Weight: 238.286
• Mol File: 136942-13-7.mol
• Article Data: 9

Chemical Properties

• CAS DataBase Reference: methyl 1-phenyl-3-(mtolyl)propane-1,3-dione(CAS DataBase Reference)
• NIST Chemistry Reference: methyl 1-phenyl-3-(mtolyl)propane-1,3-dione(136942-13-7)
• EPA Substance Registry System: methyl 1-phenyl-3-(mtolyl)propane-1,3-dione(136942-13-7)

Safety Data

• Hazardous Substances Data: 136942-13-7(Hazardous Substances Data)

Upstream product

• 38404-42-1 methyl 3,4-dimethylbenzoate 
• 98-86-2 acetophenone 
• 98-88-4 benzoyl chloride 
• 585-74-0 3-Methylacetophenone 
• 53692-58-3 1-(3-methylphenyl)-3-phenylpropynone 
• 932-90-1 Benzaldoxime 
• 14674-99-8 1-phenyl-3-(3-methylphenyl)prop-2-yn-1-one 
• 136125-68-3 methyl 3-methylphenylglyoxylate 
• 70-11-1 α-bromoacetophenone 
• 93-89-0 benzoic acid ethyl ester 

Downstream Products

• 40103-79-5 1-(3-methylphenyl)-2-phenyl-1,2-ethanedione 

Relevant articles and documents

Rhodium-Catalyzed Aerobic Decomposition of 1,3-Diaryl-2-diazo-1,3-diketones: Mechanistic Investigation and Application to the Synthesis of Benzils

The conversion of 1,3-diaryl-2-diazo-1,3-diketones to 1,2-daryl-1,2-diketones (benzils) is reported based on a rhodium(II)-catalyzed aerobic decomposition process. The reaction occurs at ambient temperatures and can be catalyzed by a few dirhodium carboxylates (5 mol %) under a balloon pressure of oxygen. Moreover, an oxygen atom from the O2 reagent is shown to be incorporated into the product, and this is accompanied by the extrusion of a carbonyl unit from the starting materials. Mechanistically, it is proposed that the decomposition may proceed via the interaction of a ketene intermediate resulting from a Wolff rearrangement of the carbenoid, with a rhodium peroxide or peroxy radical species generated upon the activation of molecular oxygen. The proposed mechanism has been supported by the results from a set of controlled experiments. By using this newly developed strategy, a large array of benzil derivatives as well as 9,10-phenanthrenequinone were synthesized from the corresponding diazo substrates in varying yields. On the other hand, the method did not allow the generation of benzocyclobutene-1,2-dione from 2-diazo-1,3-indandione because of the difficulty of inducing the initial rearrangement.

An effective preparation of both 1,3-diketones and nitriles from alkynones with oximes as hydroxide sources

An effective phosphine-catalyzed protocol has been established for the syntheses of 1,3-diketones and nitriles from alkynones with oximes as hydroxide surrogates. This method features the use of a phosphine catalyst, compatibility with various functional groups and ambient temperature, which makes this approach very practical. A plausible mechanism was proposed.

Asymmetric transfer hydrogenation of unsymmetrical benzils

In this paper, the asymmetric transfer hydrogenation of unsymmetrical benzils with m, p-substituents was conducted with a substrate/catalyst molar ratio of 100 at 40°C for 24 h to produce (S,S)-hydrobenzoins in good yields (76.2% to 97.1%) with high diastereomeric (syn/anti = 10.8 to 29.7/1) and enantiomeric purities (86.1%ee syn to 98.9%ee syn). Unfortunately, the unsymmetrical benzils with the o-substituents such as electron-donating (R = CH3, OCH3) and electron-withdrawing groups (R = F, Cl, CF3) resulted in poor yields (0% to 31.2%), even at 40°C for 72 h. These products had inefficient diastereoselectivities (syn/anti = 1.5 to 5.0/1) caused by steric effects. Furthermore, the results of a dynamic-kinetic study were used to propose a plausible reaction pathway of unsymmetrical benzil using 3-methoxy-1,2-diphenyl ethanedione as an example.