25305-41-3

Basic information

• Product Name: Methanone, 1,3,5-benzenetriyltris[(4-methylphenyl)-
• CAS NO: 25305-41-3
• Molecular Formula: C30H24O3
• Molecular Weight: 432.519
• Mol File: 25305-41-3.mol

Chemical Properties

• CAS DataBase Reference: Methanone, 1,3,5-benzenetriyltris[(4-methylphenyl)-(CAS DataBase Reference)
• NIST Chemistry Reference: Methanone, 1,3,5-benzenetriyltris[(4-methylphenyl)-(25305-41-3)
• EPA Substance Registry System: Methanone, 1,3,5-benzenetriyltris[(4-methylphenyl)-(25305-41-3)

Safety Data

• Hazardous Substances Data: 25305-41-3(Hazardous Substances Data)

Upstream product

• 14377-18-5 1-(4-methylphenyl)prop-2-yn-1-one 
• 110-89-4 piperidine 
• 64-17-5 ethanol 
• 107-91-5 cyanoacetic acid amide 
• 14377-02-7 3-oxo-3-p-tolyl-propionaldehyde 
• 141-52-6 sodium ethanolate 
• 122-00-9 para-methylacetophenone 
• 41125-10-4 benzoylacetaldehyde sodium salt 
• 18103-98-5 3-dimethylamino-1-(4-methyl-phenyl)-2-propen-1-one 
• 18103-98-5 (E)-3-(dimethylamino)-1-p-tolylprop-2-en-1-one 
• 4422-95-1 1,3,5-benzene tris(carbonyl chloride) 
• 108-88-3 toluene 

Downstream Products

• 437981-36-7 [3,5-bis-(4-bromomethyl-benzoyl)-phenyl]-(4-bromomethyl-phenyl)-methanone 

Relevant articles and documents

Facile synthesis of 1,3,5-triaroylbenzenes by direct cyclotrimerization of ketone enolates

Based on the improvement of the synthesis of 1,3,5-triaroylbenzenes, a convenient acid catalytic strategy was carried out and a series of 1,3,5-triaroylbenzenes were synthesized. The reaction temperature effect was investigated, and a mechanism of the cyclotrimerization has been proposed. Copyright Taylor & Francis Group, LLC.

Cyclotrimerization of Enaminones: An Efficient Method for the Synthesis of 1,3,5-Triaroylbenzenes

An efficient method for the synthesis of 1,3,5-triaroylbenzenes 2a-f by cyclotrimerization of enaminones 1a-f in acetic acid/pyridine (4:1) is illustrated. The structures of the products have been delineated by spectroscopic methods.

One-pot synthesis of 1,3,5-tribenzoylbenzenes by three consecutive michael addition reactions of 1-phenyl-2-propyn-1-ones in pressurized hot water in the absence of added catalysts

Cyclotrimerization of 1-phenyl-2-propyn-1-one in pressurized hot water gave 1,3,5-tribenzoylbenzene in one pot in 65% yield after 7min at 200°C, or in 74% yield after 60min at 150°C. The reaction did not take place in the absence of water, and added base promoted the reaction at 250°C, suggesting a mechanism of three-consecutive Michael addition reactions. The reaction rates increased with temperature, but the yield of 1,3,5-tribenzoylbenzene decreased at the expense of formation of acetophenone as a side product at higher temperatures. p-Methyl and p-chloro-substituents on the phenyl ring retarded and enhanced the reaction, respectively. A mechanism involving the enol of benzoylacetaldehyde at a branching point of the pathway leading to 1,3,5-tribenzoylbenzene and acetophenone was suggested.

A new organocatalytic process of cyclotrimerization of acetylenic ketones mediated by 2,4-pentanedione

A new organocatalytic process of cyclotrimerization of the aliphatic and aromatic acetylenic ketones was developed. The reaction catalyzed by DMAP in the presence of 2,4-pentanedione gave 1,3,5-trisubstituted benzenes in almost quantitative yields under very mild conditions. 2,4-Pentanedione was used as a co-catalyst to promote the reaction efficiently, particularly for aliphatic acetylenic ketones. Georg Thieme Verlag Stuttgart.

Preparation method of carbonyl functionalized type aromatic carboxylic acid

The invention discloses a preparation method of carbonyl functionalized type aromatic carboxylic acid. The preparation method comprises the following steps of enabling aromatic acid halide and methylbenzene to generate Friedel-Crafts reaction to produce a

Metal-free synthesis of 1,3,5-trisubstituted benzenes by the cyclotrimerization of enaminones or alkynes in water

The cyclotrimerization reactions of enaminones and electron deficient terminal alkynes have been efficiently performed in water in the presence of only a small amount of lactic acid. The reactions led to the green synthesis of a variety of 1,3,5-triacylbenzenes without using any metal as catalyst. Brief investigation on different elaboration of the triacylbenzene product demonstrated the versatile synthetic application of these 1,3,5-triacylbenzenes. This journal is the Partner Organisations 2014.

Mechanistic and exploratory investigations into the synthesis of 1,3,5-triaroylbenzenes from 1-aryl-2-propyn-1-ones and 1,3,5-triacetylbenzene from 4-methoxy-3-buten-2-one by cyclotrimerization in hot water in the absence of added acid or base

Neat 1-phenyl- and 1-(p-tolyl)-2-propyn-1-ones (1 and 1′, respectively) were heated in water without any additive at 150 °C for 2 h to give 1,3,5-tribenzoyl- and 1,3,5-tri-(p-toluoyl)benzenes (2 and 2′, respectively) in 74 and 52% yields, respectively. The crossed reactions of 1 with the enolate of p-toluoylacetaldehyde (3′) and 1′ with the enolate of benzoylacetaldehyde (3) were carried out to give unsymmetrically substituted 1-toluoyl-3,5-dibenzoylbenzene (Ph2Tol) and 1,3-ditoluoyl-5-benzoylbenzene (PhTol2), respectively, corroborating the previously proposed reaction mechanism in which 3 and 3′ that are formed by rate-determining nucleophilic attack of HO- on 1 and 1′ or its conjugate acids formed by subsequent protonation would serve as a common intermediate for the formation of 2, 2′ and the acetophenone derivatives as byproducts. When 4-methoxy-3-buten-2-one (4) was heated in hot pure water without any additive at 150 °C for 30 min, 1,3,5-triacetylbenzene (5) was obtained in an isolated yield of 77% just by removing water by filtering the crystalline product from the cooled reaction mixture. The reaction did not take place in the absence of water. Slow decompositions of 5 in water set in at the temperature of 300 °C for 30 min.

Enaminones in heterocyclic synthesis: A new regioselective synthesis of 2,3,6-trisubstituted pyridines, 6-substituted-3-aroylpyridines and 1,3,5-triaroylbenzenes

1-Substituted-3-dimethylaminopropenones 1a-d reacted with acetylacetone and with ethyl acetoacetate to yield regioselectively 2,3,6-trisubstituted pyridines. Refluxing 1a-d in acetic acid/ammonium acetate resulted in the formation of 6-substituted-3-aroylpyridines, whereas refluxing in acetic acid alone afforded 1,3,5-triaroylbenzene.

Synthesis of bicyclic cyclophanes with chiral cages by sixfold coupling

Coupling of (S)-binol with various tribromides afforded bicyclic cyclophanes by sixfold coupling. Coupling of tricarbonyl tribromide with binol gave a novel chiral cyclophane with six co-ordination sites for complexation.