144446-67-3

Basic information

• Product Name: Benzene, 1,3,5-trimethyl-2,4-bis(phenylmethyl)-
• CAS NO: 144446-67-3
• Molecular Formula: C23H24
• Molecular Weight: 300.444
• Mol File: 144446-67-3.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: Benzene, 1,3,5-trimethyl-2,4-bis(phenylmethyl)-(CAS DataBase Reference)
• NIST Chemistry Reference: Benzene, 1,3,5-trimethyl-2,4-bis(phenylmethyl)-(144446-67-3)
• EPA Substance Registry System: Benzene, 1,3,5-trimethyl-2,4-bis(phenylmethyl)-(144446-67-3)

Safety Data

• Hazardous Substances Data: 144446-67-3(Hazardous Substances Data)

Upstream product

• 100-51-6 benzyl alcohol 
• 108-67-8 1,3,5-trimethyl-benzene 
• 100-44-7 benzyl chloride 
• 4453-79-6 2-benzyl-1,3,5-trimethylbenzene 
• 98-88-4 benzoyl chloride 
• 497949-70-9 benzyl N-phenyl-sulfamoylcarbamate 

Relevant articles and documents

Green, Mild, and Efficient Friedel–Crafts Benzylation of Scarcely Reactive Arenes and Heteroarenes under On-Water Conditions

Metal-free Friedel–Crafts benzylation (FCB) of scarcely reactive arenes and heteroarenes was performed under on-water conditions by an environmentally sustainable procedure. The catalytic strategy exploits the hydrophobicity of the resorcinarene macrocycle 1 a. The proposed mechanism is based on the activation of benzyl chloride by H-bonding interactions with catalyst 1 a. In fact, under on-water conditions the hydrophobic amplification of the strength of the H-bonding interactions between the OH groups of the resorcinarene catalyst and the chlorine atom of benzyl chloride leads to polarization of the C?Cl bond, which consequently promotes electrophilic attack of the π nucleophile. Thus, many arenes and heteroarenes were efficiently benzylated under mild on-water conditions by using resorcinarene 1 a as catalyst. The FCB of benzene is industrially relevant for the synthesis of diphenylmethane, and hence the on-water procedure was extended to the gram-scale synthesis of diphenylmethane, starting from benzene and benzyl chloride in the presence of resorcinarene catalyst 1 a.

Effect of mesoporosity on selective benzylation of aromatics with benzyl alcohol over mesoporous ZSM-5

The effect of mesoporosity on product distribution in benzylation of aromatics such as benzene, toluene, anisole and mesitylene with benzyl alcohol was investigated over various ZSM-5 catalysts with different degree of mesoporosity, which were prepared by microwave-induced assembly via ionic interaction between sulfonic acid-functionalized or non-functionalized ZSM-5 nanozeolites and counter cationic surfactant, and hydrothermal synthesis with or without sulfonic acid functionalization and surfactant. The product distribution of the aromatic benzylation was found to vary with the different mesoporosity. The selectivity of desired monobenzylated aromatic was increased from 19.8% to 75.5% with increasing mesopore volume from 0.11 to 0.75 cm 3/g. Meso ZSM-5 (SO3H-CTAB)-MW with the highest external acid sites and mesopore volume showed better conversion as well as much higher selectivity of desired bulky monobenzylated aromatics than those of other catalysts, whereas microporous ZSM-5 mainly showed dibenzyl ether as major product due to diffusion limitation of bulky product.

Uncatalyzed Friedel-Crafts alkylation of aromatic compounds through reactive benzyl cations generated from N-sulfamoylcarbamates

(Matrix presented) A new method for the generation of highly reactive benzyl cations by thermal decomposition of aryl-benzyl-sulfamoylcarbamates, obtained in a one-pot reaction from chlorosulfonyl isocyanate, is described. The generated cations alkylate aromatic compounds efficiently in the absence of catalysts.