733-07-3

Basic information

• Product Name: DIMESITYLMETHANE
• Synonyms: DIMESITYLMETHANE;2-(Mesitylmethyl)-1,3,5-trimethylbenzene;Benzene, 1,1'-methylenebis[2,4,6-trimethyl-;Bis(2,4,6-trimethylphenyl)methane~2,2-Methylenedimesitylene;2,2'-methylenedimesitylene;bis(2,4,6-trimethylphenyl)methane;Dimesitylmethane, 98+%;2,2'-Methylenebis(1,3,5-trimethylbenzene)
• CAS NO: 733-07-3
• Molecular Formula: C₁₉H₂₄
• Molecular Weight: 252.39
• EINECS: 211-991-6
• Mol File: 733-07-3.mol

Chemical Properties

• Melting Point: 132-135 °C(lit.)
• Boiling Point: 370.7°C at 760 mmHg
• Flash Point: 192.8°C
• Appearance: /
• Density: 0.947g/cm³
• Vapor Pressure: 2.31E-05mmHg at 25°C
• Refractive Index: 1.547
• BRN: 2053472
• CAS DataBase Reference: DIMESITYLMETHANE(CAS DataBase Reference)
• NIST Chemistry Reference: DIMESITYLMETHANE(733-07-3)
• EPA Substance Registry System: DIMESITYLMETHANE(733-07-3)

Safety Data

• Safety Statements: 22-24/25
• WGK Germany: 3
• Hazardous Substances Data: 733-07-3(Hazardous Substances Data)

Usage

Uses

Used in Chemical Research:
Dimesitylmethane is employed as a laboratory reagent, particularly for its highly sterically hindered methylene group. This unique structural feature makes it a valuable compound for studying steric effects in chemical reactions and syntheses.
Used in Metal Complexes:
Dimesitylmethane is used as a strong ligand in the formation of metal complexes. Its ability to form stable complexes with various metals is beneficial for applications in catalysis, materials science, and the development of new compounds with tailored properties.
Used in Organic Synthesis:
Due to its resonance stabilization and resistance to oxidation, dimesitylmethane can be utilized as an intermediate or building block in the synthesis of more complex organic molecules, particularly in the development of novel aromatic hydrocarbons and related compounds.

InChI:InChI=1/C19H24/c1-12-7-14(3)18(15(4)8-12)11-19-16(5)9-13(2)10-17(19)6/h7-10H,11H2,1-6H3

Upstream product

• 64-19-7 acetic acid 
• 108-67-8 1,3,5-trimethyl-benzene 
• 107-30-2 chloromethyl methyl ether 
• 7446-70-0 aluminium trichloride 
• 625-56-9 Chloromethyl acetate 
• 628-51-3 diacetoxymethane 
• 7664-93-9 sulfuric acid 
• 74-95-3 1,1-dibromomethane 
• 4382-76-7 methoxymethyl acetate 
• 21127-91-3 Bis-(2,4,6-trimethyl-phenyl)-methanol 
• 75-05-8 acetonitrile 
• 5980-97-2 mesitylboronic acid 
• 80-48-8 methyl p-toluene sulfonate 
• 38542-71-1 N-methylpyridinium p-toluenesulfonate 

Downstream Products

• 70335-42-1 bis-(3-bromo-2,4,6-trimethyl-phenyl)methane 
• 1364188-48-6 N-(2',4',6'-trimethyl-3'-(2,4,6-trimethylbenzyl)biphenyl-4-yl)-N-(2,4,6-trimethyl-3-(2,4,6-trimethylbenzyl)phenyl)acetamide 
• 1370257-08-1 5,5'-methylenebis-(2,4,6-trimethylisophthalic acid) 
• 1370257-10-5 C₂₃H₃₂O₄ 
• 1370257-09-2 C₃₁H₄₀O₈ 
• 959935-47-8 3,3',5,5'-tetrakis(bromomethyl)-2,2',4,4',6,6'-hexamethyldiphenylmethane 
• 913724-95-5 bis(3-((diphenylphosphino)methyl)-2,4,6-trimethylphenyl)methane 
• 134284-57-4 dimesitylmethane-3,3'-dicarbaldehyde 
• 487-68-3 mesytaldehyde 
• 105041-52-9 2,4,6-trimethyl-3-(chloromethyl)benzaldehyde 
• 134284-58-5 3-chloromethyl-2,4,6-trimethylbenzylidene dichloride 
• 913724-94-4 3,3'-bis(bromomethyl)-2,2',4,4',6,6'-hexamethyldiphenylmethane 

Relevant articles and documents

Development of Versatile Sulfone Electrophiles for Suzuki-Miyaura Cross-Coupling Reactions

The development of fluorinated sulfone derivatives as versatile electrophiles for Suzuki-Miyaura cross-coupling reactions is described. Introducing electron-withdrawing groups on the aryl ring of the sulfone facilitates the Pd-catalyzed activation of C-SO2 bonds. Cross-coupling reactions with fluorinated sulfone electrophiles are reported, leading to a variety of multiply arylated products in good yields. The reactivity of this unusual electrophile is benchmarked versus common electrophiles and its use in iterative cross-couplings for concise synthesis of biologically active molecules is described.

Functional Ionic Liquids as Efficient and Recyclable Catalysts for the Methylation of Formaldehyde with Aromatics

Abstract: Methylation of formaldehyde with various aromatics under functional ionic liquids catalysis has been developed. Among the ionic liquids investigated, triphenyl-(4-sulfobutyl)-phosphonium triflate ([TTPBs][CF3SO3]) showed high activity and afforded excellent yields of diarylmethane derivatives. A mechanism for the catalytic performance of [TTPBs][CF3SO3] is proposed. Besides, the catalyst can simply be separated from the reaction mixture by centrifugation and be recycled ten times without noticeable loss of activity. Graphical Abstract: Diarylmethane derivatives were successfully synthesized from the methylation of formaldehyde with aromatics using efficient and recyclable functional ionic liquids as catalysts, excellent yields and selectivities were obtained under solvent free conditions. The catalyst was reused at least ten consecutive recycles without noticeable loss in its catalytic activity. Meanwhile, the usability of catalyst was explored.[Figure not available: see fulltext.]

A tubular europium-organic framework exhibiting selective sensing of Fe3+ and Al3+ over mixed metal ions

A luminescent europium-organic framework with tubular channels based on the H4BTMIPA ligand (H4BTMIPA = 5,5′-methylenebis(2,4, 6-trimethylisophthalic acid)) was assembled and characterized. The [H 2N(CH3)2]+ ions as counterions are located in the channels. The cation exchange between [H2N(CH 3)2]+ and metal ions resulted in complex 1 that can selectively sense Fe3+ and Al3+ ions through fluorescence quenching and enhancement, respectively.

Phase transfer catalyst supported, room-temperature biphasic synthesis: A facile approach to the synthesis of coordination polymers

A facile approach, named phase transfer catalyst supported, room temperature biphasic synthesis, has been developed to synthesize a new type of coordination polymers. Compared to the traditional biphasic solvothermal synthesis that was run at high temperature (100-200 °C), the new approach introduced here can be operated under a mild condition (room temperature) with the support of phase transfer catalyst. With the application of this new approach, two copper coordination complexes with 1D metal-organic nanotube and 1D coordination polymer containing large water clusters have been successfully synthesized and characterized. Furthermore, the synthetic approach presented here can be extended to synthesize other coordination polymers, including porous lanthanide-organic frameworks.

Sulfonylation of aromatic compounds with methyl p-toluenesulfonate as a sulfonylating precursor

We have developed Friedel-Crafts (FC) sulfonylation of aromatic compounds with methyl p-toluenesulfonate as a sulfonylating precursor. In this procedure, methyl p-toluenesulfonate was treated and activated with pyridine to produce N-methylpyridinium p-toluenesulfonate as a sulfonylation reagent. Reactivity of this salt for the sulfonylation of mesitylene was investigated in the presence of three different promoters, such as triflic anhydride, dimethylsulfide ditriflate, and triphenylphosphine ditriflate (TPPD). All of the promoters show chemoselectivity and among them, TPPD presents a chemoselectivity in FC sulfonylation. Iranian Chemical Society 2012.

o-Benzenedisulfonimide as a reusable Bronsted acid catalyst for Ritter-type reactions

Reactions between various benzyl alcohols or tert-butyl alcohol and nitriles were carried out in the presence of catalytic amounts (usually 10-20 mol-%) of o-benzenedisulfonimide as a Bronsted acid catalyst; the reaction conditions were mild and the yields of amides were good. The catalyst was easily recovered and purified, ready to be used in further reactions, with economic and ecological advantages. Wiley-VCH Verlag GmbH & Co. KGaA, 2009.

Pentafluorophenylation of aromatic compounds with 4,5,6,7,8-pentafluoro-6- nitro-1-oxaspiro[2.5]octa-4,7-diene

4,5,6,7,8-Pentafluoro-6-nitro-1-oxaspiro[2.5]octa-4,7-diene reacts with arenes in the presence of AlCl3 to give pentafluorobiphenyls.

Non-coplanar aromatic carboxylic acids: Unusual conformation-dependent self-assembly and pseudopolymorphism of di(3-carboxymesityl)methane

The dicarboxylic acids 3 and 4, i.e., di(3-carboxy-2,4,6-trimethylphenyl)methane and di(3-carboxyphenyl)methane, are created by a methylene tethering of mesitoic acid and benzoic acid, respectively. These diacids may explore two low energy conformations, viz., syn and anti. Whereas the syn-diacid 3 is found to undergo self-assembly in the solid state via a very rare tetrameric motif, the anti-diacid 3 is found to exhibit pseudopolymorphism with guest molecules such as DMSO and PhOH-H2O. The unusual patterns of assembly and the occurrence of pseudopolymorphism for the syn and anti conformers, respectively, appear to emanate from an unique structural feature that emerges as a consequence of tethering. It appears that the molecules that contain strongly interacting functional groups in non-coplanar aryl rings will suffer from packing problems, which manifests itself in a new mode of packing and the phenomenon of pseudopolymorphism.

An efficient synthesis of diarylmethanes via InCl3*4H2O-catalyzed dehydration of electron-rich arenes with trioxane

A facile, efficient and environmentally benign procedure for the synthesis of diarylmethanes via the reaction of arenes with trioxane catalyzed by InCl3*4H2O was developed. The reactions of aromatic compounds bearing electron-donating group proceeded smoothly affording the corresponding diarylmethanes in good to excellent yields.

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.