5184-64-5

Basic information

• Product Name: 1,3,5-trimethyl-2-[(4-methylphenyl)sulfonyl]benzene
• Synonyms: mesityl (4-methylphenyl) sulfone
• CAS NO: 5184-64-5
• Molecular Formula: C₁₆H₁₈O₂S
• Molecular Weight: 274.3779
• Mol File: 5184-64-5.mol

Chemical Properties

• Boiling Point: 426.7°C at 760 mmHg
• Flash Point: 250°C
• Density: 1.129g/cm³
• Vapor Pressure: 4.33E-07mmHg at 25°C
• Refractive Index: 1.562
• CAS DataBase Reference: 1,3,5-trimethyl-2-[(4-methylphenyl)sulfonyl]benzene(CAS DataBase Reference)
• NIST Chemistry Reference: 1,3,5-trimethyl-2-[(4-methylphenyl)sulfonyl]benzene(5184-64-5)
• EPA Substance Registry System: 1,3,5-trimethyl-2-[(4-methylphenyl)sulfonyl]benzene(5184-64-5)

Safety Data

• Hazardous Substances Data: 5184-64-5(Hazardous Substances Data)

Usage

Physical state

Crystalline solid

Functional groups

Three methyl groups, one sulfonyl group

Structure

Benzene derivative

Applications

a. Building block in organic synthesis
b. Production of pharmaceuticals
c. Production of agrochemicals
d. Production of dyes
e. Chemical intermediate in synthesis of aromatic compounds
f. Precursor for other organic compounds

Importance

Wide range of applications in the chemical industry, development of new materials and drugs

Upstream product

• 98-59-9 p-toluenesulfonyl chloride 
• 108-67-8 1,3,5-trimethyl-benzene 
• 773-64-8 2-mesitylenesulphonyl chloride 
• 108-88-3 toluene 
• 6192-52-5 p-toluenesulfonic acid monohydrate 
• 104-15-4 toluene-4-sulfonic acid 
• 657-84-1 sodium tosylate 
• 4083-64-1 Tosyl isocyanate 
• 1950-69-2 toluene-p-sulfonyl bromide 
• 13505-32-3 N-tosyl-(S)-phenylalanine 
• 4124-41-8 p-toluenesulfonylanhydride 
• 70-55-3 toluene-4-sulfonamide 
• 19158-51-1 P-toluenesulfonyl cyanide 
• 38542-71-1 N-methylpyridinium p-toluenesulfonate 

Downstream Products

• 13189-22-5 2,4-dimethyl-6-(4-methyl-benzyl)-benzenesulfinic acid 

Relevant articles and documents

Metal-free sulfonylation of arenes with: N -fluorobenzenesulfonimide via cleavage of S-N bonds: expeditious synthesis of diarylsulfones

A novel metal-free sulfonylation of arenes with N-fluorobenzenesulfonimide (NFSI) toward the synthesis of diarylsulfones has been developed. The reaction represents a rare example of sulfonylation reaction using NFSI as an efficient sulfonyl donor and the first example of acid-mediated sulfonylation of unactivated arenes with NFSI via selective cleavage of S-N bonds. This protocol provides a concise approach for the construction of pharmaceutically and biologically important diarylsulfones. Applications in the functionalization of natural products (e.g., β-estradiol) and in the synthesis of a key intermediate to an inhibitor of farnesyl-protein transferase, as well as in the gram-scale synthesis of the EPAC2 antagonist, are demonstrated. This journal is

TosMIC and its derivatives as versatile sulfonylating agents for the synthesis of p-toluenesulfonylarenes from aryl halides and arylboronic acids

An efficient copper(II) catalyzed sulfonyation of aryl halides has been achieved using TosMIC (p-toluenesulfonylmethyl isocyanide) as a sulfonylating agent. This newly developed sulfonylation approach provides an easy access for the synthesis of diaryl sulfones from aryl bromides, iodides and boronic acids with TosMIC under neutral conditions. This method is useful for the sulfonylation of aryl boronic acids under similar conditions. This is the first report on the sulfonylation of aryl bromides, iodides and boronic acids using TosMIC.

Selective Synthesis of ortho-Substituted Diarylsulfones by Using NHC-Au Catalysts under Mild Conditions

A single-step gold(I)-catalyzed chemoselective protocol to access ortho-substituted diarylsulfones has been established. Acenaphthoimidazolylidene gold complexes are effective catalysts for the arylsulfonylation of boronic acids by potassium metabisulfite (K2S2O5) and diaryliodonium salts to access (poly-)ortho-substituted diarylsulfones even in gram scale. Unlike the transition metal-catalyzed two-component coupling systems, the sterically hindered aryl groups in diaryliodonium salts are preferentially transferred over less bulky ones to form synthetically difficult targets, including those of pharmaceutical importance.

Copper-mediated sulfonylation of aryl iodides and bromides with arylsulfonyl hydrazides in PEG-400

Sulfonylation using stable and readily available arylsulfonyl hydrazides and aryl iodides or bromides mediated by cupric acetate has been achieved. Using polyethylene glycol (PEG-400) as an eco-friendly medium, the coupling reaction could afford a series of unsymmetrical diaryl sulfones in moderate to good yields without the presence of additional ligands and base.

MODULATORS OF EXCHANGE PROTEINS DIRECTLY ACTIVATED BY CAMP (EPACS)

Embodiments of the invention are directed to compounds that inhibit an activity of EP AC proteins and methods of using the same. The inventors have developed a sensitive and robust high throughput screening (HTS) assay for the purpose of identifying EPAC specific inhibitors (Tsalkova et al. (2012) PLOS ONE 7(1 ):e30441).

A Metal-Free and Microwave-Assisted Efficient Synthesis of Diaryl Sulfones

An efficient and general protocol for the synthesis of diaryl sulfones via the metal-free coupling of readily available diaryliodonium salts and arenesulfinates in PEG-400 under microwave irradiation has been developed. Utilizing this metal-free and eco-friendly protocol, we have prepared various diaryl sulfones in high yields and shorter reaction times under mild conditions. Furthermore, the coupling of diaryliodonium with arenesulfinate salts with and without copper iodide provides a convenient access to various diaryl sulfones with high selectivity. Georg Thieme Verlag Stuttgart · New York.

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.

Novel C-H functionalization of arenes: Palladium-catalyzed synthesis of diaryl sulfides

A novel protocol for the direct arylthiolation of electron-rich arenes is described. Applying arylsulfonyl cyanides in the presence of catalytic amounts of Pd allows for a straightforward synthesis of diaryl sulfides.

Sulfonylation of arenes with sulfonamides

In the presence of triflic anhydride, sulfonylation of arenes with sulfonamides proceeded smoothly in Cl2CHCHCl2 at 80-140 °C, which gave rise to the desired products in good to excellent yields.

Highly selective catalytic Friedel-Crafts sulfonylation of aromatic compounds using a FeCl3-based ionic liquid

Friedel-Crafts sulfonylation of aromatic compounds was carried out using FeCl3-based ionic liquid. These liquids serve as efficient media as well as Lewis acid catalyst.