25116-87-4

Basic information

• Product Name: 2,4,6-trimethyl-N-phenylbenzenesulfonamide
• Synonyms: 2-Mesitylenesulfonanilide
• CAS NO: 25116-87-4
• Molecular Formula: C₁₅H₁₇NO₂S
• Molecular Weight: 275.366
• Mol File: 25116-87-4.mol
• Article Data: 6

Chemical Properties

• Boiling Point: 421°C at 760 mmHg
• Flash Point: 208.4°C
• Density: 1.211g/cm³
• Vapor Pressure: 2.7E-07mmHg at 25°C
• Refractive Index: 1.6
• CAS DataBase Reference: 2,4,6-trimethyl-N-phenylbenzenesulfonamide(CAS DataBase Reference)
• NIST Chemistry Reference: 2,4,6-trimethyl-N-phenylbenzenesulfonamide(25116-87-4)
• EPA Substance Registry System: 2,4,6-trimethyl-N-phenylbenzenesulfonamide(25116-87-4)

Safety Data

• Hazardous Substances Data: 25116-87-4(Hazardous Substances Data)

Usage

Class

Sulfonamide

Common Uses

UV stabilizer in plastics, rubber, and coatings

Function

Absorbs and dissipates UV radiation to prevent damage to materials

Potential Use

Anti-inflammatory agent

Safety Precautions

Proper handling and safety measures should be taken when working with this chemical compound.

Upstream product

• 24906-63-6 2,4,6-trimethylbenzene-1-sulfonyl azide 
• 98-80-6 phenylboronic acid 
• 773-64-8 2-mesitylenesulphonyl chloride 
• 98-95-3 nitrobenzene 
• 62-53-3 aniline 
• 71100-55-5 1-mesitylenesulfonyl-4-nitroimidazole 

Downstream Products

• 542-11-0 aniline hydrobromide 
• 7664-93-9 sulfuric acid 
• 62-53-3 aniline 
• 108-67-8 1,3,5-trimethyl-benzene 

Relevant articles and documents

Synthesis of: N -arylsulfonamides via Fe-promoted reaction of sulfonyl halides with nitroarenes in an aqueous medium

A fascinating Fe-promoted protocol for the synthesis of N-arylsulfonamides has been developed. Starting from commercially available nitroarenes and sulfonyl chlorides, moderate to excellent yields of the corresponding N-arylsulfonamides can be obtained. In particular, Fe dust serves as the sole reductant in the transformation and it can be easily performed on a large scale.

Gas-phase fragmentations of anions derived from N-phenyl benzenesulfonamides

In addition to the well-known SO2 loss, there are several additional fragmentation pathways that gas-phase anions derived from N-phenyl benzenesulfonamides and its derivatives undergo upon collisional activation. For example, N-phenyl benzenesulfonamide fragments to form an anilide anion (m/z 92) by a mechanism in which a hydrogen atom from the ortho position of the benzenesulfonamide moiety is specifically transferred to the charge center. Moreover, after the initial SO2 elimination, the product ion formed undergoes primarily, an inter-annular H2 loss to form a carbazolide anion (m/z 166) because the competing intra-annular H2 loss is significantly less energetically favorable. Results from tandem mass spectrometric experiments conducted with deuterium-labeled compounds confirmed that the inter-ring mechanism is the preferred pathway. Furthermore, N-phenyl benzenesulfonamide and its derivatives also undergo a phenyl radical loss to form a radical ion with a mass-to-charge ratio of 155, which is in violation of the so-called "even-electron rule." [Figure not available: see fulltext.]

Spontaneous resolution of aromatic sulfonamides: Effective screening method and discrimination of absolute structure

(Chemical Equation Presented) An effective screening method combining parallel synthesis and solid-state CD measurements was established to identify achiral aromatic sulfonamides that show spontaneous resolution with rapidity. We found that 4 of the 12 achiral sulfonamides crystallized as chiral crystals through this method. The chirality of each sulfonamide was discriminated by solid-state CD spectra and Flack parameter in an X-ray analysis. Correspondence between the observed Cotton effect and the absolute configuration could be confirmed by time-dependent DFT calculations.