24906-63-6

Usage

Uses

Used in Organic Synthesis:
2,4,6-Trimethylbenzenesulfonic acid azide is used as a reagent in organic synthesis for its role in azide-alkyne cycloaddition reactions, which are crucial for the formation of triazoles. This application is significant in the creation of complex organic molecules and structures.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 2,4,6-Trimethylbenzenesulfonic acid azide is utilized as a reagent in the synthesis of heterocyclic compounds and pharmaceutical intermediates. Its contribution to the development of new drugs and medicinal compounds is valuable due to its ability to facilitate key chemical reactions in the synthesis process.
Used in Research and Development:
2,4,6-Trimethylbenzenesulfonic acid azide is also employed in research and development settings where its unique reactivity and properties are explored for potential applications in new chemical processes or as part of innovative synthetic pathways. Its use in these areas can lead to advancements in chemical science and technology.

InChI:InChI=1/C9H12N3O2S/c1-6-4-7(2)9(8(3)5-6)15(13,14)12-11-10/h4-5,10H,1-3H3/q+1

Upstream product

• 3453-83-6 mesitylene sulfonic acid 
• 384-98-5 2,4,6-trimethylbenzene-1-sulfonyl fluoride 
• 16182-15-3 2,4,6-trimethylbenzenesulfonohydrazide 
• 4543-58-2 2,4,6-trimethylbenzenesulfonamide 
• 773-64-8 2-mesitylenesulphonyl chloride 

Downstream Products

• 24906-65-8 N-dodecyl-2,4,6-trimethylbenzenesulfonamide 
• 62533-28-2 N-Cyclohexylmesitylen-2-sulfonamid 
• 62533-29-3 N,N’-bis(2,4,6-trimethylphenyl)sulfamide 
• 5692-66-0 2,2',4,4',6,6'-hexamethylazobenzene 
• 38488-43-6 N-[2-Diazo-1-diethylamino-eth-(E)-ylidene]-2,4,6-trimethyl-benzenesulfonamide 
• 1071654-24-4 C₁₄H₂₂N₂O₂S 
• 1128109-95-4 methyl 3-(ethoxycarbonyl)-3-hydroxy-N-(mesitylsulfonyl)-2-phenylpropionimidate 
• 1357445-11-4 (S,E)-(-)-N'-(mesitylsulfinyl)-N,N-dimethyl-2-oxo-2-phenylacetamidine 
• 1357444-98-4 (E)-2-diazo-N'-(mesitylsulfonyl)-N,N-dimethyl-2-phenylacetamidine 
• 1562570-20-0 3-(mesitylsulfonyl)-4-methyl-3,4-dihydro-[1,2,3]triazolo[4,5-b]indole 
• 25116-87-4 2,4,6-trimethyl-N-phenylbenzenesulfonamide 
• 1623807-52-2 N-(2-(1H-pyrrol-1-yl)ethyl)-N-((1-(mesitylsulfonyl)-1H-1,2,3-triazol-4-yl)methyl)-4-methylbenzenesulfonamide 
• 1612143-23-3 (Z)-3-(mesitylsulfonyl)-5-phenyl-3,7,8,9-tetrahydro-2H-1,6,3-dioxazonine 

Relevant academic research and scientific papers

Convenient synthesis of spiroindolenines from tryptamine-derived isocyanides and organic azides by cobalt catalysis in pure water

A Co-catalyzed coupling of 3-(2-isocyanoethyl)indoles with organic azides in pure water for accessing spiroindolenine derivatives was developed. This strategy features mild reaction conditions, high atom-economy, excellent yields, wide substrate scopes, and broad functional group tolerance. The products were obtained simply by sequential operation involving extraction, concentration, precipitation, and filtration, without tedious column chromatography. More importantly, the aqueous catalytic system could be recycled at least ten times without reducing the catalytic activity. The strategy provides a green and efficient method for the construction of spiroindolenine derivatives.

One-pot synthesis of sulfonyl-1H-1,2,3-triazolyl-thiomorpholine 1,1-dioxide derivatives and evaluation of their biological activity

A one-pot procedure for the synthesis of novel 1,2,3-triazole derivatives (5a–5l) in good yields (63 to 77%) using different sulfonic acids and 4-(prop-2-yn-1-yl)thiomorpholine 1,1-dioxide through the in situ generated sulfonyl azides was developed. The structures of the newly synthesized compounds were confirmed by 1H NMR, 13C NMR, mass spectrometry, and elemental analysis. The newly synthesized compounds were screened for in?vitro antibacterial activity and free radical scavenging activity in terms of hydrogen donating or radical scavenging ability by the DPPH method. Among all, the compound N-(4-((4-((1,1-dioxidothiomorpholino) methyl)-1H-1,2,3-triazol-1-yl)sulfonyl)phenyl) acetamide (5l) was found to exhibit potent activity as compared to the standard drugs.

One-Pot Copper-Catalyzed Three-Component Reaction of Sulfonyl Azides, Alkynes, and Allylamines to Access 2,3-Dihydro-1 H-imi-dazo[1,2-a]indoles

A copper-catalyzed multicomponent reaction of sulfonyl azides, alkynes, and allylamines affording 2,3-dihydro-1 H-imidazo-[1,2-a]indoles in moderate yields is reported. Four C-N bonds are constructed- by way of azide-alkyne cycloaddition (CuAAC) and double Ullmann-type coupling reactions in a one-pot process.

Visible-Light-Mediated Sulfonylimination of Tertiary Amines with Sulfonylazides Involving Csp3-Csp3 Bond Cleavage

Visible-light-induced cross-coupling of arylsulfonyl azides with tertiaryamines in the presence of Eosin Y at room temperature has been achieved. This transformation features alkyl C-C bond cleavage and provides a green approach to N-sulfonylamidines under mild conditions.

Tert -Butyl nitrite mediated nitrogen transfer reactions: Synthesis of benzotriazoles and azides at room temperature

A conversion of o-phenylenediamines into benzotriazoles was achieved at room temperature using tert-butyl nitrite. The optimized conditions are also well suited for the transformation of sulfonyl and acyl hydrazines into corresponding azides. This protocol does not require any catalyst or acidic medium. The desired products were obtained in excellent yields in a short span of time.

Manganese-Catalyzed ortho-C-H Amidation of Weakly Coordinating Aromatic Ketones

An efficient manganese-catalyzed ortho-C-H amidation of weakly coordinating aromatic ketones using the readily available sulfonyl azide as the amination reagent is developed. The key step is the ketone directed aromatic metalation using the in situ generated reactive Mn intermediate, MnMe(CO)5. This method offers excellent chemical yields, high regioselectivities, and good functional group tolerance.

Sulfonylative and Azidosulfonylative Cyclizations by Visible-Light-Photosensitization of Sulfonyl Azides in THF

The generation of sulfonyl radicals from sulfonyl azides using visible light and a photoactive iridium complex in THF is described. This process was used to promote sulfonylative and azidosulfonylative cyclizations of enynes to give several classes of highly functionalized heterocycles. The use of THF as the solvent is critical for successful reactions. The proposed mechanism of radical initiation involves the photosensitized formation of a triplet sulfonyl nitrene, which abstracts a hydrogen atom from THF to give a tetrahydrofuran-2-yl radical, which then reacts with the sulfonyl azide to generate the sulfonyl radical.

Synthesis of Sulfonyl Azides via Lewis Base Activation of Sulfonyl Fluorides and Trimethylsilyl Azide

A protocol for the efficient conversion of sulfonyl fluorides into sulfonyl azides through Lewis base activation is described. The in situ generated sulfonyl azides are efficient diazo-transfer agents, affording diazo compounds and primary azides in excellent yields.

Iridium-Catalyzed Direct C-H Sulfamidation of Aryl Nitrones with Sulfonyl Azides at Room Temperature

Ir(III)-catalyzed direct C-H sulfamidation of aryl nitrones has been developed to synthesize various sulfamidated nitrones in moderate to excellent yields with excellent regioselectivity and broad functional group tolerance. This transformation could proceed smoothly at room temperature with low catalyst loading in the absence of external oxidants, acids, or bases. Molecular nitrogen was released as the sole byproduct, thus providing an environmentally benign sulfamidation process. And this protocol could efficiently apply to synthesize the substituted benzisoxazoline via one-step transformation from the product.

Direct synthesis of sulfonyl azides from sulfonic acids

A one-pot process for the synthesis of various sulfonyl azides (RSO2N3) by treating sulfonic acids with triphenylphosphine/trichloroisocyanuric acid/sodium azide at room temperature is described. A wide range of arenesulfonyl and alkanesulfonyl azides was obtained in excellent yields under mild conditions.