1028-19-9

Basic information

• Product Name: 1-(4'-methylbenzenesulfonyl)-1H-benzo[d][1.2.3]triazole
• Synonyms: 1-(4'-methylbenzenesulfonyl)-1H-benzo[d][1.2.3]triazole
• CAS NO: 1028-19-9
• Molecular Weight: 273.315
• Mol File: 1028-19-9.mol

Chemical Properties

• CAS DataBase Reference: 1-(4'-methylbenzenesulfonyl)-1H-benzo[d][1.2.3]triazole(CAS DataBase Reference)
• NIST Chemistry Reference: 1-(4'-methylbenzenesulfonyl)-1H-benzo[d][1.2.3]triazole(1028-19-9)
• EPA Substance Registry System: 1-(4'-methylbenzenesulfonyl)-1H-benzo[d][1.2.3]triazole(1028-19-9)

Safety Data

• Hazardous Substances Data: 1028-19-9(Hazardous Substances Data)

Upstream product

• 6380-13-8 4-methyl-N-(2-nitrophenyl)benzene sulfonamide 
• 88-74-4 2-nitro-aniline 
• 98-59-9 p-toluenesulfonyl chloride 
• 3624-90-6 N-tosyl-1,2-diaminobenzene 
• 95-14-7 1,2,3-Benzotriazole 
• 824-79-3 sodium 4-methylbenzenesulfinate 
• 462-80-6 benzyne 
• 941-55-9 4-toluenesulfonyl azide 
• 21050-95-3 N-chlorobenzotriazole 
• 4294-57-9 para-methylphenylmagnesium bromide 
• 536-57-2 p-toluene sulfinic acid 

Downstream Products

• 941-55-9 4-toluenesulfonyl azide 
• 68-34-8 phenyl toluenesulfonamide 
• 7510-48-7 N-(3-bromophenyl)-4-methyl-benzenesulfonamide 
• 95-14-7 1,2,3-Benzotriazole 
• 77597-96-7 α-(4-tolylsulfonyl)phenylacetonitrile 
• 161768-42-9 N-[(E)-1-(1H-1,2,3-benzotriazol-1-yl)(phenyl)methylidene]aniline 
• 161768-52-1 (E)-N-(1-(1H-benzo[d][1,2,3]triazol-1-yl)ethylidene)aniline 
• 104368-08-3 α-<(4-methylphenyl)sulfonyl>benzeneacetic acid ethyl ester 
• 76283-77-7 1-benzenesulfonylmethanesulfonyl-4-methylbenzene 
• 4703-22-4 N-tosylpiperidine 

Relevant articles and documents

One-pot synthesis of N-imidoylbenzotriazoles via benzotriazole-mediated Beckmann rearrangement of oximes

(Matrix presented) N-Imidoylbenzotriazoles 5a-I are obtained under mild conditions in variable yields (20-87%) by reactions of oximes 2a-I with BtTs 1 via a Beckmann rearrangement.

Convenient sulfonylation of benzotriazoles with the in situ–generated sulfonyl bromides

A convenient procedure is developed for the preparation of N-sulfonylbenzotriazoles from sodium sulfinates, benzotriazoles, and sodium bromide in the present of m-chloroperbenzoic acid as oxidant. This radical sulfonylation proceeds efficiently at room te

Synthesis of sulfonyl azides

1-(Alkylsulfonyl)- and 1-(arylsulfonyl)benzotriazoles react with sodium azide in acetonitrile to give the corresponding alkanesulfonyl and arenesulfonyl azides. Georg Thieme Verlag Stuttgart.

Sodium hydrogen exchanger inhibitory activity of benzotriazole derivatives

Series of benzotriazole derivatives were synthesized and evaluated for their Sodium hydrogen exchanger-1 inhibitory potential. All compounds inhibit Sodium hydrogen exchanger-1 in the in-vitro platelet swelling assay. This is perhaps the first report of NHE-1 inhibitory activity of benzotriazole. The 1-alkyl benzotriazole derivatives were found to be more active than the 2-alkyl isomers. The activity increases with increase in chain length of alkyl moiety. Potency increased from that of benzotriazole (IC50= 192.68 μM) to heptyl derivative (compound 13; IC50= 59.23 μM). Introduction of electronegative oxygen atom further increased potency as shown by the benzoyl (compound 16, IC50= 51.57 μM) and sulfonyl groups (compound 17, IC50= 50.89 μM; compound 18, IC50= 49.95 μM).

Nickel-Catalyzed Reductive Cross-Coupling of N-Acyl and N-Sulfonyl Benzotriazoles with Diverse Nitro Compounds: Rapid Access to Amides and Sulfonamides

Herein we report a Ni-catalyzed reductive transamidation of conveniently available N-acyl benzotriazoles with alkyl, alkenyl, and aryl nitro compounds, which afforded various amides with good yields and a broad substrate scope. The same catalytic reaction conditions were also applicable for N-sulfonyl benzotriazoles, which could undergo smooth reductive coupling with nitroarenes and nitroalkanes to afford the corresponding sulfonamides.

Transition-Metal-Free and Visible-Light-Mediated Desulfonylation and Dehalogenation Reactions: Hantzsch Ester Anion as Electron and Hydrogen Atom Donor

Novel approaches for N- and O-desulfonylation under room temperature (rt) and transition-metal-free conditions have been developed. The first methodology involves the transformation of a variety of N-sulfonyl heterocycles and phenyl benzenesulfonates to the corresponding desulfonylated products in good to excellent yields using only KOtBu in dimethyl sulfoxide (DMSO) at rt. Alternately, a visible light method has been used for deprotection of N-methyl-N-arylsulfonamides with Hantzsch ester (HE) anion serving as the visible-light-absorbing reagent and electron and hydrogen atom donor to promote the desulfonylation reaction. The HE anion can be easily prepared in situ by reaction of the corresponding HE with KOtBu in DMSO at rt. Both protocols were further explored in terms of synthetic scope as well as mechanistic aspects to rationalize key features of desulfonylation processes. Furthermore, the HE anion induces reductive dehalogenation reaction of aryl halides under visible light irradiation.

Synthesis of Structurally Diverse Benzotriazoles via Rapid Diazotization and Intramolecular Cyclization of 1,2-Aryldiamines

An operationally simple method has been developed for the preparation of N-unsubstituted benzotriazoles by diazotization and intramolecular cyclization of a wide range of 1,2-aryldiamines under mild conditions, using a polymer-supported nitrite reagent and p-tosic acid. The functional group tolerance of this approach was further demonstrated with effective activation and cyclization of N-alkyl, -aryl, and -acyl ortho-aminoanilines leading to the synthesis of N1-substituted benzotriazoles. The synthetic utility of this one-pot heterocyclization process was exemplified with the preparation of a number of biologically and medicinally important benzotriazole scaffolds, including an α-amino acid analogue.

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.

Synthesis of sulfonamides from azoles and sodium sulfinates at ambient temperature

NBS or NIS mediated direct S[sbnd]N bond formation between azoles and sodium sulfinates is described. The reaction shows good substrate scope and tolerates a wide range of functionalities in both azoles and sodium sulfinate substrates. Pyrazoles are also suitable for this method, various 4-halopyrazoles derivatives were obtained by using N-halosuccinimide (NXS) as the halogen source.

Iodine-catalyzed N-sulfonylation of benzotriazoles with sodium sulfinates under mild conditions

A new and convenient procedure is developed for the preparation of N-sulfonylbenzotriazoles from sodium sulfinates and benzotriazoles using molecular iodine as catalyst via the S[sbnd]N bond formation reaction. This catalytic radical sulfonylation proceed