13068-60-5

Basic information

• Product Name: N-(2-Benzothiazolyl)benzenesulfonamide
• Synonyms: N-(2-Benzothiazolyl)benzenesulfonamide;N-(1,3-Benzothiazol-2-yl)benzenesulfonamide
• CAS NO: 13068-60-5
• Molecular Formula: C₁₃H₁₀N₂O₂S₂
• Molecular Weight: 290.36
• Mol File: 13068-60-5.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: N-(2-Benzothiazolyl)benzenesulfonamide(CAS DataBase Reference)
• NIST Chemistry Reference: N-(2-Benzothiazolyl)benzenesulfonamide(13068-60-5)
• EPA Substance Registry System: N-(2-Benzothiazolyl)benzenesulfonamide(13068-60-5)

Safety Data

• Hazardous Substances Data: 13068-60-5(Hazardous Substances Data)

Upstream product

• 136-95-8 2-amino-benzthiazole 
• 98-09-9 benzenesulfonyl chloride 
• 473-29-0 N,N-Dichlorobenzenesulfonamide 
• 103-72-0 phenyl isothiocyanate 
• 1886-60-8 benzenesulfonyl-carbonimidic acid dichloride 
• 137-07-5 2-amino-benzenethiol 
• 13068-20-7 N-bis-(methylsulfanylmethylene)benzenesulfonamide 
• 103-70-8 Formanilid 
• 118221-29-7 N-[3-[(E)-Phenyliminomethyl]-3H-benzothiazol-(2Z)-ylidene]-benzenesulfonamide 
• 98-10-2 benzenesulfonamide 
• 2516-40-7 2-bromo-1,3-benzothiazole 

Downstream Products

• 118221-29-7 N-[3-[(E)-Phenyliminomethyl]-3H-benzothiazol-(2Z)-ylidene]-benzenesulfonamide 
• 942116-33-8 [(1,10-phenanthroline)bis(N-(benzothiazol-2-yl)benzenesulfonamidate)copper(II)] 

Relevant articles and documents

Sulfonamidation of Aryl and Heteroaryl Halides through Photosensitized Nickel Catalysis

Herein we report a highly efficient method for nickel-catalyzed C?N bond formation between sulfonamides and aryl electrophiles. This technology provides generic access to a broad range of N-aryl and N-heteroaryl sulfonamide motifs, which are widely represented in drug discovery. Initial mechanistic studies suggest an energy-transfer mechanism wherein C?N bond reductive elimination occurs from a triplet excited NiII complex. Late-stage sulfonamidation in the synthesis of a pharmacologically relevant structure is also demonstrated.

In vitro and in vivo antileishmanial and trypanocidal studies of new N -benzene- and N -naphthalenesulfonamide derivatives

We report in vivo and in vitro antileishmanial and trypanocidal activities of a new series of N-substituted benzene and naphthalenesulfonamides 1-15. Compounds 1-15 were screened in vitro against Leishmania infantum, Leishmania braziliensis, Leishmania gu

Novel solid-phase parallel synthesis of N-substituted-2-aminobenzo [d]thiazole derivatives via cyclization reactions of 2-iodophenyl thiourea intermediate resin

A novel solid-phase methodology has been developed for the synthesis of N-alkyl, N-acyl, and N-sulfonyl-2-aminobenzo[d]thiazole derivatives. The key step in this procedure involves the preparation of polymer-bound 2-aminobenzo[d]thiazole resins 5 by cyclization reaction of 2-iodophenyl thiourea resin 3. The resin-bound 2-iodophenyl thiourea 3 is produced by addition of 2-iodophenyl isothiocyanate 2 to the amine-terminated linker amide resin 1. These core skeleton 2-aminobenzo[d]thiazole resins 5 undergo functionalization reactions with various electrophiles, such as alkyl halides, acid chlorides, and sulfonyl chlorides to generate N-alkyl, N-acyl, and N-sulfonyl-2-aminobenzo[d]thiazole resins 6, 7, and 8, respectively. Finally, N-alkyl, N-acyl, and N-sulfonyl-2-aminobenzo[d]thiazole derivatives 9, 10, and 11 are then generated in good yields and purities by cleavage of the respective resins 6, 7, and 8 using trifluoroacetic acid (TFA) in dichloromethane (DCM).

Genotoxic potential of N-(benzothiazolyl)sulfonamide copper(II) complexes on yeast cells transformed with YEGFP expression constructs containing the RAD54 or RNR2 promoter

Four ternary complexes [Cu(L)2(phen)] where L is an N-(benzothiazol-2-yl)sulfonamide derivative have been prepared and their ability to cleave DNA has been studied. The complexes were structurally characterized with the aid of single-crystal X-ray crystallography. Whereas the molecular structure of the [Cu(L1)2(phen)] (1) [HL1 = N-(6-chlorobenzothiazol- 2-yl)benzenesulfonamide] and [Cu(L3)2(phen)] (3) [HL3 = N-(benzothiazol-2-yl)benzenesulfonamide] complexes can best be described as having a distorted square-planar geometry, that of the [Cu(L4) 2(phen)] (4) [HL4 = N-(benzothiazol-2-yl)toluenesulfonamide] complex shows a strictly square-planar geometry. The [Cu(L2)2(phen)MeOH] (2) [HL2 = N-(6-chlorobenzothiazol-2-yl)toluenesulfonamide] complex displays an axially elongated square-pyramidal coordination geometry in which the phen ligand binds at the basal plane. Viscosity and fluorescence measurements indicated that [Cu(L4)2(phen)] (4) has a propensity for binding calf thymus DNA. The four complexes were found to be efficient chemical nucleases, with ascorbate/H2O2 activation giving rise to hydroxyl and superoxide radicals as active cleaving species. The nuclease activity of 4 is not only the highest of the four complexes, but also much higher than that of the copper-phenanthroline complex. The ability of the complexes to cleave DNA within cells has been tested by monitoring the expression of the yEGFP gene containing reporter plasmid. The significant induction of fluorescence by complex 4 indicates that it is able to cleave DNA inside the cell. Wiley-VCH Verlag GmbH & Co. KGaA, 2006.

VILSMEIER-HAACK REACTION OF 2-AMINO-X-BENZOTHIAZOLES WITH N-PHENYLFORMAMIDE IN THE PRESENCE OF BENZENESULFONYL CHLORIDE

2-Amino-X-benzothiazoles (X = H, 4-Cl, 6-Cl, 6-NO2, 6-CH3, 6-OCH3, 6-Br) react with N-phenylformamide and two equivalents of benzenesulfonyl chloride in pyridine, affording different products in dependence on the substituent X: N-(X-2-benzothiazolyl)formamidines, N-phenyl-N'-(X-2-benzothiazolyl)formamidines, N-phenyl-N',N''-bis(X-2-benzothiazolyl)triaminomethanes, N-(X-2-benzothiazolyl)benzenesulfonamides and N-2-((X-3-phenyliminomethyl)benzothiazolylidene)benzenesulfonamides.In the presence of one equivalent of benzenesulfonyl chloride, benzothiazoles I either do not react or are partially benzenesulfonated.