433-17-0

Usage

Uses

Used in Pharmaceutical Industry:
Benzothiazole-2-Sulfonamide is used as an intermediate in the synthesis of various pharmaceuticals, particularly in the production of sulfa drugs. Its antifungal and antibacterial properties make it useful in the treatment of microbial infections.
Used in Agrochemical Industry:
Benzothiazole-2-Sulfonamide is used as an intermediate in the synthesis of various agrochemicals, contributing to the development of effective fungicides and bactericides for agricultural applications.
Used in Corrosion Inhibition:
Benzothiazole-2-Sulfonamide is used as a corrosion inhibitor, helping to protect metal surfaces from corrosion and extending the lifespan of various industrial equipment and structures.
Used in Dye Industry:
Benzothiazole-2-Sulfonamide is used as a dye intermediate, playing a crucial role in the production of various dyes and pigments for different applications.
Used in Rubber Industry:
Benzothiazole-2-Sulfonamide is used as a rubber additive to improve the wear and aging resistance of rubber products, enhancing their durability and performance in various applications.

InChI:InChI=1/C7H6N2O2S2/c8-13(10,11)7-9-5-3-1-2-4-6(5)12-7/h1-4H,(H2,8,10,11)

Upstream product

• 2801-21-0 benzothiazole sulfenamide 
• 149-30-4 2-Mercaptobenzothiazole 
• 184434-18-2 (2E,4S)-4-methylamino-2,5-dimethylhex-2-enoic acid ethyl ester 
• 377779-87-8 (S)-2-(Benzothiazole-2-sulfonylamino)-3,3-dimethyl-butyryl chloride 
• 2824-46-6 benzothiazole-2-sulfonyl chloride 
• 149-30-4 2-thioxo-3H-1,3-benzothiazole 

Downstream Products

• 934-34-9 2-hydroxybenzothiazole 
• 1420372-82-2 O-(benzothiazol-2-yl)-N-methylhydroxylamine 
• 1225035-43-7 C₇H₁₀N₂*C₁₄H₁₀N₂O₄S₂ 

Relevant academic research and scientific papers

Copper-Catalyzed Coupling Reactions of Cyclobutanone Oxime Esters with Sulfur Nucleophiles at Room Temperature

A copper-catalyzed iminyl radical-mediated C-C bond cleavage/cross-coupling tandem reaction of cyclobutanone oxime esters with aryl thiols in the presence of 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) at room temperature was developed, and aryl cyanopropyl sulfides were smoothly synthesized in 20-88% yields. By altering the copper reagent and the molar ratio of cyclobutanone oxime ester/aryl thiol/DBU, substitutional product N-arylthio cyclobutanone imines were selectively generated in 50-91% yields. Using this protocol, C-S bond and N-S bond formations using aryl thiols as sulfur sources were realized under very mild conditions without the use of photocatalysis and electrocatalysis techniques.

N-Sulfonylcarboxamide as an Oxidizing Directing Group for Ruthenium-Catalyzed C–H Activation/Annulation

N-Sulfonylcarboxamides can act as both a directing group for C–H activation and an internal oxidant in the Ru-catalyzed annulation reaction with alkynes to give isoquinolones. Of all of the N-sulfonylcarboxamides that were studied, the N-(2,6-difluorophenyl)sulfonamide derivatives were found to be the most efficient and led to the formation of an unstable sulfinate byproduct that decomposed into 1,3-difluorobenzene under the reaction conditions. The described isoquinolone synthesis provides an alternative to the currently known traceless annulations of hydroxamic acid and sulfoximine derivatives.

Hydroxylamine as an oxygen nucleophile: Substitution of sulfonamide by a hydroxyl group in benzothiazole-2-sulfonamides

Benzothiazole-2-sulfonamides react with an excess of hydroxylamine in aqueous solutions to form 2-hydroxybenzothiazole, sulfur dioxide, and the corresponding amine. Mechanistic studies that employ a combination of structure-reactivity relationships, oxygen labeling experiments, and (in)direct detection of intermediates and products reveal that the reaction proceeds via oxygen attack, and that oxygen incorporated in the 2-hydroxybenzothiazole product derives from hydroxylamine. The reaction, which is performed under mild conditions, can be used as a deprotection method for cleavage of benzothiazole-2-sulfonyl-protected amino acids.

A total synthesis of (-)-hemiasterlin using N-Bts methodology

A total synthesis of (-)-hemiasterlin has been accomplished in nine steps from 258 (>35% yield overall). An improved enantiocontrolled route to the tetramethyltryptophan subunit 32 was developed using an asymmetric Strecker synthesis (five steps, 50% yield from 25), and the dipeptide 22 was prepared in seven steps, 37% yield from valinol. The synthesis exploits the high reactivity of a Bts-protected amino acid chloride in the difficult peptide coupling of sterically hindered amino acid residues 18 and 20 to form 21 (70%, recrystallized) and also uses N-Bts intermediates for the high-yielding N-methylations of 14 and 31. In addition, the Bts-protected di-tert-butyl N-acylimidodicarbonate 33 is shown to undergo efficient coupling with 22 to form 34 (97% in the coupling step; 79% over the activation; coupling sequence from 32).