433-17-0

Basic information

• Product Name: Benzothiazole-2-Sulfonamide
• Synonyms: Benzothiazole-2-Sulfonamide;2-Benzothiazolesulfonamide(6CI,7CI,8CI,9CI);2-benzothiazolesulfonamide;1,3-benzothiazole-2-sulfonamide;Benzo[d]thiazole-2-sulfonaMide
• CAS NO: 433-17-0
• Molecular Formula: C₇H₆N₂O₂S₂
• Molecular Weight: 214.2647
• Product Categories: BENZOTHIAZOLE
• Mol File: 433-17-0.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 430.9 °C at 760 mmHg
• Flash Point: 214.4 °C
• Appearance: /
• Density: 1.584 g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.708
• CAS DataBase Reference: Benzothiazole-2-Sulfonamide(CAS DataBase Reference)
• NIST Chemistry Reference: Benzothiazole-2-Sulfonamide(433-17-0)
• EPA Substance Registry System: Benzothiazole-2-Sulfonamide(433-17-0)

Safety Data

• Hazardous Substances Data: 433-17-0(Hazardous Substances Data)

Usage

General Description

Benzothiazole-2-sulfonamide is a chemical compound with the molecular formula C7H6N2O2S2. It is an important intermediate in the synthesis of various pharmaceuticals and agrochemicals, particularly in the production of sulfa drugs. Benzothiazole-2-sulfonamide has antifungal and antibacterial properties, making it useful in the treatment of microbial infections. It is also used as a corrosion inhibitor and as a dye intermediate. Additionally, it is employed as a rubber additive to improve the wear and aging resistance of rubber products. Benzothiazole-2-sulfonamide is a versatile and valuable compound with a wide range of applications in the chemical and pharmaceutical industries.

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

• 149-30-4 2-thioxo-3H-1,3-benzothiazole 
• 149-30-4 2-Mercaptobenzothiazole 
• 2801-21-0 benzothiazole sulfenamide 
• 2824-46-6 benzothiazole-2-sulfonyl chloride 
• 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 

Downstream Products

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

Relevant articles and documents

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.

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.

Topical carbonic anhydrase inhibitors

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