80-16-0

Basic information

• Product Name: Chloramine-B
• Synonyms: Benzenesulfochloramide;N-Chlorobenzenesulfonamide;Phenylsulfamyl chloride
• CAS NO: 80-16-0
• Molecular Formula: C₆H₆ClNO₂S
• Molecular Weight: 191.63534
• Mol File: 80-16-0.mol
• Article Data: 6

Chemical Properties

• Boiling Point: 303.8 °C at 760 mmHg
• Flash Point: 137.6 °C
• Appearance: /
• Density: 1.42 g/cm³
• Vapor Pressure: 0.000908mmHg at 25°C
• Refractive Index: 1.566
• CAS DataBase Reference: Chloramine-B(CAS DataBase Reference)
• NIST Chemistry Reference: Chloramine-B(80-16-0)
• EPA Substance Registry System: Chloramine-B(80-16-0)

Safety Data

• Hazardous Substances Data: 80-16-0(Hazardous Substances Data)

Usage

InChI:InChI=1/C6H6ClNO2S/c7-8-11(9,10)6-4-2-1-3-5-6/h1-5,8H

Upstream product

• 24948-81-0 chloro-diisopropyl-amine 
• 98-10-2 benzenesulfonamide 
• 473-29-0 N,N-Dichlorobenzenesulfonamide 
• 107-19-7 propargyl alcohol 
• 624-65-7 2-propynyl chloride 

Downstream Products

• 298-12-4 Glyoxilic acid 
• 82238-25-3 trans-9-Phenylselenoxanthene-N-(benzenesulfonyl)selenilimine 
• 82238-25-3 cis-9-Phenylselenoxanthene-N-(benzenesulfonyl)selenilimine 
• 100-52-7 benzaldehyde 
• 552-89-6 2-nitro-benzaldehyde 
• 22938-45-0 N,N'-bis-benzenesulfonyl-C-phenyl-methanesulfinamidine 

Relevant articles and documents

Axinellamines as broad-spectrum antibacterial agents: Scalable synthesis and biology

Antibiotic-resistant bacteria present an ongoing challenge to both chemists and biologists as they seek novel compounds and modes of action to out-maneuver continually evolving resistance pathways, especially against Gram-negative strains. The dimeric pyrrole-imidazole alkaloids represent a unique marine natural product class with diverse primary biological activity and chemical architecture. This full account traces the strategy used to develop a second-generation route to key spirocycle 9, culminating in a practical synthesis of the axinellamines and enabling their discovery as broad-spectrum antibacterial agents, with promising activity against both Gram-positive and Gram-negative bacteria. While their detailed mode of antibacterial action remains unclear, the axinellamines appear to cause secondary membrane destabilization and impart an aberrant cellular morphology consistent with the inhibition of normal septum formation. This study serves as a rare example of a natural product initially reported to be devoid of biological activity surfacing as an active antibacterial agent with an intriguing mode of action.

Kinetics and mechanism of the reaction of α-phenoxypropanoic acids with sodium salt of N-chlorobenzene-sulphonamide: EDTA catalysis

EDTA smoothly catalyses the oxidation cum chlorination of some 17 α-phenoxypropanoic acids with sodium salt of N-chlorobenzenesulphonamide in acidic solution. A ternary intermediate can be envisaged for describing the enhanced reactivity. Imperfections are observed in the linear Hammett relationship in the case of-NO2 substituents, irrespective of the position. The susceptibility constant, p(≈ + 1) indicates the development of an electron-rich transition state.

REACTION OF N,N-DICHLOROBENZENESULFONAMIDE WITH 3-CHLORO-1-PROPYNE

The reaction of N,N-dichlorobenzenesulfonamide with 3-chloro-1-propyne gives 2,2,3-trichloro-1,1-di(benzenesulfonamido)propane and N-(2,3-dichloro-1-propenyl)benzenesulfonamide. These are the products from consecutive transformations, i.e., addition of N,N-dichlorobenzenesulfonamide to 3-chloro-1-propyne with the formation of N-chloro-N-(2,3-dichloro-1-propenyl)benzenesulfonamide, its reduction to N-(2,3-dichloro-1-propenyl)benzenesulfonamide or transformation by 1,3-migration of a chlorine atom to N-(2,2,3-trichloropropylidene)benzenesulfonamide, and addition of benzenesulfonamide to the latter with the formation of 2,2,3-trichloro-1,1-di(benzenesulfonamido)propane.