Chloramine-B

Base Information

• Chemical Name: Chloramine-B
• CAS No.: 80-16-0
• Molecular Formula: C6H6ClNO2S
• Molecular Weight: 191.638
• UNII: 59521MS4CG
• DSSTox Substance ID: DTXSID60229992
• Nikkaji Number: J787.366B
• Wikidata: Q27261655
• Mol file: 80-16-0.mol

Synonyms:chloramin B;chloramine B;chloramine-B;chloramine-B, lithium salt;chloramine-B, potassium salt;chloramine-B, sodium salt;Chlordetal;N-chlorobenzenesulfonamide;phenylsulfamyl chloride

Chemical Property of Chloramine-B

Chemical Property:

• Vapor Pressure: 0.000908mmHg at 25°C
• Melting Point: 170-173oC
• Refractive Index: 1.566
• Boiling Point: 303.8 °C at 760 mmHg
• Flash Point: 137.6 °C
• PSA: 54.55000
• Density: 1.42 g/cm³
• LogP: 2.59040
• XLogP3: 1.3
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 190.9807773
• Heavy Atom Count: 11
• Complexity: 203

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Other Uses -> Biocides/Disinfectants
• Canonical SMILES: C1=CC=C(C=C1)S(=O)(=O)NCl
• General Description: Chloramine-B (Benzenesulfochloramide, N-Chlorobenzenesulfonamide, or Phenylsulfamyl chloride) serves as both an oxidant and a nitrogen source in iodine-catalyzed C-H amidation and imination reactions, enabling the regioselective functionalization of 2,3-disubstituted indoles at the 2α-position. It facilitates the synthesis of 2α-nitrogen-containing indole derivatives, which are valuable in bioactive compound and alkaloid synthesis, under mild conditions without requiring external oxidants. The proposed mechanism involves an iminium intermediate, with N-iodo-chlorobenzenesulfonamide acting as a key reactive species.

Technology Process of Chloramine-B

There total 4 articles about Chloramine-B which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 100.0%

benzenesulfonamide (98-10-2) → N-chlorobenzenesulfonamide (80-16-0)

Guidance literature:

With 2-chloro-1,3-bis(t-butoxycarbonyl)guanidine; In dichloromethane; at 23 ℃; for 1.16667h;

DOI:10.1021/ja508632y

Reference yield: 32.0%

N,N-Dichlorobenzenesulfonamide (473-29-0) + propargyl alcohol (107-19-7) → benzenesulfonamide (98-10-2) + N-chlorobenzenesulfonamide (80-16-0) + 2-propynyl chloride (624-65-7) + 3-hydroxy-2,2-dichloro-1,1-di(N-benzenesulfonamide)propane

Guidance literature:

In tetrachloromethane; at 30 - 35 ℃; for 6h; Irradiation;

Reference yield: 32.0%

N,N-Dichlorobenzenesulfonamide (473-29-0) + 2-propynyl chloride (624-65-7) → benzenesulfonamide (98-10-2) + N-chlorobenzenesulfonamide (80-16-0) + N-(2,3-di-2-chloro-1-propenyl)benzenesulfonamide + 2,2,3-trichloro-1,1-di(benzenesulfonamido)propane

Guidance literature:

In tetrachloromethane; at 35 - 40 ℃; for 18h; Irradiation;

upstream raw materials:

benzenesulfonamide

chloro-diisopropyl-amine

N,N-Dichlorobenzenesulfonamide

2-propynyl chloride

Downstream raw materials:

Glyoxilic acid

4-methyl-benzaldehyde

trans-9-Phenylselenoxanthene-N-(benzenesulfonyl)selenilimine

cis-9-Phenylselenoxanthene-N-(benzenesulfonyl)selenilimine

Refernces

Iodine-Catalyzed C-H Amidation and Imination at the 2α-Position of 2,3-Disubstituted Indoles with Chloramine Salts

10.1021/acs.joc.8b00286

The research focuses on the development of an iodine-catalyzed C-H amidation and imination reaction at the 2α-position of 2,3-disubstituted indoles using chloramine salts. The study outlines a novel and efficient method for the synthesis of 2α-nitrogen-containing indole derivatives, which are important scaffolds in bioactive compounds and indole alkaloids. The experiments involved the optimization of reaction conditions using various iodine sources and solvents, ultimately achieving high regioselectivity and yield under ambient conditions without the need for external oxidants. Chloramine salts, specifically chloramine-B (2a) was used as both oxidants and nitrogen sources in the reaction. The substrate scope was extensively explored, demonstrating the versatility of the method with a range of indole derivatives. The reaction's mechanism was also investigated, suggesting the involvement of an iminium intermediate and a plausible pathway involving N-iodo-chlorobenzenesulfonamide as an active species. The synthetic value of the method was further demonstrated by a concise synthesis of the bridged tetracyclic framework of akuammiline alkaloids. Analytical techniques such as NMR, HRMS, and X-ray diffraction were employed to characterize the products and confirm the structure of the synthesized compounds.