585-47-7

Usage

Uses

Used in Pharmaceutical Industry:
1,3-Benzenedisulfonyl chloride is used as a pharmaceutical intermediate for the synthesis of various drugs. Its chemical properties make it a versatile building block in the development of new pharmaceutical compounds, contributing to the advancement of medicinal chemistry.
Used in Chemical Synthesis:
1,3-Benzenedisulfonyl chloride is also used in the chemical synthesis of other organic compounds, such as dyes, plastics, and resins. Its reactivity allows for the creation of a wide range of products with diverse applications across various industries.

Purification Methods

Crystallise it from CHCl3 (EtOH free, by passing through an alumina column) or *C6H6/pet ether and dry it at 20mm pressure. [Beilstein 11 IV 553.]

InChI:InChI=1/C6H4Cl2O4S2/c7-13(9,10)5-2-1-3-6(4-5)14(8,11)12/h1-4H

Upstream product

• 626-04-0 3-mercaptothiophenol 
• 71-43-2 benzene 
• 831-59-4 1,3-benzenedisulfonic acid disodium salt 
• 515-42-4 sodium phenylsulfonate 
• 121-47-1 3-aminobenzenesulfonic acid 
• 142-08-5 2-hydroxypyridin 
• 98-09-9 benzenesulfonyl chloride 

Downstream Products

• 21538-09-0 1,3-bis-(aziridine-1-sulfonyl)-benzene 
• 34577-43-0 benzene-1,3-disulfonic acid dimethyl ester 
• 72672-85-6 3,3'-diethyl-2,2'-dimethyl-4,4'-(benzene-1,3-disulfonyl)-bis-thiomorpholine 
• 34577-48-5 benzol-1,3-disulfonsaeure diethylester 
• 5285-93-8 1,3-dithiocyanatobenzene 
• 116405-68-6 C₆₂H₆₀N₄O₂₀S₈^(4-) 
• 7552-55-8 1,3-benzenedisulfonyl difluoride 
• 148344-35-8 3-Chlorosulfonyl-benzenesulfonic acid 
• 166967-44-8 1,3-bis[N,N-bis[2-(tert-butyldimethylsilyloxy)ethyl]sulfamoyl]benzene 
• 222170-69-6 1,3-benzenedisulfonamide-N,N'-bis(diphenyl) 
• 626-04-0 3-mercaptothiophenol 
• 98-48-6 benzene-1,3-disulfonic acid 
• 16574-26-8 benzene-1,3-disulfinic acid 

Relevant academic research and scientific papers

Supramolecular ionic networks with superior thermal and transport properties based on novel delocalized di-anionic compounds

Supramolecular ionic networks based on highly delocalized dianions having (trifluoromethane-sulfonyl)imide, (propylsulfonyl)methanide and (cyano-propylsulfonyl)imide groups were developed and their physical properties were examined in detail. Most of the synthesized compounds were semi-crystalline possessing Tm values close to 100°C; however, amorphous networks were also obtained using aromatic asymmetric dianions. Rheological measurements in temperature sweep tests at a constant frequency confirmed two different behaviors: a fast melting close to the Tm for semi-crystalline materials and a thermoreversible network for liquid transition for the amorphous supramolecular ionic networks. It was found that the amorphous ionic networks showed significantly higher ionic conductivity (10-3 S cm-1 at 100°C) than the crystalline ionic networks (10-6 S cm-1) and previously reported amorphous citrate ionic networks (10-5 S cm-1). The supramolecular ionic networks containing hydrophobic (trifluoromethanesulfonyl)imide groups demonstrated improved water stability and higher thermal stability than the previously synthesized carboxylate ones. Noticeably, the obtained amorphous supramolecular ionic networks combine not only high ionic conductivity and thermal stability, but also self-healing properties into the same material.

Copper iodide nanoparticles-decorated porous polysulfonamide gel: As effective catalyst for decarboxylative synthesis of N-Arylsulfonamides

A porous cross-linked poly (ethyleneamine)-polysulfonamide (PEA-PSA) as a novel organic support system is synthesized in the presence of silica template by nanocasting technique. The paper demonstrates immobilization of CuI nanoparticles inside the pores (PEA-PSA?CuI) for the facile recovery and recycling of these nanoparticles. The presence of porous PEA-PSA and PEA-PSA?CuI nanocomposites was confirmed using FT-IR spectroscopy, FE-SEM, EDX, TGA, XRD, TEM, BET, XPS, WDX, 1H NMR, and ICP-OES techniques. The PEA-PSA?CuI along with Ag(I)/K2S2O8 was implemented as a reusable cooperative catalyst-oxidant system in the N-arylation of p-toluenesulfonamide with substituted carboxylic acids in mild condition. So, the novel decarboxylative cross-coupling catalyzed by copper and silver has been developed. Aromatic, secondary and tertiary aliphatic acids underwent high efficient decarboxylative processes with p-toluenesulfonamide to afford the corresponding products. This method provides a practical approach for the flexible synthesis of sulfonamides from the readily affordable substrates. The catalyst is highly reusable and efficient, especially in terms of time and yield of the desired product.

Sulfur–Fluoride Exchange (SuFEx)-Mediated Synthesis of Sterically Hindered and Electron-Deficient Secondary and Tertiary Amides via Acyl Fluoride Intermediates

Amide bond formation is one of the most executed reactions in chemistry and biology. This is largely due to the ubiquity of the amide functional group in biological molecules, natural products and pharmaceutically important drugs. We report here the development of “SuFExAmide”: a new sulfur–fluoride exchange (SuFEx) click chemistry based protocol for the efficient amidation of carboxylic acids via acyl fluoride intermediates. We have developed benzene-1,3-disulfonyl fluoride as a cost effective, powerful and versatile coupling agent, which delivers challenging secondary and tertiary amides in excellent yields from sterically hindered and electron-deficient amines. The straightforward method offers significant benefits over existing protocols in terms of substrate scope, efficiency and ease of operation and is demonstrated by the synthesis of 44 amides, including GNF6702, an antiprotozoal drug candidate. In the majority of cases, the amide products are obtained in high yield without the need for excess reagents or chromatographic purification.

A general simple methodology for synthesis of isonitriles using benzene-1,3-disulfonyl dichloride

Isonitrile derivatives have been synthesized in good to high yields by dehydration of aliphatic and aromatic formamides in the presence of benzene-1,3-disulfonyl dichloride as easy and efficient reagent.

HEPATITIS B ANTIVIRAL AGENTS

The present invention includes a method of inhibiting, suppressing or preventing HBV infection in an individual in need thereof, comprising administering to the individual a therapeutically effective amount of at least one compound of the invention.

SOLUBLE DIAZOALKANE PRECURSORS

The present invention relates to compounds useful in the preparation of diazoalkanes in general (such as diazomethane, diazoethane, diazopropane, diazobutane and homologues) and to diazomethane (CH2=N=N) in particular. The compounds chosen as the diazomethane source according to the invention also have the advantage of being water soluble. They are capable of being decomposed to diazomethane or another diazoalkane (which is allowed to bubble out of the vessel to another vessel containing a solution of reactant) and are converted to by-products that are also water-soluble.

Mild and regioselective bromination of aromatic compounds with N,N,N′,N′-Tetrabromobenzene-1,3-disulfonylamide and poly(N-bromobenzene-1,3-disulfonylamide)

N,N,N′,N′-Tetrabromobenzene-1,3-disulfonylamide (TBBDA) and poly[N-bromobenzene-1,3-disulfonylamide] (PBBS) can be used for the regioselective bromination of aromatic compounds in excellent yields under mild conditions.

N,N′,N,N′-tetrabromo-benzene-1,3-disulfonylamide as a novel reagent for oxidative aromatization of 1,3,5-trisubstituted pyrazolines under heterogeneous and solvent-free conditions

1,3,5-Trisubstituted pyrazolines were converted to the corresponding pyrazoles in good yields under heterogeneous and solvent-free conditions by N,N′,N,N′-tetrabromo-benzene-1,3-disulfonylamide [TBBDA] at ambient temperature.

Mild oxidation of 1,3,5-trisubstituted pyrazolines with N-bromo-sulphonamides

1,3,5-Trisubstituted pyrazolines to pyrazoles are carried out efficiently in the presence of new reagents N,N,N′,N′-tetrabromo-benzene-1,3- disulfonylamine [TBBDA] and N,N′-dibromo-N,N′-1,2-ethanediylbis-(p- toluenesulphonamide) [BNBTS] in solvent-free conditions with catalytic amounts of SiO2 under microwave irradiation in high yields.

Synthetic multimerizing agents

New compounds are disclosed for multimerizing immunophilins and proteins containing immunophilin or immunophilin-related domains. The compounds are of the formulaM-L-Qwhere M is a synthetic ligand for an FKBP protein