6461-76-3

Basic information

• Product Name: 1,2-BENZENEDISULFONYL DICHLORIDE
• Synonyms: 1,2-Benzenedisulfonyl chloride;Benzene-1,2-disulfonic acid dichloride;Benzene-1,2-disulfonic acid dich;1,2-Bis(chlorosulfonyl)benzene;1,2-Di(chlorosulfonyl)benzene;o-(Chlorosulfonyl)benzenesulfonyl chloride;o-Benzenedisulfonyl chloride;o-Bis(chlorosulfonyl)benzene
• CAS NO: 6461-76-3
• Molecular Formula: C₆H₄Cl₂O₄S₂
• Molecular Weight: 275.13
• Product Categories: Protection & Derivatization Reagents (for Synthesis);Synthetic Organic Chemistry;Organic Building Blocks;Sulfonyl Halides;Sulfur Compounds
• Mol File: 6461-76-3.mol
• Article Data: 6

Chemical Properties

• Melting Point: 140-146 °C
• Boiling Point: 394.4 ºC at 760 mmHg
• Flash Point: 192.3 ºC
• Appearance: /
• Density: 1.690
• Vapor Pressure: 1.04E-08mmHg at 25°C
• Refractive Index: 1.581
• Storage Temp.: 2-8°C
• Solubility: very faint turbidity in hot Toluene
• CAS DataBase Reference: 1,2-BENZENEDISULFONYL DICHLORIDE(CAS DataBase Reference)
• NIST Chemistry Reference: 1,2-BENZENEDISULFONYL DICHLORIDE(6461-76-3)
• EPA Substance Registry System: 1,2-BENZENEDISULFONYL DICHLORIDE(6461-76-3)

Safety Data

• Hazard Codes: C
• Statements: 34
• Safety Statements: 26-36/37/39-45
• RIDADR: UN 3261 8/PG 3
• WGK Germany: 3
• F: 9-21
• HazardClass: 8
• PackingGroup: II
• Hazardous Substances Data: 6461-76-3(Hazardous Substances Data)

Usage

General Description

1,2-Benzenedisulfonyl dichloride is a chemical compound with the molecular formula C12H6Cl2O4S2. It is a colorless to pale yellow solid that is soluble in various organic solvents. 1,2-Benzenedisulfonyl dichloride is commonly used as a reagent in organic synthesis, particularly in the production of dyes and pharmaceuticals. It is a powerful acylating agent, meaning it can introduce a sulfonyl chloride group to organic molecules. Additionally, 1,2-Benzenedisulfonyl dichloride is also used as a crosslinking agent in the production of polymers and as a catalyst in various chemical reactions. Due to its reactivity and potential hazards, it should be handled and stored with appropriate safety measures in place.

InChI:InChI=1/C19H19ClO3/c1-3-5-16-10-15(12-21)11-18(22-4-2)19(16)23-13-14-6-8-17(20)9-7-14/h3,6-12H,1,4-5,13H2,2H3

Upstream product

• 88-21-1 2-amino-1-benzenesulfonic acid 
• 612-31-7 2-sulfo-benzenediazonium-betaine 
• 408340-56-7 C₁₀H₁₂OS₃ 
• 17534-15-5 Benzene-1,2-dithiol 
• 24569-50-4 2-sulfobenzenediazonium chloride 
• 99862-30-3 1-butylsulfanyl-2-methylsulfanyl-benzene 
• 5710-54-3 o-Benzenedisulfonic acid dipotassium salt 
• 54030-60-3 2-isopropylidene-1,3-benzodithiole 
• 57842-27-0 1,3-benzodithiol-2-ylium tetrafluoroborate 
• 55315-56-5 2-(3-methylbutoxy)-1,3-benzodithiole 
• 62217-32-7 2-diphenylmethylene-1,3-benzodithiole 

Downstream Products

• 21691-12-3 2-phenethyl-benzo[1,3,2]dithiazole 1,1,3,3-tetraoxide 
• 53965-94-9 1,2-Benzoldisulfonsaeure-dicyclohexylamid 
• 204975-87-1 2-(4-Methoxy-benzyl)-benzo[1,3,2]dithiazole 1,1,3,3-tetraoxide 
• 103474-40-4 N'-(4,6-dimethylpyrimidin-2-yl)-N-(2-methoxyaminosulphonylphenylsulphonyl)-S-methyl-isothiourea 
• 1239013-79-6 tert-butyl N-(4-(1,1,3,3-tetraoxidobenzo[d][1,3,2]dithiazol-2-yl)phenyl)carbamate 
• 1239013-74-1 2-(4-((pyridin-2-ylmethyl)amino)phenyl)benzo[d][1,3,2]dithiazole 1,1,3,3-tetraoxide hydrochloride 
• 388620-99-3 C₁₃H₁₁NO₄S₂ 
• 1380349-87-0 C₁₂H₈ClNO₄S₂ 
• 312590-80-0 C₁₃H₁₁NO₅S₂ 
• 27291-97-0 Benzol-o-disulfonsaeure-bismethylamid 
• 53965-87-0 benzol-1,2-disulfonsaeuredianilid 
• 21691-17-8 benzene-1,2-disulfonyl diazide 
• 21691-15-6 Benzene-1,2-disulfonic acid bis-benzylamide 
• 21691-16-7 C₆H₁₀N₄O₄S₂ 

Relevant articles and documents

A new effective synthesis of arene mono- and disulfonyl chlorides

Arene mono- and disulfonyl chlorides have been easily synthesized starting from the corresponding anilines via aqueous oxidative chlorination of S-aryl O-ethyl dithiocarbonates intermediates, aryl methyl sulfides, or from arenethiols. Georg Thieme Verlag Stuttgart.

Selective, Electrophilic Fluorinations Using N-Fluoro-o-benzenedisulfonimide

The synthesis of N-fluoro-o-benzenedisulfonimide (NFOBS, 2) and its use as an "electrophilic" fluorinating reagent with nucleophilic substrates is described and compared with that of N-fluorobenzenesulfonimide (NFSi, 3).NFOBS (2) is prepared in three steps in 81percent overall yield from commercially available o-benzenedisulfonic acid (4) and involves treatment of o-benzenedisulfonimide (6) with dilute fluorine (10percent F2/N2).Reaction of 2 with metal enolates, silyl enol ethers, and 1,3-dicarbonyl compounds affords the corresponding α-fluoro compounds in yields up to 95percent, with good control of mono- and difluorination.Fluorination of ortho-metalated aromatic compounds was achieved in modest to good yields (10-80percent).While the reactivities of 2 and 3 are similar, better yields were observed with the former reagent in the fluorination of metal enolates, Grignard and lithium reagents, while 3 gave better results with the ortho-lithiated aromatic substrates.The available evidence suggests an SN2-type mechanism for the fluorination of nucleophilic substrates by these reagents.

A CONVENIENT SYNTHESIS OF 1,2-BENZENEDISULPHONYL CHLORIDE

A new method for the synthesis of 1,2-benzenedisulphonyl chloride starting from anthranilic acid, via 2-(3-methylbutoxy)-1,3-benzodithiole or 1,3-benzodithiolium tetrafluroborate is described.