119752-83-9

Basic information

• Product Name: 1,4-Diazabicyclo[2.2.2]octane-1,4-diium-1,4-disulfinate
• Synonyms: 1,4-Diazabicyclo[2.2.2]octane-1,4-diium-1,4-disulfinate;1,4-Diazabicyclo[2.2.2]octane bis(sulfur dioxide) adduct;1,4-Diazabicyclo[2.2.2]octane bis(sulfur dioxide) adduct >=95% (sulfur, eleMental analysis);DABSO;1,4-Diazoniabicyclo[2.2.2]octane-1,4-disulphinate;1,4-Diazoniabicyclo[2.2.2]octane-1,4-disulfinate;Bis(sulfur Dioxide)-1,4-diazabicyclo[2.2.2]octane Adduct
• CAS NO: 119752-83-9
• Molecular Formula: C₆H₁₂N₂O₄S₂
• Molecular Weight: 240.30048
• Mol File: 119752-83-9.mol
• Article Data: 9

Chemical Properties

• Melting Point: 180 °C(dec.)
• Appearance: /
• Storage Temp.: 2-8°C
• Water Solubility: Soluble in water
• CAS DataBase Reference: 1,4-Diazabicyclo[2.2.2]octane-1,4-diium-1,4-disulfinate(CAS DataBase Reference)
• NIST Chemistry Reference: 1,4-Diazabicyclo[2.2.2]octane-1,4-diium-1,4-disulfinate(119752-83-9)
• EPA Substance Registry System: 1,4-Diazabicyclo[2.2.2]octane-1,4-diium-1,4-disulfinate(119752-83-9)

Safety Data

• Hazard Codes: F,Xn
• Statements: 11-22-36/37/38-52/53
• Safety Statements: 26-60
• RIDADR: UN1325 - class 4.1 - PG 2 - Flammable solids, organic, n.o.s., H
• WGK Germany: 3
• Hazardous Substances Data: 119752-83-9(Hazardous Substances Data)

Usage

Uses

1,4-Diazabicyclo[2.2.2]octane bis(sulfur dioxide) (DABSO) is a charge transfer complex that can be used as a sulfur dioxide surrogate:In palladium-catalyzed aminosulfonylation process.In reaction with aryl bromides to synthesize sodium aryl sulfinates.It can also be used to activate DMSO and o-vinylanilines for the synthesis of N-aryl-1H-benzo[d]imidazol-1-amine and 4-aryl quinolines, respectively.

Upstream product

• 280-57-9 1,4-diaza-bicyclo[2.2.2]octane 

Downstream Products

• 3112-88-7 Benzyl phenyl sulfone 
• 640723-20-2 fluorosulfonyl fluoride 
• 368-91-2 4-methoxybenzene-1-sulfonyl fluoride 

Relevant articles and documents

A Convenient Multigram Synthesis of DABSO Using Sodium Sulfite as SO2 Source

A convenient synthesis of DABCO·(SO2)2 (abbreviated as DABSO) is reported. Using a two-chamber setup, sulfur dioxide is generated in one chamber and consumed in the other. This closed system overcomes safety issues related to working

Palladium-catalyzed annulation of 2-(aryldiazenyl) aniline with dimethyl sulfoxide to access N-aryl-1H-benzo[d]imidazol-1-amine

A palladium-catalyzed annulation of 2-(aryldiazenyl) aniline and dimethyl sulfoxide was developed to access N-aryl-1H-benzo[d]imidazol-1-amine in moderate to good yields. Activated by 1,4-diazabicyclo[2.2.2]octane bis(sulfur dioxide) adduct (DABSO), DMSO served as a “[dbnd]CH[sbnd]” fragment during this procedure. It represents a facile pathway leading to benzimidazoles.

Stoichiometric release of SO2 from adducts: Application to the direct synthesis of protected dienes

Abstract The in situ, stoichiometric release of SO2 was studied from DABSO (DABCO adduct with SO2) and DMAP adduct. When involved in cheletropic additions, free SO2 released by this technique proved much more reactive than its adducts. Some examples of applications towards the direct synthesis of protected dienes from allylic alcohols are given.