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742937 Sigma-Aldrich

1,4-Diazabicyclo[2.2.2]octane bis(sulfur dioxide) adduct

≥95% (sulfur, elemental analysis)

Synonym: DABCO•(SO2)2, DABSO

  • CAS Number 119752-83-9

  • Empirical Formula (Hill Notation) C6H12N2O4S2

  • Molecular Weight 240.30

  •  MDL number MFCD22377802

  •  PubChem Substance ID 329765601

  •  NACRES NA.22

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Properties

Related Categories C-S Bond Formation, C-X Bond Formation (Non-Halogen), Chemical Synthesis, Reproducibility: Validated Products, Synthetic Reagents,
assay   ≥95% (sulfur, elemental analysis)
composition   active SO2, ~50%
  carbon, 28.3-31.6%
storage temp.   2-8°C
SMILES string   [O-]S(=O)[N+]12CC[N+](CC1)(CC2)S([O-])=O
InChI   1S/C6H12N2O4S2/c9-13(10)7-1-2-8(5-3-7,6-4-7)14(11)12/h1-6H2
InChI key   RWISEVUOFYXWFO-UHFFFAOYSA-N

Description

Application

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.

Safety & Documentation

Safety Information

Symbol 
Signal word 
Danger
Target organs 
Respiratory system
RIDADR 
UN1325 - class 4.1 - PG 2 - Flammable solids, organic, n.o.s., HI: all
WGK Germany 
WGK 3
Flash Point(F) 
Not applicable
Flash Point(C) 
Not applicable

Documents

Certificate of Analysis (COA)

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Protocols & Articles

Articles

Michael Willis - Professor Product Portal

From our library of Articles, Sigma-Aldrich presents Michael Willis - Professor Product Portal
Keywords: Agrochemicals, Catalysis, Coupling reactions, Cross couplings, Industries, Pharmaceutical, transformation

Peer-Reviewed Papers
15

References

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