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742937

Sigma-Aldrich

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

≥95% (sulfur, elemental analysis)

Synonym(s):

DABCO•(SO2)2, DABSO

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About This Item

Empirical Formula (Hill Notation):
C6H12N2O4S2
CAS Number:
119752-83-9
Molecular Weight:
240.30
MDL number:
MFCD22377802
UNSPSC Code:
12352005
PubChem Substance ID:
329765601
NACRES:
NA.22

Quality Level

100

Assay

≥95% (sulfur, elemental analysis)

form

powder

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

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.

Pictograms

FlameExclamation mark
GHS02,GHS07

Signal Word

Danger

Hazard Classifications

Acute Tox. 4 Oral - Aquatic Chronic 3 - Eye Irrit. 2 - Flam. Sol. 1 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

4.1B - Flammable solid hazardous materials

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificates of Analysis (COA)

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Sigma-Aldrich

Sigma-Aldrich

F6937

Fluoroshield™ with 1,4-Diazabicyclo[2.2.2]octane

Palladium-catalyzed aminosulfonylation of aryl halides.
Nguyen B, et al.
Journal of the American Chemical Society, 132(46), 16372-16373 (2010)
Bao Nguyen et al.
Journal of the American Chemical Society, 132(46), 16372-16373 (2010-10-30)
The palladium-catalyzed three-component coupling of aryl iodides, sulfur dioxide, and hydrazines to deliver aryl N-aminosulfonamides is described. The colorless crystalline solid DABCO·(SO(2))(2) was used as a convenient source of sulfur dioxide. The reaction tolerates significant variation of both the aryl
Palladium-catalyzed annulation of 2-(aryldiazenyl) aniline with dimethyl sulfoxide to access N-aryl-1H-benzo [d] imidazol-1-amine.
Wang H, et al.
Tetrahedron Letters, 58(40), 3875-3878 (2017)
Synthesis of sodium aryl sulfinates from aryl bromides employing 1, 4-diazabicyclo [2.2. 2] octane bis (sulfur dioxide) adduct (DABSO) as a bench-stable, gas-free alternative to SO2.
Skillinghaug B, et al.
Tetrahedron Letters, 57(5), 533-536 (2016)
Carbon annulation of ortho-vinylanilines with dimethyl sulfoxide to access 4-aryl quinolines.
Yuan J, et al.
Organic & Biomolecular Chemistry, 15(6), 1334-1337 (2017)
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