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Sigma-Aldrich

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

≥95% (sulfur, elemental analysis)

Sinonimo/i:

DABCO•(SO2)2, DABSO

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52,20 €
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1 G
52,20 €
5 G
196,00 €

About This Item

Formula empirica (notazione di Hill):
C6H12N2O4S2
Numero CAS:
119752-83-9
Peso molecolare:
240.30
Numero MDL:
MFCD22377802
Codice UNSPSC:
12352005
ID PubChem:
329765601
NACRES:
NA.22

52,20 €

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Saggio

≥95% (sulfur, elemental analysis)

Stato

powder

Composizione

active SO2, ~50%
carbon, 28.3-31.6%

Temperatura di conservazione

2-8°C

Stringa SMILE

[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
RWISEVUOFYXWFO-UHFFFAOYSA-N

Applicazioni

1,4-Diazabicyclo[2.2.2]octane bis(sulfur dioxide) (DABSO) is a charge transfer complex[1] that can be used as a sulfur dioxide surrogate:
  • In palladium-catalyzed aminosulfonylation process.[2]
  • In reaction with aryl bromides to synthesize sodium aryl sulfinates.[3]

It can also be used to activate DMSO and o-vinylanilines for the synthesis of N-aryl-1H-benzo[d]imidazol-1-amine[4] and 4-aryl quinolines, respectively.[5]

Pittogrammi

FlameExclamation mark
GHS02,GHS07

Avvertenze

Danger

Indicazioni di pericolo

H228,H302,H315,H319,H335,H412

Classi di pericolo

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

Organi bersaglio

Respiratory system

Codice della classe di stoccaggio

4.1B - Flammable solid hazardous materials

Classe di pericolosità dell'acqua (WGK)

WGK 3

Punto d’infiammabilità (°F)

Not applicable

Punto d’infiammabilità (°C)

Not applicable

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Certificati d'analisi (COA)

Lot/Batch Number
BCCK0148
BCBV9999
BCBM7813V
BCBP1068V
BCBN6615V

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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
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)
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)
DABCO-bis (sulfur dioxide), DABSO, as a convenient source of sulfur dioxide for organic synthesis: utility in sulfonamide and sulfamide preparation.
Woolven H, et al.
Organic Letters, 13(18), 4876-4878 (2011)
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Contenuto correlato

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Research in the Willis group is focused on the development of new catalysts and reactions for synthetic chemistry. The group is particularly interested in addressing synthetic challenges that are applicable to the pharmaceutical and agrochemical industries.

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