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742937

Sigma-Aldrich

1,4-Diazabicyclo[2.2.2]octan-bis-(schwefeldioxid)-Addukt

≥95% (sulfur, elemental analysis)

Synonym(e):

DABSO

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About This Item

Empirische Formel (Hill-System):
C6H12N2O4S2
CAS-Nummer:
119752-83-9
Molekulargewicht:
240.30
MDL-Nummer:
MFCD22377802
UNSPSC-Code:
12352005
PubChem Substanz-ID:
329765601
NACRES:
NA.22

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Qualitätsniveau

100

Assay

≥95% (sulfur, elemental analysis)

Form

powder

Zusammensetzung

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

Lagertemp.

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

InChIKey

RWISEVUOFYXWFO-UHFFFAOYSA-N

Anwendung

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]

Piktogramme

FlameExclamation mark
GHS02,GHS07

Signalwort

Danger

Gefahreneinstufungen

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

Zielorgane

Respiratory system

Lagerklassenschlüssel

4.1B - Flammable solid hazardous materials

WGK

WGK 3

Flammpunkt (°F)

Not applicable

Flammpunkt (°C)

Not applicable

Hier finden Sie alle aktuellen Versionen:

Analysenzertifikate (COA)

Lot/Batch Number
BCCK0148
BCBV9999
BCBM7813V
BCBP1068V
BCBN6615V

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

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)
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)
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Verwandter Inhalt

Willis Group – Professor Product Portal

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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      For all products, we recommend handling per defined conditions as printed in our product literature and website product descriptions. We recommend that products should be routinely inspected by customers to ensure they perform as expected.
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      For more information, please refer to the Product Dating Information document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/449/386/product-dating-information-mk.pdf

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  2. How is shipping temperature determined? And how is it related to the product storage temperature?

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    1. Products may be shipped at a different temperature than the recommended long-term storage temperature. If the product quality is sensitive to short-term exposure to conditions other than the recommended long-term storage, it will be shipped on wet or dry-ice. If the product quality is NOT affected by short-term exposure to conditions other than the recommended long-term storage, it will be shipped at ambient temperature. As shipping routes are configured for minimum transit times, shipping at ambient temperature helps control shipping costs for our customers. For more information, please refer to the Storage and Transport Conditions document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/316/622/storage-transport-conditions-mk.pdf

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