Bis(sulfur Dioxide)-1,4-diazabicyclo[2.2.2]octane Adduct - ≥95% , CAS No.119752-83-9

CAS: 119752-83-9 Cat. No.: D166360 Molecular Weight: 240.3 EC Number: 802-457-9

GRADE & PURITY ≥95%

Synonyms

1,4(c)\\diazabicyclo[2.2.2]octane(c)\\1,4(c)\\diium(c)\\1,4(c)\\disulfinate | 1,4-Diazabicyclo[2.2.2]octane bis(sulfur dioxide) | SY099324 | EN300-321062 | 1,4-Diazabicyclo[2.2.2]octane-1,4-diium-1,4-disulfinate | AMY34553 | Z2689031572 | 1,4-Diazoniabicy

Storage

Store at 2-8°C,Argon charged

Shipped In

Wet ice

Overview

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

Specifications

Synonyms

1, 4(c)\\diazabicyclo[2.2.2]octane(c)\\1, 4(c)\\diium(c)\\1, 4(c)\\disulfinate | 1, 4-Diazabicyclo[2.2.2]octane bis(sulfur dioxide) | SY099324 | EN300-321062 | 1, 4-Diazabicyclo[2.2.2]octane-1, 4-diium-1, 4-disulfinate | AMY34553 | Z2689031572 | 1, 4-Diazoniabicy

Specifications & Purity

≥95%

Storage

Store at 2-8°C, Argon charged

Shipped In

Wet ice

This product requires cold chain shipping. Ground and other economy services are not available.

Purity

≥95%

Names and Identifiers

• Canonical Smiles: C1C[N+]2(CC[N+]1(CC2)S(=O)[O-])S(=O)[O-]
• IUPAC Name: 1,4-diazoniabicyclo[2.2.2]octane-1,4-disulfinate
• InChIKey: RWISEVUOFYXWFO-UHFFFAOYSA-N
• INCHI: 1S/C6H12N2O4S2/c9-13(10)7-1-2-8(5-3-7,6-4-7)14(11)12/h1-6H2
• Isomeric SMILES: C1C[N+]2(CC[N+]1(CC2)S(=O)[O-])S(=O)[O-]
• WGK Germany: 3
• Molecular Weight: 240.3
• Reaxy-Rn: 21980336
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=21980336&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Organoheterocyclic compounds
    • Class Diazinanes
      • Subclass Piperazines

• Kingdom: Organic compounds
• Superclass: Organoheterocyclic compounds
• Class: Diazinanes
• Subclass: Piperazines
• Intermediate Tree Nodes: Not available
• Direct Parent: N-alkylpiperazines
• Alternative Parents: Azacyclic compounds Organopnictogen compounds Organonitrogen compounds Organic oxides Hydrocarbon derivatives
• Molecular Framework: Aliphatic heteropolycyclic compounds
• Substituents: N-alkylpiperazine - Azacycle - Organic nitrogen compound - Organic oxygen compound - Organopnictogen compound - Organic oxide - Hydrocarbon derivative - Organonitrogen compound - Aliphatic heteropolycyclic compound
• Description: This compound belongs to the class of organic compounds known as n-alkylpiperazines. These are organic compounds containing a piperazine ring where the nitrogen ring atom carries an alkyl group.
• External Descriptors: Not available

Data sources

1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.

DOI: 10.1186/s13321-016-0174-y

Chemical and Physical Properties

• Solubility: Soluble in water
• Sensitivity: air and heat and moisture sensitive
• Melt Point(°C): 180 °C
• Molecular Weight: 240.300 g/mol
• XLogP3: -2.100
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 0
• Exact Mass: 240.024 Da
• Monoisotopic Mass: 240.024 Da
• Topological Polar Surface Area: 119.000 Ų
• Heavy Atom Count: 14
• Formal Charge: 0
• Complexity: 243.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 0
• Undefined Atom Stereocenter Count: 0
• Defined Bond Stereocenter Count: 0
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 0
• Covalently-Bonded Unit Count: 1

References

1. Wei Xiao, Jian-Qiang Chen, Jie Wu.  (2025)  Radical sulfonylation with sulfur dioxide surrogates.  CHEMICAL SOCIETY REVIEWS,      [PMID:40498470] [10.1039/D4CS01312C]