1,4-Diazabicyclo[2.2.2]octane-1,4-diium-1,4-disulfinate

Base Information

• Chemical Name: 1,4-Diazabicyclo[2.2.2]octane-1,4-diium-1,4-disulfinate
• CAS No.: 119752-83-9
• Molecular Formula: C6H12N2O4S2
• Molecular Weight: 240.304
• Hs Code.: 2933990090
• Mol file: 119752-83-9.mol

Synonyms:1,4-Diazabicyclo[2.2.2]octane-1,4-diium-1,4-disulfinate;1,4-Diazabicyclo[2.2.2]octane bis(sulfur dioxide) adduct;1,4-Diazabicyclo[2.2.2]octane bis(sulfur dioxide) adduct >=95% (sulfur, eleMental analysis);DABSO;1,4-Diazoniabicyclo[2.2.2]octane-1,4-disulphinate;1,4-Diazoniabicyclo[2.2.2]octane-1,4-disulfinate

Chemical Property of 1,4-Diazabicyclo[2.2.2]octane-1,4-diium-1,4-disulfinate

Chemical Property:

• Melting Point: 180 °C(dec.)
• PSA: 157.18000
• LogP: 0.31460
• Storage Temp.: 2-8°C
• Water Solubility.: Soluble in water

Purity/Quality:

99%, ^*data from raw suppliers

1,4-Diazabicyclo[2.2.2]octane bis(sulfur dioxide) adduct ^*data from reagent suppliers

Safty Information:

• Hazard Codes: F,Xn
• Statements: 11-22-36/37/38-52/53
• Safety Statements: 26-60

MSDS Files:

SDS file from LookChem

Useful:

• General Description: 1,4-Diazabicyclo[2.2.2]octane-1,4-diium-1,4-disulfinate (DABSO) is a stable, bench-stable solid adduct of 1,4-diazabicyclo[2.2.2]octane (DABCO) and sulfur dioxide (SO₂), serving as a convenient and safe SO₂ surrogate in synthetic chemistry. It is widely used to avoid handling gaseous SO₂ directly, mitigating associated safety hazards. 1,4-Diazabicyclo[2.2.2]octane-1,4-diium-1,4-disulfinate is synthesized efficiently using a closed two-chamber system with sodium sulfite as the SO₂ source, ensuring controlled generation and consumption of the gas. DABSO is particularly valuable in reactions such as sulfonamide and sulfonyl derivative formations, where it provides a controlled release of SO₂ under mild conditions. Its stability and ease of preparation make it a practical alternative for SO₂-dependent transformations.

Technology Process of 1,4-Diazabicyclo[2.2.2]octane-1,4-diium-1,4-disulfinate

There total 1 articles about 1,4-Diazabicyclo[2.2.2]octane-1,4-diium-1,4-disulfinate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 100.0%

1,4-diaza-bicyclo[2.2.2]octane (280-57-9,88935-43-7) → 1,4-diazabicyclo [2.2.2] octane-1,4-diium-1,4-disulfinate (119752-83-9)

Guidance literature:

With sulfur dioxide;

DOI:10.1021/ol201957n

Reference yield: 89.0%

bromobenzene (108-86-1,52753-63-6) + 1,4-diazabicyclo [2.2.2] octane-1,4-diium-1,4-disulfinate (119752-83-9) + benzyl bromide (100-39-0) → Benzyl phenyl sulfone (3112-88-7)

Guidance literature:

bromobenzene; 1,4-diazabicyclo [2.2.2] octane-1,4-diium-1,4-disulfinate; With magnesium; lithium chloride; In tetrahydrofuran; at 20 ℃; for 1h; Flow reactor;

benzyl bromide; In tetrahydrofuran; N,N-dimethyl-formamide; at 120 ℃; for 2h; Flow reactor; Inert atmosphere;

DOI:10.1021/acs.orglett.7b01590

Reference yield: 83.0%

1,4-diazabicyclo [2.2.2] octane-1,4-diium-1,4-disulfinate (119752-83-9) + C33H34BF5N2 → C33H34BF5N2O2S

Guidance literature:

In benzene-d6; at 20 ℃; for 0.0333333h;

DOI:10.1002/anie.202106724

upstream raw materials:

1,4-diaza-bicyclo[2.2.2]octane

Downstream raw materials:

Benzyl phenyl sulfone

fluorosulfonyl fluoride

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