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CAS RN: 119752-83-9 | Product Number: B3960

Bis(sulfur Dioxide)-1,4-diazabicyclo[2.2.2]octane Adduct


Purity: >94.0%(T)
Synonyms:
  • DABCO-Bis(sulfur Dioxide)
  • DABSO
Product Documents:
1G
A$112.00
≥40  1  
5G
A$365.00
32   ≥40 
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* ChemSupply Australia Pty Ltd (Phone: 08-8440-2000 / email:  sales@chemsupply.com.au)

Product Number B3960
Purity / Analysis Method >94.0%(T)
Molecular Formula / Molecular Weight C__6H__1__2N__2O__4S__2 = 240.29 
Physical State (20 deg.C) Solid
Storage Temperature Refrigerated (0-10°C)
Store Under Inert Gas Store under inert gas
Condition to Avoid Air Sensitive,Heat Sensitive
Packaging and Container 1G-Glass Bottle with Plastic Insert (View image)
CAS RN 119752-83-9
Reaxys Registry Number 21034099
PubChem Substance ID 354335121
Specifications
Appearance White to Almost white powder to crystal
Purity(Iodometric back titration) min. 94.0 %
Properties (reference)
Melting Point 180 °C(dec.)
Solubility in water Soluble
GHS
Pictogram Pictogram
Signal Word Warning
Hazard Statements H315 : Causes skin irritation.
H319 : Causes serious eye irritation.
Precautionary Statements P264 : Wash skin thoroughly after handling.
P280 : Wear protective gloves/ eye protection/ face protection.
P302 + P352 : IF ON SKIN: Wash with plenty of water.
P337 + P313 : If eye irritation persists: Get medical advice/ attention.
P305 + P351 + P338 : IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.
P362 + P364 : Take off contaminated clothing and wash it before reuse.
P332 + P313 : If skin irritation occurs: Get medical advice/ attention.
Related Laws:
Transport Information:
H.S.code* 2933.59-000
*This code is applied to the products when TCI exports from Japan and not for import in your country.
Application
TCI Practical Example: Nickel(II)-Catalyzed One Pot Synthesis of Sulfones from Aryl Boronic Acid and DABSO

ニッケル触媒による芳香族ボロン酸とDABSOを用いたるワンポットスルホン合成

Used Chemicals

Procedure

Under nitrogen atmosphere, a degassed DMI (20 mL) solution of 4-biphenylboronic acid (792 mg, 4.00 mmol), DABSO (577 mg, 2.40 mmol), tmphen (95 mg, 0.40 mmol), lithium tert-butoxide (320 mg, 4.00 mmol) and NiBr2(glyme) (123 mg, 0.40 mmol) was stirred at 100 °C for 14 hours. The mixture was cooled to room temperature and tert-butyl bromoacetate (1.17 mL, 8.00 mmol) was added and the reaction mixture stirred for 1 hour. Water (20 mL) was poured into the reaction mixture and the mixture was extracted with diethyl ether (50 mL x 3). The combined organic phase was washed with water (50 mL) and brine (40 mL), dried over sodium sulfate and filtered. The solvent was removed under reduced pressure and the residue was purified by medium pressure preparative chromatography (ethyl acetate:hexane = 5:95 - 15:85 on silica gel) to give compound 1 as a white solid (1.01 g, 76%).

Experimenter’s Comments

NiBr2(glyme) and LiOtBu were weighed into a sample tube in a glove box because these reagents are moisture sensitive. If these were used in air, it should be weighted quickly and used up the reagents as soon as possible after opening.
Since the ligand of NiBr2(glyme) may be desorbed under reduced pressure, depressurization operations is desirable to be finished as soon as possible.
The reaction mixture was monitored by TLC (ethyl acetate:hexane = 2:1, Rf = 0.38) and UPLC-MS.

Analytical Data

Compound 1

1H NMR (400 MHz, CDCl3); δ 8.00 (d, 2H, J = 8.9 Hz), 7.78 (m, 2H), 7.58–7.66 (m, 2H), 7.42-7.54 (m, 3H), 4.08 (s, 2H), 1.58 (s, 2H), 1.39 (s, 9H).

Lead Reference


Application
TCI Practical Example: One-Pot Palladium-Catalyzed Fluorosulfonylation of an Aryl Bromide Using DABSO and NFSI

パラジウム触媒によるDABSOとNFSIを用いたアリールブロミドのワンポットフッ化スルホニル化

Used Chemicals

Procedure

To a solution of 4-bromobiphenyl (1.17 g, 5.00 mmol), DABSO (721 mg, 3.00 mmol), and PdCl2(Amphos)2 (177 mg, 0.25 mmol) in anhydrous isopropyl alcohol (20 mL) was added triethylamine (2.1 mL, 15 mmol) at room temperature and the mixture was stirred at 75 °C for 23 hours. The suspension was cooled at room temperature and NFSI (2.36 g, 7.5 mmol) was added and the reaction mixture stirred for 3 hours until completion. The solvent was removed under reduced pressure. The residue was diluted with ethyl acetate (20 mL) and filtrated through celite pad. The filtrate was washed with saturated aqueous Na2S2O3 solution (20 mL) and brine (20 mL), dried over sodium sulfate and filtered. The solvent was removed under reduced pressure and the residue was purified by medium pressure preparative chromatography (ethyl acetate:hexane = 2:98 - 5:95 on silica gel) to give compound 1 as a white solid (928 mg, 79%).

Experimenter’s Comments

The reaction mixture was monitored by TLC (ethyl acetate:hexane = 1:9, Rf = 0.57) and UPLC-MS.

Analytical Data

Compound 1

1H NMR (400 MHz, CDCl3); δ 8.12–8.04 (m, 2H), 7.86–7.80 (m, 2H), 7.67–7.58 (m, 2H), 7.44-7.55 (m, 3H).

Lead Reference


Application
DABSO as a SO2 Source Usable for Direct Sulfonylative-Suzuki Coupling of Aryl Boronic Acids

Reference


Application
Direct Synthesis of Sulfonamide derivatives using DABSO

Reference


Application
Direct Synthesis of Sulfones using DABSO and TBAT

Reference


PubMed Literature


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