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CAS RN: 2098851-56-8 | Product Number: U0113
Sulfur Dioxide 1-Methylpyrrolidine Adduct
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Purity: >96.0%(qNMR)
Synonyms:
- TIMSO
Product Documents:
| Size | Unit Price | Belgium | Japan* | Quantity |
Shipping Information
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|---|---|---|---|---|---|
| 5G |
€62.00
|
Contact Us | 24 |
|
|
| 25G |
€198.00
|
Contact Us | 13 |
|
* Stock available in Belgium: Shipment on the same day
* Stock available in Japan: Please check the Shipping Simulation for estimated shipments. (excludes regulated items and dry ice shipments)
| Product Number | U0113 |
Purity / Analysis Method 
|
>96.0%(qNMR) |
| Molecular Formula / Molecular Weight | C__5H__1__1NO__2S = 149.21 |
| Physical State (20 deg.C) | Liquid |
| Storage Temperature
|
Frozen (<0°C) |
| Store Under Inert Gas | Store under inert gas |
| Condition to Avoid | Air Sensitive,Heat Sensitive |
| CAS RN | 2098851-56-8 |
| PubChem Substance ID | 468593081 |
Specifications
| Appearance | Light yellow to Amber to Dark green clear liquid |
| Purity(qNMR) | min. 96.0 % |
| NMR | confirm to structure |
Properties (reference)
GHS
| Pictogram |
|
| Signal Word | Danger |
| Hazard Statements | H315 : Causes skin irritation. H319 : Causes serious eye irritation. H225 : Highly flammable liquid and vapour. |
| Precautionary Statements | P210 : Keep away from heat, hot surfaces, sparks, open flames and other ignition sources. No smoking. P233 : Keep container tightly closed. P264 : Wash skin thoroughly after handling. P280 : Wear protective gloves/ protective clothing/ eye protection/ face protection/ hearing protection. P370 + P378 : In case of fire: Use dry sand, dry chemical or alcohol-resistant foam to extinguish. P303 + P361 + P353 : IF ON SKIN (or hair): Take off immediately all contaminated clothing. Rinse skin with water. |
Related Laws:
Transport Information:
| UN Number | UN1993 |
| Class | 3 |
| Packing Group | II |
| HS Number | 2933998090 |
Application
TCI Practical Example: Direct Synthesis of Lithium Pyridine Sulfinate Using TIMSO
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Used Chemicals
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- 5-Bromo-2-methoxypyridine [B2398]
- Sulfur Dioxide 1-Methylpyrrolidine Adduct (= TIMSO) [U0113]
- Butyllithium (ca. 15% in Hexane, ca. 1.6mol/L)
- THF
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Procedure
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5-Bromo-2-methoxypyridine (1.00 g, 5.32 mmol) in THF (30 mL) was stirred at -78 °C for 5 minutes and butyllithium (ca. 1.6mol/L in hexane, 3.66 mL, 5.85 mmol) was added to the solution and stirred further for 40 minutes at same temperature. Then, TIMSO (1.06 g, 6.38 mmol) was added and stirred at room temperature for 30 minutes. The precipitated solid was collected by filtration and washed with acetone (2 x 20 mL) and diethyl ether (2 x 20 mL) to give 1 as a white solid (895 mg, 94% yield).
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Experimenter’s Comments
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The reaction mixture was monitored by NMR.
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Analytical Data
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Lithium 6-Methoxypyridine-3-sulfinate (1)
1H NMR (270 MHz, D2O); δ 8.09 (d, J = 1.9 Hz, 1H), 7.77 (dd, J = 6.2, 2.2 Hz, 1H), 6.80 (d, J = 8.1 Hz, 1H), 3.77 (s, 3H).
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Lead Reference
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- Pyridine sulfinates as general nucleophilic coupling partners in palladium-catalyzed cross-coupling reactions with aryl halides
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Other Reference
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- Catalyst Selection Facilitates the Use of Heterocyclic Sulfinates as General Nucleophilic Coupling Partners in Palladium-Catalyzed Coupling Reactions
Application
Direct Synthesis of Lithium Pyridinesulfinate using TIMSO
To a solution of 5-bromo-2-methoxypyridine (2.5 mL, 19.3 mmol) in THF (100.0 mL) at -78 °C, n-BuLi (8.2 mL, 2.12 M in hexane, 17.4 mmol, 0.9 equiv.) is added slowly. The mixture is stirred for 40 minutes before U0113 (1.0 equiv.) is added slowly. After complete addition, the solution is allowed to warm to room temperature and the crude product is collected by vacuum filtration and washed with acetone (2 x 20 mL) and Et2O (2 x 20 mL) to yield the lithium pyridinesulfinate (3.4 g, 99%).
References
- Pyridine sulfinates as general nucleophilic coupling partners in palladium-catalyzed cross-coupling reactions with aryl halides
- Catalyst Selection Facilitates the Use of Heterocyclic Sulfinates as General Nucleophilic Coupling Partners in Palladium-Catalyzed Coupling Reactions
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