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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 | Philadelphia, PA | Portland, OR | Japan* | Quantity |
Shipping Information
|
|---|---|---|---|---|---|---|
| 5G |
$101.00
|
1 | 1 | 24 |
|
|
| 25G |
$255.00
|
1 | 2 | 12 |
|
* Items in stock locally typically ship the same day of ordering. Items from Japan stock are able to ship from a US warehouse within 2 weeks after ordering. For additional estimated shipment times, please refer to the Shipping Simulation tool. Note: Excludes regulated items and items that ship on ice.
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| 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 vapor. |
| Precautionary Statements | P501 : Dispose of contents/ container to an approved waste disposal plant. P240 : Ground/bond container and receiving equipment. P210 : Keep away from heat/sparks/open flames/hot surfaces. No smoking. P233 : Keep container tightly closed. P243 : Take precautionary measures against static discharge. P241 : Use explosion-proof electrical/ ventilating/ lighting/ equipment. P242 : Use only non-sparking tools. P264 : Wash skin thoroughly after handling. P280 : Wear protective gloves/ eye protection/ face protection. P370 + P378 : In case of fire: Use dry sand, dry chemical or alcohol-resistant foam to extinguish. 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. P303 + P361 + P353 : IF ON SKIN (or hair): Take off immediately all contaminated clothing. Rinse skin with water/shower. P332 + P313 : If skin irritation occurs: Get medical advice/ attention. P362 : Take off contaminated clothing and wash before reuse. P403 + P235 : Store in a well-ventilated place. Keep cool. |
Related Laws:
Transport Information:
| UN Number (DOT-AIR) | UN1993 |
| Class (DOT-AIR) | 3 |
| Packing Group (TCI-A) | II |
| HS Number | 2933.99.9701 |
Application
TCI Practical Example: Direct Synthesis of Lithium Pyridine Sulfinate Using TIMSO
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Used Chemicals
-
- 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
Product Articles
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