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For all products, we recommend handling per defined conditions as printed in our product literature and website product descriptions. We recommend that products should be routinely inspected by customers to ensure they perform as expected.
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For more information, please refer to the Product Dating Information document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/418/501/product-dating-information-06-25-mk.pdf
347116
Samarium(II)-iodid -Lösung
0.1 M in THF, contains samarium chips as stabilizer
Synonym(e):
Samarium(II)-iodid
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Produktname
Samarium(II)-iodid -Lösung, 0.1 M in THF, contains samarium chips as stabilizer
InChI
1S/2HI.Sm/h2*1H;/q;;+2/p-2
SMILES string
I[Sm]I
InChI key
UAWABSHMGXMCRK-UHFFFAOYSA-L
form
liquid
contains
samarium chips as stabilizer
reaction suitability
core: samarium
reagent type: catalyst
reaction type: Reductions
reagent type: reductant
concentration
0.1 M in THF
density
0.922 g/mL at 25 °C
storage temp.
2-8°C
Quality Level
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Dieser Artikel | 409340 | 547980 | 464678 |
|---|---|---|---|
| reaction suitability core: samarium, reagent type: reductant, reagent type: catalyst | reaction suitability - | reaction suitability core: samarium, reagent type: catalyst | reaction suitability - |
| form liquid | form powder | form solid | form powder |
| Quality Level 200 | Quality Level 100 | Quality Level 100 | Quality Level 100 |
| storage temp. 2-8°C | storage temp. - | storage temp. - | storage temp. - |
| density 0.922 g/mL at 25 °C | density - | density - | density 6.003 g/mL at 25 °C (lit.) |
| contains samarium chips as stabilizer | contains - | contains - | contains - |
Application
- Benzannulierte Pyrrolizidinalkaloide und Indolizidine mittels SmI2-induzierten Zyklisierungen von Indol-Derivaten[1]
- Chirale 4-substituierte 2-Oxazolidinone und 5,5-disubstituierte Oxazolidinone mittels asymmetrischer Reaktion nach Reformatsky[2]
- γ-Aminoalkyl-substituierte γ-Butyrolactone mittels Ketyl-Alken-Kopplungsreaktion.[3]
Es kann ferner wie folgt eingesetzt werden:
- Reduktion von konjugierten Doppel- und Dreifachbindungen zu Alkenen unter Verwendung von SmI2-/H2O-/Amin-Mischungen[4]
- Umwandlung von β-Hydroxyketonen in 1,3-Diole mittels SmI2/H2O/Et3N[5]
- Selektive Reduktion von 6-gliedrigen Lactonen zu den entsprechenden Diolen/Triolen unter Verwendung eines SmI2-H2O-Reagenzsystems[6]
SmI2 ist ein wirkungsvolles Ein-Elektron-Reduktionsmittel, das die Keton-Olefin- und Pinakol-Kupplungsreaktionen sowie Ketyl-Aryl-Zyklisierungen unter milden Bedingungen begünstigt.[7][8][9] Häufig verlaufen intramolekulare[10] wie intermolekulare[10] Kupplungen in stark stereoselektiver Weise. Es wird auch bei der Synthese von neuen heteroleptischen Samarium-Aryloxid/Cyclopentadienid-Komplexen verwendet.[11][12]
Packaging
Legal Information
supp_hazards
signalword
Danger
Hazard Classifications
Carc. 2 - Eye Irrit. 2 - Flam. Liq. 2 - STOT SE 3 - Water-react 3
target_organs
Central nervous system, Respiratory system
Lagerklasse
4.3 - Hazardous materials which set free flammable gases upon contact with water
wgk
WGK 3
flash_point_f
-2.2 °F - closed cup - Solvent
flash_point_c
-19 °C - closed cup - Solvent
ppe
Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter
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How can I determine the shelf life / expiration / retest date of this product?
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How is shipping temperature determined? And how is it related to the product storage temperature?
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Products may be shipped at a different temperature than the recommended long-term storage temperature. If the product quality is sensitive to short-term exposure to conditions other than the recommended long-term storage, it will be shipped on wet or dry-ice. If the product quality is NOT affected by short-term exposure to conditions other than the recommended long-term storage, it will be shipped at ambient temperature. As shipping routes are configured for minimum transit times, shipping at ambient temperature helps control shipping costs for our customers. For more information, please refer to the Storage and Transport Conditions document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/316/622/storage-transport-conditions-mk.pdf
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