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347116
Samarium(II) iodide solution
0.1 M in THF, contains samarium chips as stabilizer
Synonym(s):
Samarium diiodide
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Product Name
Samarium(II) iodide solution, 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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This Item | 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
- Benzannulated pyrrolizidines and indolizidines by SmI2-induced cyclizations of indole derivatives.[1]
- Chiral 4-substituted 2-oxazolidinones and 5,5-disubstituted oxazolidinones through asymmetric Reformatsky type reaction.[2]
- γ-Aminoalkyl substituted γ-butyrolactones via ketyl-alkene coupling reaction.[3]
It can also be used in:
- Reduction of conjugated double and triple bonds into alkenes using SmI2/H2O/amine mixtures.[4]
- Conversion of β-hydroxyketones into 1,3-diols by SmI2/H2O/Et3N.[5]
- Selective reduction of 6-membered lactones to the corresponding diols/triols using SmI2-H2O reagent system.[6]
SmI2 is an effective single-electron reducing agent for the promotion of ketone-olefin, ketyl aryl cyclizations, and pinacol coupling reactions under mild conditions.[7][8][9] Often both intramolecular[10] and intermolecular[10] couplings proceed in a highly stereoselective fashion. It is also used in the synthesis of new heteroleptic samarium aryloxide/cyclopentadienide complexes.[11][12]
Packaging
Legal Information
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
supp_hazards
Storage Class
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 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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