347116
Samarium(II) iodide solution
0.1 M in THF, contains samarium chips as stabilizer
Synonym(s):
Samarium diiodide
About This Item
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form
liquid
Quality Level
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
SMILES string
I[Sm]I
InChI
1S/2HI.Sm/h2*1H;/q;;+2/p-2
InChI key
UAWABSHMGXMCRK-UHFFFAOYSA-L
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Related Categories
Application
- Benzannulated pyrrolizidines and indolizidines by SmI2-induced cyclizations of indole derivatives.
- Chiral 4-substituted 2-oxazolidinones and 5,5-disubstituted oxazolidinones through asymmetric Reformatsky type reaction.
- γ-Aminoalkyl substituted γ-butyrolactones via ketyl-alkene coupling reaction.
It can also be used in:
- Reduction of conjugated double and triple bonds into alkenes using SmI2/H2O/amine mixtures.
- Conversion of β-hydroxyketones into 1,3-diols by SmI2/H2O/Et3N.
- Selective reduction of 6-membered lactones to the corresponding diols/triols using SmI2-H2O reagent system.
SmI2 is an effective single-electron reducing agent for the promotion of ketone-olefin, ketyl aryl cyclizations, and pinacol coupling reactions under mild conditions. Often both intramolecular and intermolecular couplings proceed in a highly stereoselective fashion. It is also used in the synthesis of new heteroleptic samarium aryloxide/cyclopentadienide complexes.
Packaging
Legal Information
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Danger
Hazard Classifications
Carc. 2 - Eye Irrit. 2 - Flam. Liq. 2 - Water-react 3
supp_hazards
Storage Class
4.3 - Hazardous materials, which set free flammable gases upon contact with water
wgk_germany
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
Certificates of Analysis (COA)
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