347116
Samarium(II) iodide solution
0.1 M in THF, contains samarium chips as stabilizer
Synonym(s):
Samarium diiodide
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About This Item
Linear Formula:
SmI2
CAS Number:
Molecular Weight:
404.17
NACRES:
NA.22
PubChem Substance ID:
UNSPSC Code:
12352302
MDL number:
form
liquid
Quality Segment
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
Application
Samarium(II) iodide solution (SmI2) can be used as a reagent in the synthesis of:
It can also be used in:
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.
- 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
The 25 mL Sure/Seal™ bottle is recommended as a single-use bottle. Repeated punctures will likely result in decreased performance of product.
Legal Information
Sure/Seal is a trademark of Sigma-Aldrich Co. LLC
signalword
Danger
target_organs
Central nervous system, Respiratory system
supp_hazards
Storage Class
4.3 - Hazardous materials which set free flammable gases upon contact with water
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
Hazard Classifications
Carc. 2 - Eye Dam. 1 - Flam. Liq. 2 - STOT SE 3 - Water-react. 3
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