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347116 Sigma-Aldrich

Samarium(II) iodide solution

0.1 M in THF, contains samarium chips as stabilizer

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Properties

Related Categories 25mL Sure/Seal Reagents, Catalysis and Inorganic Chemistry, Chemical Synthesis, Essential Chemicals, Materials Science,
Quality Level   200
form   liquid
contains   samarium chips as stabilizer
reaction suitability   reagent type: catalyst
reaction type: Reductions
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

Description

Application

An effective single-electron reducing agent for the promotion of ketone-olefin and pinacol coupling reactions under mild conditions. Often both intramolecular and intermolecular couplings proceed in a highly stereoselective fashion. Starting material for the synthesis of new heteroleptic samarium aryloxide/cyclopentadienide complexes.

Samarium(II) iodide solution (SmI2) can be used as a reagent in the synthesis of:
• 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.

SmI2 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.

Packaging

1 L in Sure/Seal™

25, 4×25, 100 mL in Sure/Seal™

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

Safety & Documentation

Safety Information

Symbol 
Signal word 
Danger
Hazard statements 
Target organs 
Respiratory system
Supplemental Hazard Statements 
EUH018 - EUH019
RIDADR 
UN 2056 3 / PGII
WGK Germany 
WGK 3
Flash Point(F) 
-2.2 °F - closed cup
Flash Point(C) 
-19 °C - closed cup

Documents

Certificate of Analysis (COA)

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Certificate of Origin (COO)

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Protocols & Articles

Articles

The Rare Earth Crisis—The Supply/Demand Situation for 2010–2015

K.A. Gschneidner, Jr. Ames Laboratory, U.S. Department of Energy and Department of Materials Science and Engineering Iowa State University, Ames, Iowa 50011-3020, USA Email: cagey@ameslab.gov
Keywords: Absorption, Automotive, Capillary electrophoresis, Catalysis, Ceramics, Coloring agents, Detection methods, Environmental, Industries, Magnetic resonance imaging, Materials Science, Oxidations, Poisons, Reductions, Scintillation, Semiconductor, Separation, Substitutions

Peer-Reviewed Papers
15

References

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