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Merck

347116

Sigma-Aldrich

Samarium(II) iodide solution

0.1 M in THF, contains samarium chips as stabilizer

Sinónimos:

Samarium diiodide

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About This Item

Fórmula lineal:
SmI2
Número de CAS:
Peso molecular:
404.17
MDL number:
UNSPSC Code:
12352302
PubChem Substance ID:
NACRES:
NA.22

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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Application

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.

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

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_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


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Visite la Librería de documentos

The Journal of Organic Chemistry, 59, 6900-6900 (1994)
Reduction of β-Hydroxyketones by SmI2/H2O/Et3N
Davis TA, et al.
Organic Letters, 7(1), 119-122 (2005)
Tetrahedron, 59, 10351-10351 (2003)
One-Step Highly Diastereoselective Synthesis of γ-Aminoalkyl-Substituted γ-Butyrolactones by an Asymmetric Samarium-Mediated Ketyl-Alkene Coupling Reaction
Fukuzawa S-I, et al.
The Journal of Organic Chemistry, 68(5), 2042-2044 (2003)
Novel stereoselective syntheses of highly functionalized benzannulated pyrrolizidines and indolizidines by samarium diiodide induced cyclizations of indole derivatives
Gross S and Reissig H-U
Organic Letters, 5(23), 4305-4307 (2003)

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