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347116

Sigma-Aldrich

Samarium(II) iodide solution

0.1 M in THF, contains samarium chips as stabilizer

Sinonimo/i:

Samarium diiodide

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About This Item

Formula condensata:
SmI2
Numero CAS:
32248-43-4
Peso molecolare:
404.17
Numero MDL:
MFCD00058873
Codice UNSPSC:
12352302
ID PubChem:
24861467
NACRES:
NA.22

Forma fisica

liquid

Livello qualitativo

200

contiene

samarium chips as stabilizer

Impiego in reazioni chimiche

core: samarium
reagent type: catalyst
reaction type: Reductions
reagent type: reductant

Concentrazione

0.1 M in THF

Densità

0.922 g/mL at 25 °C

Temperatura di conservazione

2-8°C

Stringa SMILE

I[Sm]I

InChI

1S/2HI.Sm/h2*1H;/q;;+2/p-2
UAWABSHMGXMCRK-UHFFFAOYSA-L

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Categorie correlate

Applicazioni

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.

Confezionamento

The 25 mL Sure/Seal™ bottle is recommended as a single-use bottle. Repeated punctures will likely result in decreased performance of product.

Note legali

Sure/Seal is a trademark of Sigma-Aldrich Co. LLC

Avvertenze

Danger

Indicazioni di pericolo

H225,H261,H319,H335,H336,H351

Classi di pericolo

Carc. 2 - Eye Irrit. 2 - Flam. Liq. 2 - STOT SE 3 - Water-react 3

Organi bersaglio

Central nervous system, Respiratory system

Rischi supp

EUH019

Codice della classe di stoccaggio

4.3 - Hazardous materials which set free flammable gases upon contact with water

Classe di pericolosità dell'acqua (WGK)

WGK 3

Punto d’infiammabilità (°F)

-2.2 °F - closed cup - Solvent

Punto d’infiammabilità (°C)

-19 °C - closed cup - Solvent

Dispositivi di protezione individuale

Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter

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Certificati d'analisi (COA)

Lot/Batch Number
SHBP2660
SHBP2662
SHBM3788
SHBN0334
SHBN0346

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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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