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347116

Sigma-Aldrich

Samarium(II) iodide solution

0.1 M in THF, contains samarium chips as stabilizer

Synonyme(s) :

Samarium diiodide

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About This Item

Formule linéaire :
SmI2
Numéro CAS:
32248-43-4
Poids moléculaire :
404.17
Numéro MDL:
MFCD00058873
Code UNSPSC :
12352302
ID de substance PubChem :
24861467
Nomenclature NACRES :
NA.22

Forme

liquid

Niveau de qualité

200

Contient

samarium chips as stabilizer

Pertinence de la réaction

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

Concentration

0.1 M in THF

Densité

0.922 g/mL at 25 °C

Température de stockage

2-8°C

Chaîne SMILES 

I[Sm]I

InChI

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

Clé InChI

UAWABSHMGXMCRK-UHFFFAOYSA-L

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Catégories apparentées

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.

Conditionnement

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

Informations légales

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

Pictogrammes

FlameHealth hazardExclamation mark
GHS02,GHS08,GHS07

Mention d'avertissement

Danger

Classification des risques

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

Organes cibles

Central nervous system, Respiratory system

Risques supp

EUH019

Code de la classe de stockage

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

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

-2.2 °F - closed cup - Solvent

Point d'éclair (°C)

-19 °C - closed cup - Solvent

Équipement de protection individuelle

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

Certificats d'analyse (COA)

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Consulter la Bibliothèque de documents

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)
Tetrahedron, 59, 10351-10351 (2003)
Reduction of β-Hydroxyketones by SmI2/H2O/Et3N
Davis TA, et al.
Organic Letters, 7(1), 119-122 (2005)
Samarium(II) Iodide Promoted Intermolecular Ketone-Olefin Couplings Chelation-Controlled by .alpha.-Hydroxyl Groups
Motoi Kawatsura FM and Haruhisa Shirahama
The Journal of Organic Chemistry, 59, 6900-6900 (1994)
Zhaomin Hou et al.
Inorganic chemistry, 35(25), 7190-7195 (1996-12-04)
Synthesis of a new class of heteroleptic samarium aryloxide complexes has been achieved by the use of homoleptic samarium(II) bis(aryloxide) Sm(OAr)(2)(THF)(3) (1, Ar = C(6)H(2)Bu(t)(2)-2,6-Me-4) as a starting material, which is easily obtained by reaction of Sm(N(SiMe(3))(2))(2)(THF)(2) with 2 equiv
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