347116

Samarium(II) iodide solution

0.1 M in THF, contains samarium chips as stabilizer

• Synonyme(s) : Samarium diiodide
• 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

Propriétés

• 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

Description

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.[1]
• Chiral 4-substituted 2-oxazolidinones and 5,5-disubstituted oxazolidinones through asymmetric Reformatsky type reaction.[2]
• γ-Aminoalkyl substituted γ-butyrolactones via ketyl-alkene coupling reaction.[3]

It can also be used in:

• Reduction of conjugated double and triple bonds into alkenes using SmI₂/H₂O/amine mixtures.[4]
• Conversion of β-hydroxyketones into 1,3-diols by SmI₂/H₂O/Et₃N.[5]
• Selective reduction of 6-membered lactones to the corresponding diols/triols using SmI₂-H₂O reagent system.[6]

SmI₂ is an effective single-electron reducing agent for the promotion of ketone-olefin, ketyl aryl cyclizations, and pinacol coupling reactions under mild conditions.[7][8][9] Often both intramolecular[10] and intermolecular[10] couplings proceed in a highly stereoselective fashion. It is also used in the synthesis of new heteroleptic samarium aryloxide/cyclopentadienide complexes.[11][12]

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

Informations sur la sécurité

• Pictogrammes: GHS02,GHS08,GHS07
• Mention d'avertissement: Danger
• Mentions de danger: H225,H261,H319,H335,H336,H351
• Conseils de prudence: P202 - P210 - P231 + P232 - P233 - P305 + P351 + P338 - P308 + P313
• 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