347116

Samarium(II) iodide solution

0.1 M in THF, contains samarium chips as stabilizer

• Sinónimos: Samarium diiodide
• Fórmula lineal: SmI₂
• Número de CAS: 32248-43-4
• Peso molecular: 404.17
• Número MDL: MFCD00058873
• Código UNSPSC: 12352302
• ID de la sustancia en PubChem: 24861467
• NACRES: NA.22

Propiedades

• Formulario: liquid
• Nivel de calidad: 200
• contiene: samarium chips as stabilizer
• idoneidad de la reacción: core: samarium; reagent type: catalyst; reaction type: Reductions; reagent type: reductant
• concentración: 0.1 M in THF
• densidad: 0.922 g/mL at 25 °C
• temp. de almacenamiento: 2-8°C
• cadena SMILES: I[Sm]I
• InChI: 1S/2HI.Sm/h2*1H;/q;;+2/p-2
• Clave InChI: UAWABSHMGXMCRK-UHFFFAOYSA-L

Descripción

Aplicación

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.

Envase

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

Información legal

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

Información de seguridad

• Pictogramas: GHS02,GHS08,GHS07
• Palabra de señalización: Danger
• Frases de peligro: H225,H261,H319,H335,H336,H351
• Consejos de prudencia: P202 - P210 - P231 + P232 - P233 - P305 + P351 + P338 - P308 + P313
• Clasificaciones de peligro: Carc. 2 - Eye Irrit. 2 - Flam. Liq. 2 - STOT SE 3 - Water-react 3
• Órganos de actuación: Central nervous system, Respiratory system
• Riesgos supl.: EUH019
• Código de clase de almacenamiento: 4.3 - Hazardous materials which set free flammable gases upon contact with water
• Clase de riesgo para el agua (WGK): WGK 3
• Punto de inflamabilidad (°F): -2.2 °F - closed cup - Solvent
• Punto de inflamabilidad (°C): -19 °C - closed cup - Solvent
• Equipo de protección personal: Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter