Name: SAMARIUM(II) IODIDE 0.1M SOLUTION IN TETRAHYDROFURAN (C005B-032469)
SKU: C005B-032469
Availability: OutOfStock

SAMARIUM(II) IODIDE 0.1M SOLUTION IN TETRAHYDROFURAN (C005B-032469)

Catalog No.

C005B-032469

Manufacturer No.

347116-100ML

Manufacturer Name

Sigma-Aldrich

Quantity

100

Unit of Measure

Application Samarium(II) iodide solution (SmI 2 ) can be used as a reagent in the synthesis of: Benzannulated pyrrolizidines and indolizidines by SmI 2 -induced cyclizations of indole derivatives. Chiral 4-substituted 2-oxazolidinones and

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Description
Specifications

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

Molecular Weight: 404.17. Empirical Formula: I₂Sm. linearFormula: SmI₂. form: liquid. Quality Level: 200. 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 . Â°C. storage temp.: 2-8Â°C. SMILES string: I[Sm]I. InChI: 1S/2HI.Sm/h2*1H. /q. . +2/p-2. InChI key: UAWABSHMGXMCRK-UHFFFAOYSA-L. Pictograms: GHS02,GHS07,GHS08. Signal Word: Danger. Hazard Statements: H225 - H319 - H335 - H351 - H373. Precautionary Statements: P201 - P210 - P233 - P260 - P280 - P304 + P340 + P312. Hazard Classifications: Carc. 2 - Eye Irrit. 2 - Flam. Liq. 2 - STOT RE 2 - STOT SE 3. Target Organs: Respiratory system. Supp Hazards: EUH018 - EUH019. Storage Class Code: 3 - Flammable liquids. WGK: WGK 3. Flash Point(F): -2.2 Â°F - closed cup - Solvent. Flash Point(C): -19 Â°C - closed cup - Solvent. Personal Protective Equipment: Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter.