347116

Samarium(II) iodide solution

0.1 M in THF, contains samarium chips as stabilizer

• Synonym(s): Samarium diiodide
• Linear Formula: SmI₂
• CAS Number: 32248-43-4
• Molecular Weight: 404.17
• MDL number: MFCD00058873
• UNSPSC Code: 12352302
• PubChem Substance ID: 24861467
• NACRES: NA.22

Properties

• 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 °C
• storage temp.: 2-8°C
• SMILES string: I[Sm]I
• InChI: 1S/2HI.Sm/h2*1H;/q;;+2/p-2
• InChI key: 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]

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

Safety Information

• Pictograms: GHS02,GHS08,GHS07
• Signal Word: Danger
• Hazard Statements: H225,H261,H319,H335,H336,H351
• Precautionary Statements: P202 - P210 - P231 + P232 - P233 - P305 + P351 + P338 - P308 + P313
• Hazard Classifications: Carc. 2 - Eye Irrit. 2 - Flam. Liq. 2 - STOT SE 3 - Water-react 3
• Target Organs: Central nervous system, Respiratory system
• Supplementary Hazards: EUH019
• Storage Class Code: 4.3 - Hazardous materials which set free flammable gases upon contact with water
• WGK: WGK 3
• Flash Point(F): -2.2 °F - closed cup - Solvent
• Flash Point(C): -19 °C - closed cup - Solvent
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves