CAS 32248-43-4 Samarium(II) iodide - Catalysts / Alfa Chemistry

Synonyms

SAMARIUM(II) IODIDE;SAMARIUM IODIDE;SAMARIUM(II) IODIDE SOLUTION, STAB., ~0. 1 M IN THF;SAMARIUM(II) IODIDE, 0.1M SOLUTION IN TE TRAHYDROFURAN;SAMARIUM(II) IODIDE, POWDER, 99.9+%;SAMARIUM (II) IODIDE 0.1M IN THF;0.1MinTHF,stabilized;Samarium(II)iodide,0.1

IUPAC Name

samarium;diiodide

Molecular Weight

404.17 g/mol

Molecular Formula

SmI2

Canonical SMILES

[I-].[I-].[Sm]

InChI

InChI=1S/2HI.Sm/h2*1H;/p-2

InChI Key

IXYRYFKRXLLFRG-UHFFFAOYSA-L

Density

0.922g/mL

Storage

2~8°C, inflammable area

Complexity

Covalently-Bonded Unit Count

Exact Mass

405.72868g/mol

Formal Charge

-2

H-Bond Acceptor

H-Bond Donor

Heavy Atom Count

Monoisotopic Mass

405.72868g/mol

Rotatable Bond Count

UNII

L15T8U41LC

Application

Samarium(II) iodide, known as "Kagan's reagent," is a powerful single-electron reducing agent used in organic synthesis. This green solid forms from the high-temperature decomposition of samarium(III) iodide and remains green in solution. Its primary purpose is to facilitate various complex chemical transformations due to its substantial reduction potential. SmI2 is used in synthesizing benzannulated pyrrolizidines and indolizidines via cyclizations of indole derivatives, and in forming chiral 4-substituted 2-oxazolidinones through asymmetric Reformatsky-type reactions. Additionally, it aids in creating γ-aminoalkyl substituted γ-butyrolactones via ketyl-alkene coupling. This reagent also enables the reduction of conjugated double and triple bonds to alkenes, the conversion of β-hydroxyketones into 1,3-diols, and the selective reduction of six-membered lactones to their corresponding diols/triols. SmI2 is particularly effective in promoting ketone-olefin and ketyl aryl cyclizations, alongside pinacol coupling reactions, often yielding highly stereoselective intramolecular and intermolecular couplings. It is also involved in the synthesis of new heteroleptic samarium aryloxide/cyclopentadienide complexes, making it a versatile tool in electron transfer reactions and organic synthesis.

January 3, 2025

Excellent Reagent for Organic Synthesis

Samarium(II) iodide from Alfa Chemistry is exceptional for organic synthesis in our lab. Its effectiveness in stereoselective couplings and unique reduction reactions enhanced our research outcomes substantially. Highly recommend for efficient electron transfer processes.