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347116

Sigma-Aldrich

Samarium(II) iodide solution

0.1 M in THF, contains samarium chips as stabilizer

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Synonym(s):
Samarium diiodide
Linear Formula:
SmI2
CAS Number:
Molecular Weight:
404.17
MDL number:
PubChem Substance ID:

form

liquid

Quality Level

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

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This Item
409340547980464678
Samarium(II) iodide solution 0.1 M in THF, contains samarium chips as stabilizer

347116

Samarium(II) iodide solution

Samarium(II) iodide anhydrous, powder, ≥99.9% trace metals basis

409340

Samarium(II) iodide

Palladium(II) iodide 97%

464678

Palladium(II) iodide

form

liquid

form

powder

form

solid

form

powder

Quality Level

200

Quality Level

-

Quality Level

-

Quality Level

-

storage temp.

2-8°C

storage temp.

-

storage temp.

-

storage temp.

-

density

0.922 g/mL at 25 °C

density

-

density

-

density

6.003 g/mL at 25 °C (lit.)

contains

samarium chips as stabilizer

contains

-

contains

-

contains

-

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

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Danger

Hazard Classifications

Carc. 2 - Eye Irrit. 2 - Flam. Liq. 2 - Water-react 3

supp_hazards

Storage Class

4.3 - Hazardous materials, which set free flammable gases upon contact with water

wgk_germany

WGK 3

flash_point_f

-2.2 °F - closed cup - Solvent

flash_point_c

-19 °C - closed cup - Solvent

ppe

Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter


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Zhaomin Hou et al.
Inorganic chemistry, 35(25), 7190-7195 (1996-12-04)
Synthesis of a new class of heteroleptic samarium aryloxide complexes has been achieved by the use of homoleptic samarium(II) bis(aryloxide) Sm(OAr)(2)(THF)(3) (1, Ar = C(6)H(2)Bu(t)(2)-2,6-Me-4) as a starting material, which is easily obtained by reaction of Sm(N(SiMe(3))(2))(2)(THF)(2) with 2 equiv
Aldrichimica Acta, 24, 15-15 (1991)
Application of lanthanide reagents in organic synthesis
Gary A. Molander
Chemical Reviews, 92, 29-29 (1992)
Asymmetric samarium-Reformatsky reaction of chiral α-bromoacetyl-2-oxazolidinones with aldehydes
Fukuzawa S-I, et al.
The Journal of Organic Chemistry, 65(6), 1702-1706 (2000)
Synthesis of Substituted Cyclooctanols by a Samarium(II) Iodide Promoted 8-Endo Radical Cyclization Process
Gary A. Molander and Jeffrey A. McKie
The Journal of Organic Chemistry, 59, 3186-3186 (1994)

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