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- Brand Name:ZSpharmac
Product Name:
SAMARIUM(II) IODIDE
Synonyms:
SaMariuM(II) iodide, 0.1M in THF, SMI2;(ca. 0.1Mol/L in Tetrahydrofuran);SaMariuM(II) Iodide ;SaMariuM(II) iodide anhydrous, powder, >=99.9% trace Metals basis;SaMariuM(II) iodide solution 0.1 M in THF, contains saMariuM chips as stabilizer;Samarium(II) iodide, 0.1M solution in THF,
0.1M solution in THF, Stabilized with samarium powder;SaMariuM Iodide, Anhydrous, -20 Mesh;Samarium(II)
iodide solution, 0.07-0.12M in THF, stabilized
CAS:
32248-43-4
MF:
I2Sm
MW:
404.17
EINECS:
203-726-8
Product Categories:
catalyst raw material; chemical raw material
Mol File:
Melting point ：
526 ±3°
Boiling point ：
solid: 1580℃ [CRC10]
density ：
0.922 g/mL at 25 °C
Fp ：
−2 °F
storage temp. ：
2-8°C
form ：
powder
color ：
Deep blue-green
Sensitive ：
Air & Moisture Sensitive
Merck ：
14,8349
Reaction：
SmI2 has been used extensively in literature due to its large reduction potential. Known as a single-electron transfer reagent.
Mechanism of SmI2-mediated Reactions：
Radicals and anions from organohalides
Reduction of halides: iodides > bromides > chloride
reaction carried out at 60 °C
Chemical Properties
Deep bleu-green solution
Uses：
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.
Uses：
In organic synthesis and electron transfer reactions; in discharge lamps.
Purification Methods：
A possible impurity is SmI3 from which it is made. If present, grind the solid to a powder and heat it in a stream of pure H2. The temperature (~ 500-600o) should be below the m (~ 628o) of
SmI3, since the molten compounds react very slowly. [Wetzel in Handbook of Preparative Inorganic Chemistry (Ed. Brauer) Academic Press Vol II pp 1149, 1150 1965.]
