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| 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: | Other Metal;metal halide;OthersChemical Synthesis;Catalysis and Inorganic Chemistry;Reduction;Salts;Classes of Metal Compounds;Sm (Samarium) Compounds;Transition Metal Compounds;Samarium Salts;SamariumMetal and Ceramic Science;Synthetic Reagents;Crystal Grade Inorganics | | Mol File: | 32248-43-4.mol |  |
| | SAMARIUM(II) IODIDE Chemical Properties |
| 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 | | Exposure limits | ACGIH: TWA 50 ppm; STEL 100 ppm (Skin)
OSHA: TWA 200 ppm(590 mg/m3)
NIOSH: IDLH 2000 ppm; TWA 200 ppm(590 mg/m3); STEL 250 ppm(735 mg/m3) | | InChIKey | UAWABSHMGXMCRK-UHFFFAOYSA-L | | CAS DataBase Reference | 32248-43-4(CAS DataBase Reference) |
| | SAMARIUM(II) IODIDE Usage And Synthesis |
| 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 | In organic synthesis and electron transfer reactions; in discharge lamps. | | 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. | | 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.] |
| | SAMARIUM(II) IODIDE Preparation Products And Raw materials |
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