Samarium(3+);triiodide

Base Information

• Chemical Name: Samarium(3+);triiodide
• CAS No.: 13813-25-7
• Molecular Formula: I3Sm
• Molecular Weight: 531.073
• Nikkaji Number: J134.358K
• Mol file: 13813-25-7.mol

Synonyms:samarium(3+);triiodide;Samarium(iii)iodide;XQKBFQXWZCFNFF-UHFFFAOYSA-K

Chemical Property of Samarium(3+);triiodide

Chemical Property:

• Melting Point: 850°C
• Boiling Point: 127°Cat760mmHg
• Flash Point: °C
• PSA: 0.00000
• Density: g/cm³
• LogP: 2.65710
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 0
• Exact Mass: 532.6332
• Heavy Atom Count: 4
• Complexity: 0

Purity/Quality:

98%,99%, ^*data from raw suppliers

Samarium(III) iodide anhydrous, powder ^*data from reagent suppliers

Safty Information:

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: [I-].[I-].[I-].[Sm+3]
• General Description: Samarium(III) iodide (SmI3), also known as samarium triiodide or samarium iodide, is demonstrated to be an effective promoter for Michael addition reactions of active methylene compounds to chalcones under mild, neutral conditions. It facilitates the formation of 1,4-adducts in moderate to good yields, with higher efficiency observed for substrates like malononitrile, β-ketoester, diethylmalonate, and nitromethane compared to ethylcyanoacetate. This highlights its utility as a versatile reagent in organic synthesis for selective transformations.

Technology Process of Samarium(3+);triiodide

There total 13 articles about Samarium(3+);triiodide which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 99.0%

[Sm(water)9](I)3 → samarium(III) iodide (13813-25-7)

Guidance literature:

In neat (no solvent, solid phase); byproducts: H2O; Schlenk techniques; heating Sm compd. under vacuum (1E-3 Torr);

DOI:10.1016/j.poly.2010.02.027

Reference yield: 95.0%

samarium diiodide (32248-43-4) + 1,3,5,7-cycloocatetraene → samarium(III) iodide (13813-25-7) + iodo(η8-cyclooctatetraene)(tetrahydrofuran)samarium (126075-48-7)

Guidance literature:

With tetrahydrofurane; In tetrahydrofuran; Ar; few min;; soln. concd.; crystd.;;

DOI:10.1016/0022-328X(94)80108-8

Reference yield: 77.0%

samarium (7440-19-9) + mercury(II) iodide → samarium(III) iodide (13813-25-7) + samarium diiodide(tetrahydrofuran)2 + mercury

Guidance literature:

With tetrahydrofuran; In tetrahydrofuran; React. of HgI2 with excess Sm under N2 in refluxing THF gives yellow (SmI3) and grey (Hg) suspn. in 0.5 h, a blue-green colour (SmI2) develops, heating (8 h).; Filtn., evapn.;

DOI:10.1246/cl.1999.837

upstream raw materials:

aluminium(III) iodide

hydrogen iodide

samarium

iodine

Downstream raw materials:

samarium diiodide

[Sm(C₁₇H₁₆N₄O₃)2I₂]⁽¹⁺⁾*I^(1-) = [Sm(C₁₇H₁₆N₄O₃)2I₂]I

Sm(C₆H₅N₂C₃(CH₃)2(CHO)O)4I₂⁽¹⁺⁾*I^(1-)=[Sm(C₆H₅N₂C₃(CH₃)2(CHO)O)4I₂]I

[(2,5-bis(N-(2,6-diisopropylphenyl)iminomethyl)pyrrolyl)SmI₂(thf)]2

Refernces

Toluates: unexpectedly versatile reagents

10.1016/j.tet.2009.09.111

The study investigates the monoelectronic reduction mechanism of aromatic esters, with a particular focus on the synthetic utility of the toluate moiety in deoxygenation of alcohols and allylation of ketones. It also explores the use of aromatic esters as protective groups that can be easily removed. Chemicals used in the study include aromatic esters like toluates and benzoates, which serve as reagents and protective groups, and reducing agents such as samarium iodide (SmI2) and hexamethylphosphoramide (HMPA). These chemicals were employed to elucidate the reduction mechanism, develop novel synthetic reactions, and achieve selective deoxygenation and allylation reactions. The study also involved electrochemical techniques to perform metal-free reactions and deprotection of aromatic esters, demonstrating the versatility of toluates in organic synthesis and the potential of electrosynthesis for selective chemical transformations.

Michael additions of active methylene compounds to chalcones promoted by samarium(III) iodide

10.1081/SCC-120002689

The research investigates the Michael addition reactions of active methylene compounds to chalcones, which are α,β-unsaturated ketones, promoted by samarium(III) iodide (SmI3). The reactions are carried out under neutral, mild conditions, avoiding some side reactions that occur in traditional base-promoted reactions. The results show that the reactions generally yield 1,4-adducts in moderate to good yields, with malononitrile, β-ketoester, diethylmalonate, and nitromethane typically producing higher yields compared to ethylcyanoacetate. The study highlights the potential of SmI3 as a promoter for Michael addition reactions in organic synthesis.

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