The mechanism for cleavage of esters is described in PNAS, 75(1), 4-6 (1978).The authors go on to explain that the data do not support a previously published mechanism via a carbenium iodide.The paper also discusses the cleavage of ethers using iodotrimethylsilane. It appears that this is not as efficient as cleavage of esters, and a couple of mechanisms (pages 5 and 6) are proposed.Olah also described the cleavage of the phosphate esters in peptides that contain phosphate esters, using iodotrimethylsilane (Tetrahedron, 38, 2225 (1982)). The amide linkages in the peptide backbone are not cleaved.
748854
Iodotrimethylsilane solution
1 M in dichloromethane
Synonyme(s) :
Iodotrimethylsilane solution, TMS iodine, TMS-I, TMSI, Trimethyliodosilane
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100 ML
391.00 CHF
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100 ML
391.00 CHF
About This Item
Formule empirique (notation de Hill) :
C3H9ISi
Poids moléculaire :
200.09
Code UNSPSC :
12352101
Nomenclature NACRES :
NA.22
Produits recommandés
Forme
liquid
Niveau de qualité
Concentration
1 M in dichloromethane
Indice de réfraction
n20/D 1.433
Densité
1.334 g/mL at 25 °C
Température de stockage
2-8°C
Catégories apparentées
Description générale
Iodotrimethylsilane [(CH3)3SiI] is an important and versatile organosilicon reagent with wide applications in organic synthesis. It is used as a neutral nucleophilic reagent, trimethylsilylating agent, Lewis acid catalyst, reducing agent and dehydrating agent in many organic reactions.[1]
Mention d'avertissement
Danger
Mentions de danger
Classification des risques
Carc. 2 - Eye Dam. 1 - Flam. Liq. 2 - Skin Corr. 1B - STOT SE 3
Organes cibles
Central nervous system
Risques supp
Code de la classe de stockage
3 - Flammable liquids
Classe de danger pour l'eau (WGK)
WGK 3
Point d'éclair (°F)
-23.8 °F
Point d'éclair (°C)
-31 °C
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Regio-and stereospecific synthesis of (E)-α-iodoenamide moieties from ynamides through iodotrimethylsilane-mediated hydroiodation
Sato AH, et al.
Tetrahedron Letters, 54(10), 1309-1311 (2013)
One-step synthesis of (1-iodovinyl) arenes from trimethylsilyl ethynylarene through iodotrimethylsilane-mediated hydroiodation
Sato AH, et al.
Tetrahedron Letters, 53(28), 3585-3589 (2012)
Iodotrimethylsilane
Encyclopedia of Reagents for Organic Synthesis, Second Edition (2005)
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