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195529
Iodotrimethylsilane
Iodotrimethylsilane
97%
Synonyme(s) :
TMIS, Trimethyliodosilane
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5 G
49.60 CHF
25 G
114.00 CHF
100 G
263.00 CHF
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5 G
49.60 CHF
25 G
114.00 CHF
100 G
263.00 CHF
About This Item
Formule linéaire :
(CH3)3SiI
Numéro CAS:
Poids moléculaire :
200.09
Beilstein:
1731136
Numéro CE :
Numéro MDL:
Code UNSPSC :
12352103
ID de substance PubChem :
Nomenclature NACRES :
NA.22
Forme:
liquid
Essai:
97%
Produits recommandés
Niveau de qualité
Essai
97%
Forme
liquid
Contient
copper as stabilizer
Indice de réfraction
n20/D 1.471 (lit.)
pb
106 °C (lit.)
Densité
1.406 g/mL at 25 °C (lit.)
Température de stockage
−20°C
Chaîne SMILES
C[Si](C)(C)I
InChI
1S/C3H9ISi/c1-5(2,3)4/h1-3H3
Clé InChI
CSRZQMIRAZTJOY-UHFFFAOYSA-N
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Catégories apparentées
Description générale
Iodotrimethylsilane is a multipurpose reagent used in various organic reactions. It is used for the dealkylation of few compounds like lactones, ethers, acetals, and carbamates and trimethylsilylating agent for the synthesis of silyl imino esters, alkyl and alkenyl silanes, etc. It also acts as a Lewis acid catalyst and as a reducing agent in many organic reactions.[1][1]
[1]Iodotrimethylsilane is a hard-soft reagent that reacts readily with organic compounds containing oxygen (a hard base) forming a strong siliconoxygen bond.[2]
[1]Iodotrimethylsilane is a hard-soft reagent that reacts readily with organic compounds containing oxygen (a hard base) forming a strong siliconoxygen bond.[2]
Application
Efficient reagent for cleaving ethers, esters, carbamates, ketals, and lactones.[3]
For the introduction of the TMS group, e.g., TMS enol ethers.[4] Key reagent for the selective deprotection of an N-Cbz group in the presence of a trimethyltin moiety.[5]
Reagent was recently reported to convert allyl- and benzylphosphotriesters to the corresponding iodides.[6]
À utiliser avec
Réf. du produit
Description
Tarif
Mention d'avertissement
Danger
Mentions de danger
Conseils de prudence
Classification des risques
Eye Dam. 1 - Flam. Liq. 2 - Skin Corr. 1B
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 - closed cup
Point d'éclair (°C)
-31 °C - closed cup
Équipement de protection individuelle
Faceshields, Gloves, Goggles, type ABEK (EN14387) respirator filter
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Les clients ont également consulté
Tetrahedron Letters, 45, 3607-3607 (2004)
Iodotrimethylsilane?a versatile synthetic reagent
Olah GA, et al.
Tetrahedron, 38, 2225-2277 (1982)
Erick J Rendón-Ramirez et al.
Viral immunology, 28(5), 248-254 (2015-04-30)
There is a strong interest in finding adequate biomarkers to aid in the diagnosis and prognosis of influenza A (H1N1)pdm09 virus infection. In this study, serum levels of inflammatory cytokines and laboratory markers were evaluated to assess their usefulness as
Iodotrimethylsilane
e-EROS Encyclopedia of Reagents for Organic Synthesis (2005)
Tetrahedron Letters, 35, 5445-5445 (1994)
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What is known of the mechanism of reactions involving product 195529, Iodotrimethylsilane?
1 answer-
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.
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