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Merck

195529

Sigma-Aldrich

Iodotrimethylsilane

Iodotrimethylsilane

97%

Sinónimos:

TMIS, Trimethyliodosilane

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5 G
MXP 1,050.00
25 G
MXP 2,708.00
100 G
MXP 6,246.00

MXP 1,050.00


Fecha estimada de envío02 de abril de 2025


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5 G
MXP 1,050.00
25 G
MXP 2,708.00
100 G
MXP 6,246.00

About This Item

Fórmula lineal:
(CH3)3SiI
Número de CAS:
Peso molecular:
200.09
Beilstein/REAXYS Number:
1731136
EC Number:
MDL number:
UNSPSC Code:
12352103
PubChem Substance ID:
NACRES:
NA.22

MXP 1,050.00


Fecha estimada de envío02 de abril de 2025


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Quality Level

assay

97%

form

liquid

contains

copper as stabilizer

refractive index

n20/D 1.471 (lit.)

bp

106 °C (lit.)

density

1.406 g/mL at 25 °C (lit.)

storage temp.

−20°C

SMILES string

C[Si](C)(C)I

InChI

1S/C3H9ISi/c1-5(2,3)4/h1-3H3

Inchi Key

CSRZQMIRAZTJOY-UHFFFAOYSA-N

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General description

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]

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]

For use with

Referencia del producto
Descripción
Precios

pictograms

FlameCorrosion

signalword

Danger

hcodes

Hazard Classifications

Eye Dam. 1 - Flam. Liq. 2 - Skin Corr. 1B

supp_hazards

Storage Class

3 - Flammable liquids

wgk_germany

WGK 3

flash_point_f

-23.8 °F - closed cup

flash_point_c

-31 °C - closed cup

ppe

Faceshields, Gloves, Goggles, type ABEK (EN14387) respirator filter


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Tetrahedron Letters, 35, 5445-5445 (1994)
Iodotrimethylsilane?a versatile synthetic reagent
Olah GA, et al.
Tetrahedron, 38, 2225-2277 (1982)
Go Hirai et al.
Bioorganic & medicinal chemistry letters, 14(10), 2647-2651 (2004-04-28)
Zoanthamines are a family of marine alkaloids that have complex heptacyclic structures and are reported to be interleukin-6 modulators. While the structure of zoanthamines, especially the ABC-ring portion, is similar to that of steroids, the CDEFG-ring portion, composed of aminoacetal
Iodotrimethylsilane
e-EROS Encyclopedia of Reagents for Organic Synthesis (2005)
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

Questions

1–2 of 2 Questions  
  1. What is the Department of Transportation shipping information for this product?

    1 answer
    1. Transportation information can be found in Section 14 of the product's (M)SDS.To access the shipping information for this material, use the link on the product detail page for the product.

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  2. What is known of the mechanism of reactions involving product 195529, Iodotrimethylsilane?

    1 answer
    1. 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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Reviews

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  1. Ontario
    • Review 1
    • Votes 0
    1 out of 5 stars.

    wrong structure

    The structure of the mentioned title and CAS No. do not match.

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