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195529

Sigma-Aldrich

Iodotrimethylsilane

97%

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Synonym(s):
TMIS, Trimethyliodosilane
Linear Formula:
(CH3)3SiI
CAS Number:
16029-98-4
Molecular Weight:
200.09
Beilstein:
1731136
EC Number:
240-171-0
MDL number:
MFCD00001028
PubChem Substance ID:
24851696
NACRES:
NA.22

Quality Level

300

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.

Iodotrimethylsilane is a hard-soft reagent that reacts readily with organic compounds containing oxygen (a hard base) forming a strong siliconoxygen bond.

Application

Efficient reagent for cleaving ethers, esters, carbamates, ketals, and lactones.
For the introduction of the TMS group, e.g., TMS enol ethers. Key reagent for the selective deprotection of an N-Cbz group in the presence of a trimethyltin moiety.
Reagent was recently reported to convert allyl- and benzylphosphotriesters to the corresponding iodides.

accessory

Product No.
Description
Pricing

Pictograms

FlameCorrosion
GHS02,GHS05

Signal Word

Danger

Hazard Statements

H225 - H314

Hazard Classifications

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

Supplementary Hazards

EUH014

Storage Class Code

3 - Flammable liquids

WGK

WGK 3

Flash Point(F)

-23.8 °F - closed cup

Flash Point(C)

-31 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Information

危险化学品

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

    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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Iodotrimethylsilane
e-EROS Encyclopedia of Reagents for Organic Synthesis. (2005)
Iodotrimethylsilane?a versatile synthetic reagent
Olah GA, et al.
Tetrahedron, 38, 2225-2277 (1982)
Tetrahedron Letters, 35, 5445-5445 (1994)
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)
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