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Safety Information

195529

Sigma-Aldrich

Iodotrimethylsilane

97%

Synonym(s):

TMIS, Trimethyliodosilane

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About This Item

Linear Formula:
(CH3)3SiI
CAS Number:
16029-98-4
Molecular Weight:
200.09
Beilstein:
1731136
EC Number:
240-171-0
MDL number:
MFCD00001028
UNSPSC Code:
12352103
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 Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

FSL

Group 4: Flammable liquids
Type 1 petroleums
Hazardous rank II
Water insoluble liquid

ISHL Indicated Name

Substances Subject to be Indicated Names

ISHL Notified Names

Substances Subject to be Notified Names

JAN Code

195529-BULK:
195529-5G:4548173986258
195529-VAR:
195529-100G:4548173986234
195529-25G:4548173986241

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Certificates of Analysis (COA)

Lot/Batch Number
MKCV4191
MKCQ8371
MKCN4247
MKCL5508
MKCH5066

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Tetrahedron Letters, 35, 5445-5445 (1994)
Erick J Rendón-Ramirez et al.
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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)
Go Hirai et al.
Bioorganic & medicinal chemistry letters, 14(10), 2647-2651 (2004-04-28)
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