195529
Iodotrimethylsilane
97%
Synonym(s):
TMIS, Trimethyliodosilane
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About This Item
Linear Formula:
(CH3)3SiI
CAS Number:
Molecular Weight:
200.09
UNSPSC Code:
12352103
NACRES:
NA.22
PubChem Substance ID:
EC Number:
240-171-0
Beilstein/REAXYS Number:
1731136
MDL number:
Assay:
97%
Form:
liquid
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
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.
Iodotrimethylsilane is a hard-soft reagent that reacts readily with organic compounds containing oxygen (a hard base) forming a strong siliconoxygen bond.
Application
Reagent was recently reported to convert allyl- and benzylphosphotriesters to the corresponding iodides.
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.
Disclaimer
Supply conditions do not apply to the regions and states of Brazil: North, Northeast, Mato Grosso do Sul, Mato Grosso, and Rio Grande do Sul.
signalword
Danger
hcodes
Hazard Classifications
Eye Dam. 1 - Flam. Liq. 2 - Skin Corr. 1B
supp_hazards
Storage Class
3 - Flammable liquids
wgk
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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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)
Tetrahedron Letters, 35, 5445-5445 (1994)