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195529
Iodotrimethylsilane
Iodotrimethylsilane
97%
Synonym(s):
TMIS, Trimethyliodosilane
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5 G
$50.30
25 G
$130.00
100 G
$299.00
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5 G
$50.30
25 G
$130.00
100 G
$299.00
About This Item
Linear Formula:
(CH3)3SiI
CAS Number:
Molecular Weight:
200.09
Beilstein/REAXYS Number:
1731136
EC Number:
MDL number:
UNSPSC Code:
12352103
PubChem Substance ID:
NACRES:
NA.22
form:
liquid
assay:
97%
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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]
[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]
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Description
Pricing
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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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Iodotrimethylsilane?a versatile synthetic reagent
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Iodotrimethylsilane
e-EROS Encyclopedia of Reagents for Organic Synthesis (2005)
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What is known of the mechanism of reactions involving product 195529, Iodotrimethylsilane?
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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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