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Key Documents

57903

Sigma-Aldrich

(Iodomethyl)trimethylsilane

≥99.0% (GC)

Synonym(s):

(Trimethylsilyl)methyl iodide

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About This Item

Linear Formula:
(CH3)3SiCH2I
CAS Number:
Molecular Weight:
214.12
Beilstein:
1731485
EC Number:
MDL number:
UNSPSC Code:
12352103
PubChem Substance ID:
NACRES:
NA.22

Quality Level

Assay

≥99.0% (GC)

refractive index

n20/D 1.491 (lit.)
n20/D 1.491

bp

139-141 °C (lit.)

density

1.443 g/mL at 25 °C (lit.)

functional group

iodo

SMILES string

C[Si](C)(C)CI

InChI

1S/C4H11ISi/c1-6(2,3)4-5/h4H2,1-3H3

InChI key

VZNYXGQMDSRJAL-UHFFFAOYSA-N

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Other Notes

Starting material for the preparation of 2-(trimethylsilyl)ethyl-triphenylphosphonium iodide used for the synthesis of allyl silanes; Used for the N-alkylation of amides, in a reaction sequence to prepare unstabilized ylides for [2+3]-cycloadditions

Pictograms

FlameExclamation mark

Signal Word

Warning

Hazard Statements

Hazard Classifications

Eye Irrit. 2 - Flam. Liq. 3 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

3 - Flammable liquids

WGK

WGK 3

Flash Point(F)

84.2 °F - closed cup

Flash Point(C)

29 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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I. Fleming et al.
Synthesis, 446-446 (1979)
D. Seyferth et al.
The Journal of Organic Chemistry, 42, 3104-3104 (1977)
E. Vedejs et al.
The Journal of Organic Chemistry, 50, 2170-2170 (1985)
E. Vedejs et al.
The Journal of Organic Chemistry, 48, 4773-4773 (1983)

Articles

This review outlines the sustainable reactions occurring through the SET mechanism, leading to the formation of carbon-carbon bonds and rearrangement of oxaziridines in photoredox catalysis using newly developed neutral silicon-based radical precursors.

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