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Merck

T80489

Trimethylsulfonium iodide

98%

Synonym(s):

Trimethyl-λ[3]-sulfane hydroiodide, Trimethylsulphonium iodide

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About This Item

Linear Formula:
(CH3)3S(I)
CAS Number:
2181-42-2
Molecular Weight:
204.07
UNSPSC Code:
12352101
NACRES:
NA.22
PubChem Substance ID:
24900497
EC Number:
218-555-4
Beilstein/REAXYS Number:
3555192
MDL number:
MFCD00011632

Key Documents

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Product Name

Trimethylsulfonium iodide, 98%

InChI key

VFJYIHQDILEQNR-UHFFFAOYSA-M

InChI

1S/C3H9S.HI/c1-4(2)3;/h1-3H3;1H/q+1;/p-1

SMILES string

[I-].C[S+](C)C

assay

98%

reaction suitability

reaction type: C-C Bond Formation

mp

215-220 °C (lit.)

Quality Level

200

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Application

Treatment with strong base yields the dimethylsulfonium methylide which reacts in-situ with the carbonyl group of ketones to form epoxides or allylic alcohols.

General description

Trimethylsulfonium iodide is commonly used as a methylating agent in organic synthesis.

pictograms

Exclamation mark
GHS07

signalword

Warning

Hazard Classifications

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

target_organs

Respiratory system

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
1425114
11709KO
11714CH
11614CH
01513BH

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H Castejon et al.
Journal of the American Chemical Society, 123(25), 6092-6097 (2001-06-21)
The reaction of ammonia and pyridine with trimethylsulfonium ion has been studied in gas phase and solution. Density functional theory at the B3LYP/6-31+G level was used to describe the energy changes along the reaction coordinate in the gas phase, and
Facile access to S-methyl dithiocarbamates with sulfonium or sulfoxonium iodide as a methylation reagent
Deng H, et al.
Organic & Biomolecular Chemistry, 21(32), 6474-6478 (2023)
Tetrahedron Letters, 35, 2009-2009 (1994)
K D Müller et al.
Zentralblatt fur Bakteriologie : international journal of medical microbiology, 274(2), 174-182 (1990-11-01)
Gas-liquid chromatography of cellular fatty acids is a useful tool for the identification of bacteria. Derivatization of bacterial fatty acids to methyl esters by conventional techniques is usually time-consuming and complicated. A new one-step technique using trimethyl-sulfonium hydroxide allows the
K Müller et al.
Journal of clinical microbiology, 36(9), 2477-2480 (1998-08-15)
The MIDI automated Microbial Identification System (MIS) uses gas chromatography (GC) analysis of whole-cell fatty acid methyl esters (FAMEs) between 9 and 20 carbons in length to characterize a wide range of bacterial genera and species, including mycobacteria. Mycolic acid
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