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HomeProduct name listTrimethylsulfonium iodide

Trimethylsulfonium iodide

  • CAS NO.:2181-42-2
  • Empirical Formula: C3H9IS
  • Molecular Weight: 204.07
  • MDL number: MFCD00011632
  • EINECS: 218-555-4
  • SAFETY DATA SHEET (SDS)
  • Update Date: 2024-08-22 14:21:17
Trimethylsulfonium iodide Structural

What is Trimethylsulfonium iodide?

Chemical properties

white to yellowish crystalline solid. Soluble in water, alcohol, tetrahydrofuran, dimethyl sulfoxide.

The Uses of Trimethylsulfonium iodide

Trimethylsulfonium iodide is a salt that is usually dissolved in strong base in order to synthesize epoxides in-situ. Trimethylsulfonium iodide also has the potential to inhibit human placental diamine oxidase.

What are the applications of Application

Trimethylsulfonium Iodide is a sulfoxonium salt. It is used to Treatment with strong base yields the dimethylsulfonium methylide which reacts in-situ with the carbonyl group of ketones to form epoxides or allylic alcohols.

Preparation

Trimethylsulfoxonium iodide may be prepared by the reaction of dimethyl sulfoxide and iodomethane:
(CH3)2SO + CH3I → (CH3)3SO+I
After standing overnight, the resulting solid white cake is crushed and recrystallized from absolute ethanol to give pure trimethylsulfonium iodide.

Purification Methods

Crystallise the iodide from EtOH. [Emeleus & Heal J Chem Soc 1126 1946, Swain & Kaiser J Am Chem Soc 80 4089 1958, Borredon et al. J Org Chem 55 501 1990, Bouda et al. Synth Commun 17 503 1987.]

Properties of Trimethylsulfonium iodide

Melting point: 215-220 °C (lit.)
Density  1.6554 (estimate)
storage temp.  Keep in dark place,Inert atmosphere,Room temperature
solubility  Soluble in water, alcohol, THF, DMSO
form  Crystalline Powder, Crystals and/or Chunks
color  White to yellow
Water Solubility  soluble
Sensitive  Light Sensitive
BRN  3555192
Exposure limits ACGIH: TWA 0.01 ppm
CAS DataBase Reference 2181-42-2(CAS DataBase Reference)
NIST Chemistry Reference Trimethylsulfonium iodide(2181-42-2)
EPA Substance Registry System Trimethylsulfonium iodide (2181-42-2)

Safety information for Trimethylsulfonium iodide

Signal word Warning
Pictogram(s)
ghs
Exclamation Mark
Irritant
GHS07
GHS Hazard Statements H315:Skin corrosion/irritation
H319:Serious eye damage/eye irritation
H335:Specific target organ toxicity, single exposure;Respiratory tract irritation
Precautionary Statement Codes P261:Avoid breathing dust/fume/gas/mist/vapours/spray.
P264:Wash hands thoroughly after handling.
P264:Wash skin thouroughly after handling.
P271:Use only outdoors or in a well-ventilated area.
P280:Wear protective gloves/protective clothing/eye protection/face protection.
P302+P352:IF ON SKIN: wash with plenty of soap and water.
P305+P351+P338:IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

Computed Descriptors for Trimethylsulfonium iodide

InChIKey VFJYIHQDILEQNR-UHFFFAOYSA-M

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