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: 2024-11-18 17:43:10
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) |
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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