Trimethylsulfonium iodide Chemical Properties

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

InChI

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

InChIKey

VFJYIHQDILEQNR-UHFFFAOYSA-M

SMILES

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

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

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36

WGK Germany 

3

RTECS 

WR8750000

F 

8

TSCA 

TSCA listed

HazardClass 

IRRITANT

HS Code 

29309070

Storage Class

11 - Combustible Solids

Hazard Classifications

Eye Irrit. 2
Skin Irrit. 2
STOT SE 3

MSDS

• Language:English Provider:Trimethylsulfonium iodide
• Language:English Provider:ACROS
• Language:English Provider:SigmaAldrich
• Language:English Provider:ALFA

Trimethylsulfonium iodide Usage And Synthesis

Chemical Properties

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

Uses

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.

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.

reaction suitability

reaction type: C-C Bond Formation

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.]

Trimethylsulfonium iodide(2181-42-2)Related Product Information

• Trimethylolpropane
• Potassium iodide
• Propidium iodide
• TRIMETHYLSILANE
• Trimethylsulfonium iodide, oxide
• Iodotrimethylsilane
• Trimethylsulfonium bromide
• Tris(hydroxymethyl)aminomethane
• PHENYLTRIMETHYLSILANE
• Trimethoxypropylsilane
• (Trifluoromethyl)trimethylsilane
• VINYLOXYTRIMETHYLSILANE
• Trimethylsilyl cyanide
• Trimethylsilylacetylene
• Trimethyloxonium Tetrafluoroborate
• Trimethyl phosphonoacetate
• Potassium trimethylsilanolate
• TRIMETHYLSULFOXONIUM CHLORIDE