Trimethylsulfonium iodide

Trimethylsulfonium iodide
  • CAS No.:2181-42-2
Other grades of this product :
Trimethylsulfonium iodide Basic information
Product Name:Trimethylsulfonium iodide
Synonyms:Trimethylsulfonium iodine;trimethylsulfone iodide;Trimethylsulfoniumiodid;Trimethylsulfonium iodide,98%;Trimethylsulfonium iodide ,99.5%;Trimethylsulphonium Iodide 99%;triMethylsulfaniuM iodide;TriMethylsulfoniuM iodide, 98% 100GR
CAS:2181-42-2
MF:C3H9IS
MW:204.07
EINECS:218-555-4
Product Categories:C-C Bond Formation;OthersOrganic Building Blocks;Iodonium Sulfonium & Oxonium Compounds;Sulfonium/Sulfoxonium Compounds;Sulfur Compounds;Synthetic Reagents;Sulfonium Compounds;Isoquinolines ,Furans ,Quinolines ,Quinaldines
Mol File:2181-42-2.mol
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 limitsACGIH: TWA 0.01 ppm
InChIKeyVFJYIHQDILEQNR-UHFFFAOYSA-M
CAS DataBase Reference2181-42-2(CAS DataBase Reference)
NIST Chemistry ReferenceTrimethylsulfonium iodide(2181-42-2)
EPA Substance Registry SystemTrimethylsulfonium iodide (2181-42-2)
Safety Information
Hazard Codes Xi
Risk Statements 36/37/38
Safety Statements 26-36
WGK Germany 3
RTECS WR8750000
8
TSCA Yes
HazardClass IRRITANT
HS Code 29309070
MSDS Information
ProviderLanguage
Trimethylsulfonium iodide English
ACROS English
SigmaAldrich English
ALFA English
Trimethylsulfonium iodide Usage And Synthesis
Chemical Propertieswhite to yellowish crystalline solid. Soluble in water, alcohol, tetrahydrofuran, dimethyl sulfoxide.
UsesTrimethylsulfonium 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.
ApplicationTrimethylsulfonium 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.
PreparationTrimethylsulfoxonium iodide may be prepared by the reaction of dimethyl sulfoxide and iodomethane:(CH3)2SO + CH3I → (CH3)3SO+IAfter standing overnight, the resulting solid white cake is crushed and recrystallized from absolute ethanol to give pure trimethylsulfonium iodide.
Purification MethodsCrystallise 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 Preparation Products And Raw materials
Raw materialsMETHALLYLSULPHIDE-->ETHOXYSILATRANE-->1,3,5-TRITHIANE
Preparation Products3-Phenylpropene-3-ol-->3,4-epoxy-2-methyl-1-butene-->METHYLDIPHENYLPHOSPHINE

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