Trimethylsulfoniumiodid

Strukturformel
Strukturformel von Trimethylsulfonium-Ion
Allgemeines
Name Trimethylsulfoniumiodid
Summenformel C3H9IS
Kurzbeschreibung

farbloser Feststoff[1]

Externe Identifikatoren/Datenbanken
CAS-Nummer 2181-42-2
EG-Nummer 218-555-4
ECHA-InfoCard 100.016.869
PubChem 75127
Wikidata Q2453392
Eigenschaften
Molare Masse 204,06 g·mol−1
Aggregatzustand

fest

Dichte

0,63 g·cm−3 (Schüttdichte)[2]

Schmelzpunkt

215–220 °C[1]

Löslichkeit

gut löslich in Wasser (400 g/l bei 20 °C)[2]

Sicherheitshinweise
GHS-Gefahrstoffkennzeichnung[2]
Gefahrensymbol

Achtung

H- und P-Sätze H: 315​‐​319​‐​335
P: 302+352​‐​304+340​‐​305+351+338[2]
Soweit möglich und gebräuchlich, werden SI-Einheiten verwendet.
Wenn nicht anders vermerkt, gelten die angegebenen Daten bei Standardbedingungen (0 °C, 1000 hPa).

Trimethylsulfoniumiodid, mit der Konstitutionsformel S(CH3)3I, ist eine chemische Verbindung aus der Gruppe der Sulfoniumverbindungen.

Gewinnung und Darstellung

Trimethylsulfoniumiodid kann durch Substitutionsreaktion von Dimethylsulfid mit Iodmethan gewonnen werden.[3]

Eigenschaften

Trimethylsulfoniumiodid ist ein farbloser Feststoff, der gut löslich in Wasser ist.[2] Es kristallisiert in einem monoklinen Kristallsystem mit zwei (CH3)3SI-Einheiten in der Elementarzelle.[4]

Verwendung

Trimethylsulfoniumiodid wird als Zwischenprodukt bei der Herstellung verschiedener Pflanzenschutzmittel verwendet. Es ist ein starkes Methylen-Transfer-Reagenz, mit dem Aldehyde und Ketone zu Epoxiden umgesetzt werden können.[5]

Einzelnachweise

  1. ↑ a b Datenblatt Trimethylsulfonium iodide, 98 % bei Sigma-Aldrich, abgerufen am 2. Januar 2012 (PDF).
  2. ↑ a b c d e Datenblatt Trimethylsulfoniumiodid bei Merck, abgerufen am 2. Januar 2012.
  3. ↑ Thomas N. Sorrell: Organic chemistry. 2006, ISBN 978-1-891389-38-2 (Seite 228 in der Google-Buchsuche).
  4. ↑ M. Jannin, R. Puget et al.: Structures of trimethylsulfonium salts. I. Refinement of the structure of the iodide (CH3)3SI. In: Acta Crystallographica Section C Crystal Structure Communications. 47, S. 982, doi:10.1107/S0108270190008095.
  5. ↑ Datenblatt Trimethylsulfonium iodide bei Alfa Aesar, abgerufen am 15. Juli 2016 (Seite nicht mehr abrufbar).

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