Consentement d'utilisation des Cookies

J'accepte Notre site sauvegarde des traceurs textes (cookies) sur votre appareil afin de vous garantir de meilleurs contenus et à des fins de collectes statistiques.Vous pouvez désactiver l'usage des cookies en changeant les paramètres de votre navigateur. En poursuivant votre navigation sur notre site sans changer vos paramètres de navigateur vous nous accordez la permission de conserver des informations sur votre appareil.

2181-42-2 - Trimethylsulfonium iodide, 99% - A12639 - Alfa Aesar

A12639 Trimethylsulfonium iodide, 99%

Numéro CAS
2181-42-2
Synonymes

Dimensions Prix ($) Quantité Disponibilité
50g 45,70
250g 191,00
1000g 700,00
Ajouter au panier Ajouter au devis en vrac Afficher l'article

Trimethylsulfonium iodide, 99%

MDL
MFCD00011632
EINECS
218-555-4

Propriétés chimiques

Formule
(CH3)3SI
Poids formulaire
204.07
Point de fusion
ca 215° subl.
Sensibilité
Light Sensitive

Références bibliographiques

The ylide, generated with strong base, is a powerful methylene transfer reagent, converting aldehydes and ketones to epoxides; reaction with ɑß-enones also gives epoxides (contrast Trimethyl­sulfoxonium iodide, A14589): J. Am. Chem. Soc., 87, 1353 (1965):

/n

Other conditions for addition to aldehydes include: phase-transfer catalysis: Angew. Chem. Int. Ed., 12, 845 (1973), KOH in acetonitrile: Tetrahedron Lett., 23, 5283 (1982), or KF on alumina: Tetrahedron, 41, 1259 (1985). With aryl aldehydes, the use of KO-t-Bu gives improved results by suppressing the competing Cannizzaro reaction: Org. Prep. Proced. Int., 27, 219 (1995). A simplified, solvent-free method employing KO-t-Bu has been reported for ketones: Heterocycles, 46, 185 (1997). With excess of the sulfonium ylide, ketones or epoxides give good yields of allylic alcohols, whereas aldehydes give poor yields. Under similar conditions, the sulfoxonium ylide gives oxetanes: Tetrahedron Lett., 35, 2009, 5449 (1994).

/n

Methylene transfer to imines and arylhydrazones gives aziridines and N-arylaminoaziridines respectively: Synthesis, 330 (1983).

/n

Addition to vinyl sulfones gives cyclopropyl sulfones: J. Org. Chem., 29, 3277 (1964). Similarly, vinylsulfonates and sulfonamides give cyclopropanes in fair to good yields: J. Org. Chem., 33, 3849 (1968).

/n

Methylene transfer to allylic, propargylic, benzylic and primary alkyl halides and sulfonates results in formation of terminal alkenes in generally good yields: Tetrahedron Lett., 35, 5453 (1994).

/n

Reaction with Ag2O gives the corresponding hydroxide, which is a useful methylating agent for various functional groups, including carboxylic acids, phenols, thiols and N-heterocycles: J. Org. Chem., 44, 638 (1979). Both the iodide and the hydroxide have been used for the methylation of pyrimidine nucleosides; see, e.g.: J. Chem. Soc., Perkin 1, 13 (1989).

/n

Mentions de danger et de prudence du SGH

Mentions de danger (UE): H315-H319-H335

Causes skin irritation. Causes serious eye irritation. May cause respiratory irritation.

Mentions de prudence: P261-P280-P305+P351+P338-P304+P340-P362-P312-P321-P405-P403+P233-P501a

Avoid breathing dust/fume/gas/mist/vapours/spray. Wear protective gloves/protective clothing/eye protection/face protection. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. IF INHALED: Remove to fresh air and keep at rest in a position comfortable for breathing. Take off contaminated clothing and wash before reuse. Call a POISON CENTER or doctor/physician if you feel unwell. Specific treatment (see label). Store locked up. Store in a well-ventilated place. Keep container tightly closed. Dispose of contents/container in accordance with local/regional/national/international regulations.

Autres références

Beilstein
3555192
Code tarifaire harmonisé
2930.90
TSCA
Yes
RTECS
WR8750000

Recommandé

  • A10478

    2,6-Lutidine, 98+%
  • A12824

    2-Methyl-1,3-dioxolane, 98%
  • A13320

    3-Quinuclidinone hydrochloride, 98+%
  • A13947

    Potassium tert-butoxide, 97%
  • 42780

    Dimethyl sulfoxide, HPLC grade, 99.9+%, packaged under Argon in resealable ChemSeal™ bottles

Consulté récemment

Produits chimiques

Sciences de la vie

Métaux et matériaux

Catalyseurs

Analytique et matériel de laboratoire