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.

1774-47-6 - Trimethylsulfoxonium iodide, 98+% - A14589 - Alfa Aesar

A14589 Trimethylsulfoxonium iodide, 98+%

Numéro CAS
1774-47-6
Synonymes

Dimensions Prix ($) Quantité Disponibilité
25g 15,84
100g 39,45
500g 133,90
Ajouter au panier Ajouter au devis en vrac Afficher l'article

Trimethylsulfoxonium iodide, 98+%

MDL
MFCD00011899
EINECS
217-204-2

Propriétés chimiques

Formule
(CH3)3SOI
Poids formulaire
220.07
Point de fusion
ca 170° dec.
Sensibilité
Light Sensitive
Solubilité
Soluble in water.

Applications

Trimethylsulfoxonium iodide reacts with sodium hydride to prepare dimethyloxosulfonium methylide, which is used as a methylene-transfer reagent in synthetic chemistry. It is used to prepare ylide, which reacts with carbonyl compounds to get epoxides. Further, it reacts with alfa,beta-unsaturated esters to get cyclopropyl esters.

Notes

Incompatible with strong oxidizing agents and strong bases. Light sensitive.

Références bibliographiques

The ylide, generated with strong base, is a methylene transfer reagent.

For an example (conversion of cyclohexanone to the epoxide), see: Org. Synth. Coll., 5, 755 (1973). In contrast to Trimethyl­sulfonium iodide, A12639, reaction with ɑß-unsaturated ketones occurs by 1,4-addition to give cyclopropanes: J. Am. Chem. Soc., 87, 1353 (1965):

Efficient addition to enones has been effected with a highly basic system consisting of KOH in DMSO with a phase-transfer catalyst: Synth. Commun., 26, 1785 (1996).

Reaction with epoxides gives oxetanes, unlike the sulfonium ylide which gives allylic alcohols: J. Org. Chem., 48, 5133 (1983); Synthesis, 1140 (1987); cf Tetrahedron Lett., 35, 5449 (1994):

Similarly, N-arenesulfonylaziridines undergo ring expansion to azetidines with inversion at one carbon. Thus, cis-substituted aziridines give trans-azetidines and vice versa: Tetrahedron, 45, 1851 (1989):

Review of the chemistry of sulfonium ylides: Russ. Chem. Rev., 50, 481 (1981). Extensive review of the synthetic applications of dimethylsulfoxonium methylide: Tetrahedron, 43, 2609 (1987).

Sathishkumar, S.; Mahasampathgowri, S.; Balasubramanian, K. K.; Saiganesh, R. A convenient synthesis of dialkyl 2-(2-haloethylidene)malonates, cyanoacetates and halocrotonates by one carbon extension. Tetrahedron Lett. 2015, 56 (26), 4031-4035.

Kagawa, N.; Suzuki, M.; Kogure, N.; Toume, K. Characterization of organic iodides with iodine-127 nuclear magnetic resonance spectroscopy. Tetrahedron Lett. 2015, 56 (42), 5795-5798.

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
3595854
Code tarifaire harmonisé
2930.90
TSCA
Yes
RTECS
WS3585000

Recommandé

  • A11806

    Nitromethane, 98+%
  • A12646

    Triethylamine, 99%
  • 36292

    Acetic anhydride, ACS, 97+%
  • 36560

    Tetraethylammonium hydroxide, 35% w/w aq. soln.
  • 43023

    Tetraethylammonium hydroxide, 35% w/w aq. soln., Reagent Grade

Consulté récemment

Produits chimiques

Sciences de la vie

Métaux et matériaux

Catalyseurs

Analytique et matériel de laboratoire