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16029-98-4 - Iodotrimethylsilane, 97%, stab. with copper - TMS iodide - Trimethyliodosilane - A12902 - Alfa Aesar

A12902 Iodotrimethylsilane, 97%, stab. with copper

Numéro de CAS
16029-98-4
Synonymes
TMS iodide
Trimethyliodosilane

Conditionnement Prix ($) Quantité Disponibilité
5g 32,30
25g 86,40
100g 259,00
250g 606,00
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Iodotrimethylsilane, 97%, stab. with copper

MDL
MFCD00001028
EINECS
240-171-0

Propriétés chimiques

Formule
C3H9ISi
Poids moleculaire
200.09
Point d'ébullition
105-106°
Point d'éclair
-2°(28°F)
Densité
1.440
Indice de réfraction
1.4760
Sensibilité
Moisture & Light Sensitive
Solubilité
Miscible with water.

Applications

Iodotrimethylsilane is used for the introduction of trimethylsilyl group in organic synthesis. It is also useful for gas chromatography analysis by converting alcohol into a silyl ether derivative, thereby making it more volatile than the original molecule.

Notes

Moisture and light Sensitive. Incompatible withstrong acids, strong bases, strong oxidizing agents and reacts violently with water.

Références bibliographiques

Reactive silylating agent for conversion of ketones to silyl enol ethers (see Appendix 4). In triethylamine, the rate of silyl enol ether formation by TMS iodide is 7x109 times faster than with TMS chloride: Liebigs Ann. Chem., 1718 (1980). In combination with Hexamethyl­disilazane, A15139, unsymmetrical ketones give the thermodynamically more stable isomer: Synthesis, 730 (1979).

Valuable reagent for the mild cleavage of dialkyl and aralkyl ethers: J. Org. Chem., 42, 3761 (1977).

Alcohols are converted to alkyl iodides: Tetrahedron Lett., 2659 (1977). ɑɑ-Diaryl alcohols are reduced to the corresponding alkanes: Tetrahedron, 51, 11043 (1995); Synth. Commun., 26, 101 (1996).

Effective reagent for the O-alkyl cleavage of carboxylic esters: J. Am. Chem. Soc., 99, 968 (1977). The reaction can be catalyzed by iodine: J. Org. Chem., 44, 2185 (1979).

Catalyzes the transesterification of esters, even those of hindered acids: Synthesis, 142 (1981).

Alkyl carbamates are cleaved to amines, via the TMS esters: J. Chem. Soc., Chem. Commun., 315 (1978); for application to cleavage of N-Cbz and N-Boc groups, see: J. Chem. Soc., Chem. Commun., 495 (1979).

Catalyst for the protection of alcohols, under mild neutral conditions, as MOM ethers by trans-acetalization with Dimethoxymethane, A12055: Synthesis, 896 (1983), and as THP ethers by acetalization with dihydropyran: Synthesis, 703 (1985).

Catalyst for Michaelis-Arbuzov rearrangement of trivalent organophosphorus P-O-R compounds to the corresponding P=O derivatives, effective at lower temperatures than bromotrimethylsilane: Org. Lett., 5, 1661 (2003).

For reviews of the use of iodotrimethylsilane in organic synthesis, see: Synthesis, 861 (1980); Tetrahedron, 38, 2225 (1982); Adv. Silicon Chem., 1, 1 (1991).

Sato, A. H.; Ohashi, K.; Iwasawa, T. Regio-and stereospecific synthesis of (E)-alpha-iodoenamide moieties from ynamides through iodotrimethylsilane-mediated hydroiodation. Tetrahedron Lett. 2013, 54 (10), 1309-1311.

Sato, A. H.; Mihara, S.; Iwasawa, T. One-step synthesis of (1-iodovinyl) arenes from trimethylsilyl ethynylarene through iodotrimethylsilane-mediated hydroiodation. Tetrahedron Lett. 2012, 53 (28), 3585-3589.

Mentions de danger et de prudence du SGH

Mentions de danger (UE): H225-H314-H318

Highly flammable liquid and vapour. Causes severe skin burns and eye damage. Causes serious eye damage.

Mentions de prudence: P210-P260u-P303+P361+P353-P305+P351+P338-P405-P501a

Keep away from heat/sparks/open flames/hot surfaces. - No smoking. IF ON SKIN (or hair): Remove/Take off immediately all contaminated clothing. Rinse skin with water/shower. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. Store locked up. Dispose of contents/container in accordance with local/regional/national/international regulations.

Autres références

Beilstein
1731136
Classe de danger
3
Groupe d'emballage
II
Code tarifaire harmonisé
2931.90
TSCA
Yes

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Catalyseurs

Analytique et matériel de laboratoire