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7677-24-9 - Trimethylsilyl cyanide, 97% - Cyanotrimethylsilane - TMSCN - A19598 - Alfa Aesar

A19598 Trimethylsilyl cyanide, 97%

Numéro de CAS
7677-24-9
Synonymes
Cyanotrimethylsilane
TMSCN

Conditionnement Prix ($) Quantité Disponibilité
5g 41,50
25g 122,00
100g 380,00
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Trimethylsilyl cyanide, 97%

MDL
MFCD00001765
EINECS
231-657-3

Propriétés chimiques

Formule
C4H9NSi
Poids moleculaire
99.21
Point de fusion
11-12°
Point d'ébullition
118-119°
Point d'éclair
1°(33°F)
Densité
0.783
Indice de réfraction
1.3910
Sensibilité
Moisture Sensitive
Solubilité
Miscible with organic solvents.

Applications

Trimethylsilyl Cyanide is used as a reagent in the preparation of optically active cyanohydrins. It is used in the derivatization of complex metabolite mixtures by GC-MS. It is employed in the preparation of Reissert compounds, which represent reactive polyamides. Further, it is used to convert pyridine-N-oxides into 2-cyanopyridine. It is also used as a cyanide source in an enantioselective organocatalytic Strecker-type reaction of aliphatic N,N-dialkylhydrazones. In addition to this, it is used as a reagent for the cyanosilylation of aldehydes.

Notes

Moisture sensitive. Store in a cool place.Incompatible with water, strong oxidizing agents, strong reducing agents, strong acids and strong bases.

Références bibliographiques

Reagent for the formation of O-TMS cyanohydrins from carbonyl compounds.

The ZnI2-catalyzed procedure allows cyanohydrins of unreactive ketones to be prepared in good yield, avoiding the unfavourable equilibria often encountered with the classical alkali cyanide method. For details and list of examples, see: Org. Synth. Coll., 7, 20 (1990). Other catalysts including Et3N or Bu3P are also effective: Chem. Lett., 537, 541 (1991). For catalysis by Methyl­ triphenyl­phosphonium iodide, A15644 , see: Tetrahedron Lett., 44, 6157 (2003). In the absence of a catalyst, aldehydes have been found to give good yields of the TMS cyanohydrin, but reaction with ketones is very slow: J. Chem. Soc., Perkin 1, 2383 (1995). For use of Tetracyanoethyl­ene, A13945 , as a ã-acid catalyst for both aldehydes and ketones, see: J. Chem. Soc., Perkin 1, 2155 (1995). Under the same conditions, dimethyl acetals give O-methyl cyanohydrins.

For examples of transformations of ketone TMS cyanohydrins, see: Chem. Pharm. Bull., 43, 1294 (1995).

For use in asymmetric Strecker synthesis of chiral amino acids, see: Tetrahedron Lett., 29, 4397 (1988).

Tertiary alkyl halides normally undergo elimination when treated with alkali cyanides, but can be converted to the corresponding nitriles by reaction with TMSCN in the presence of SnCl4: Angew. Chem. Int. Ed., 20, 117 (1981).

Reacts with epoxides in the presence of ZnI2 to give trans-ɑ-siloxy isocyanides, which can be readily hydrolyzed to the hydroxy isocyanides: J. Am. Chem. Soc., 104, 5849 (1982); Org. Synth. Coll., 7, 294 (1990). In the presence of Ag salts (AgClO4, AgBF4 or AgOTf), alkenes can be converted to isocyanides in Markovnikov fashion: Synlett, 288 (1999).

For a brief survey of uses of this reagent in synthesis, see: Synlett, 1625 (2007).

Satoh, Y.; Obora, Y. Synthesis of arylacetonitrile derivatives: Ni-catalyzed reaction of benzyl chlorides with trimethylsilyl cyanide under base-free conditions. RSC Adv. 2014, 4 (30), 15736-15739.

Xu, W. B.; Xu, Q. H.; Zhang, Z. F.; Li, J. Z. Copper(I)-Oxide-Mediated Cyanation of Arenediazonium Tetrafluoroborates with Trimethylsilyl Cyanide: A Method for Synthesizing Aromatic Nitriles. Asian J. Org. Chem. 2015, 3 (10), 1062-1065.

Mentions de danger et de prudence du SGH

Mentions de danger (UE): H225-H300-H310-H330

Highly flammable liquid and vapour. Fatal if swallowed. Fatal in contact with skin. Fatal if inhaled.

Mentions de prudence: P301+P310a-P303+P361+P353-P304+P340-P320-P330-P405-P501a

IF SWALLOWED: Immediately call a POISON CENTER/doctor IF ON SKIN (or hair): Remove/Take off immediately all contaminated clothing. Rinse skin with water/shower. IF INHALED: Remove to fresh air and keep at rest in a position comfortable for breathing. Specific treatment is urgent (see label). Rinse mouth. Store locked up. Dispose of contents/container in accordance with local/regional/national/international regulations.

Autres références

Beilstein
1737612
Classe de danger
6.1
Groupe d'emballage
I
Code tarifaire harmonisé
2931.90
TSCA
Yes

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