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1066-54-2 - (Trimethylsilyl)acetylene, 98% - Ethynyltrimethylsilane - TMS acetylene - A12856 - Alfa Aesar

A12856 (Trimethylsilyl)acetylene, 98%

Codice CAS
1066-54-2
Sinonimi
Ethynyltrimethylsilane
TMS acetylene

Dimensioni Prezzo ($) Quantità Disponibilità
5g 36,70
25g 157,00
100g 408,00
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(Trimethylsilyl)acetylene, 98%

MDL
MFCD00008569
EINECS
213-919-9

Proprietà chimiche

Formula
C5H10Si
Peso formula
98.22
Punto di ebollizione
52-53°
Punto di infiammabilità
<-34°(-29°F)
Densità
0.710
Indice di rifrazione
1.3900
Solubilità
Miscible with organic solvents.

Applicazioni

(Trimethylsilyl)acetylene is used in the preparation of trimethylsilanyl-propiolic acid ethyl ester by reacting with carbonochloridic acid ethyl ester as well as in the synthesis of iodoalkenes by radical addition of perfluoroalkyl iodides. It is used as a nucleophile in Friedel-Crafts type acylations and alkylations reactions, as a ligand in organometallic chemistry and an useful reagent in cycloaddition reactions. It acts as a precursor to lithium trimethylsilylacetylide It finds application in the synthesis of (±)-estrone.

Note

Store in a cool place. Incompatible with strong oxidizing agents.

Letteratura

Pd catalyzed coupling with aryl bromides or iodides gives aryl TMS alkynes, from which the TMS group is readily cleaved by K2CO3 in MeOH: Synthesis, 627 (1980); J. Org. Chem., 46, 2280 (1981). Coupling with 1-bromo-2-nitrobenzene or ethyl 2-bromocarbanilate gives indole precursors. Other terminal alkynes lead to 2-substituted indoles: Heterocycles, 24, 31 (1986):

Cross-coupling with aryl halides can also be catalyzed by Pd-C in the presence of Ph3P, CuI and Et3N: Synth. Commun., 20, 2059 (1990); for an example, see 2-Bromonaphthalene, A15300. Pd catalyzed coupling with quinolinol and isoquinolinol triflates has also been reported: Tetrahedron, 51, 3737 (1995). For coupling with vinyl halides catalyzed by Tetrakis(triphenyl­phosphine)­palladium(0)­, 10548 in the presence of CuI as an example of a route to enynes, see: Tetrahedron Lett., 30, 6997 (1989); Org. Synth. Coll., 9, 117 (1998). CuCl-TMEDA catalyzed oxidative (Hay) coupling gives bis(TMS)-1,3-butadiyne: Org. Synth. Coll., 8, 63 (1993).

For the synthesis of iodoalkenes by radical addition of perfluoroalkyl iodides, see: J. Org. Chem., 47, 2251 (1982).

Das, S.; Samanta, S.; Ray, S.; Biswas, P. 3, 6-Di (pyridin-2-yl)-1, 2, 4, 5-tetrazine capped Pd (0) nanoparticles: a catalyst for copper-free Sonogashira coupling of aryl halides in aqueous medium. J. Chromatogr. A 2015, 1379, 56-64.

Rischio GHS e dichiarazioni precauzionali

Dichiarazioni di rischio (UE): H225

Highly flammable liquid and vapour.

Dichiarazioni precauzionali: P210-P280a-P240-P241-P303+P361+P353-P501a

Keep away from heat/sparks/open flames/hot surfaces. - No smoking. Wear protective gloves and eye/face protection. Ground/bond container and receiving equipment. Use explosion-proof electrical/ventilating/lighting/ equipment. IF ON SKIN (or hair): Remove/Take off immediately all contaminated clothing. Rinse skin with water/shower. Dispose of contents/container in accordance with local/regional/national/international regulations.

Altri riferimenti

Beilstein
906752
Classe di rischio
3
Gruppo di imballaggio
II
Codice tariffe armonizzato
2931.90
TSCA
Yes

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