Cookies disclaimer

Estoy de acuerdo utilizamos cookies para mejorar la experiencia de navegación del usuario y para estudiar cómo se utiliza nuestro sitio web. si navega por nuestro sitio web, estará aceptando el uso de las cookies en las condiciones establecidas en la presente política de cookies. esta política puede ser actualizada, por lo que le invitamos a revisarla de forma regular

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

A12856 (Trimethylsilyl)acetylene, 98%

Número CAS
1066-54-2
Nombre Alternativo
Ethynyltrimethylsilane
TMS acetylene

Tamaño Precio ($) Cantidad Disponibilidad
5g 36,70
25g 157,00
100g 408,00
Añadir al carrito Añadir al presupuesto al por mayor Ver artículo

(Trimethylsilyl)acetylene, 98%

MDL
MFCD00008569
EINECS
213-919-9

Propiedades químicas

Fórmula
C5H10Si
Peso molecular
98.22
Punto de ebullición
52-53°
Punto de inflamabilidad
<-34°(-29°F)
Densidad
0.710
Índice de refracción
1.3900
Solubilidad
Miscible with organic solvents.

Aplicaciones

(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.

Notas

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

Referencias documentales

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. 2015, 5 (92), 75263-75267.

Wang, H.; Olesik, S. V. Development of a new separation media using ultra-thin glassy carbon film modified silica. 2015, 1379, 56-64.

Indicaciones de peligro y de precaución del GHS

Indicaciones de peligro (UE): H225

Highly flammable liquid and vapour.

Indicaciones de precaución: P210-P280-P240-P241-P233-P242-P243-P303+P361+P353-P403+P235-P501a

Keep away from heat/sparks/open flames/hot surfaces. - No smoking. Wear protective gloves/protective clothing/eye protection/face protection. Ground/bond container and receiving equipment. Use explosion-proof electrical/ventilating/lighting/ equipment. Keep container tightly closed. Use only non-sparking tools. Take precautionary measures against static discharge. IF ON SKIN (or hair): Remove/Take off immediately all contaminated clothing. Rinse skin with water/shower. Store in a well-ventilated place. Keep cool. Dispose of contents/container in accordance with local/regional/national/international regulations.

Otras referencias

Beilstein
906752
Clase de peligro
3
Grupo de embalaje
II
Código de tarifa arancelaria unificado
2931.90
TSCA
Yes

Recomendado

  • A12139

    Phenylacetylene, 98+%
  • A15275

    Boron trifluoride diethyl etherate, 98+%
  • A17020

    1-Bromo-2-iodobenzene, 98+%, stab. with copper
  • 10491

    trans-Dichlorobis(triphenylphosphine)palladium(II), Pd 14.0% min
  • 43153

    Copper(I) iodide, Puratronic®, 99.998% (metals basis)

Visto recientemente

Productos químicos

Ciencias de la vida

Metales & materiales

Catalizadores

Análisis y material de laboratorio