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bis(trimethylsilyl)acetylene

CAS No. 14630-40-1 | Catalog No. 655262


Synonyms
1;2-Bis(trimethylsilyl)ethyne;1;2-ethynediylbis[trimethyl-silan ;1;2-ethynediylbis[trimethyl-Silane ;2;5-Disilahex-3-yne; 2;2;5;5-tetramethyl-;Acetylene; bis(trimethylsilyl)-;Bis(trimethylsilyl)ethyne;Silane; 1;2-ethynediylbis*trimethyl-


Properties

Boiling Point 136-137 °C(lit.)
Form liquid
Melting Point 21-24 °C(lit.)

Application
BTMSA is used as starting reagent in the synthesis of functionalized 4-R-1;2-bis(trimethylsilyl)benzenes. It is also used in the synthesis of (+)-brasilenyne2 and (β-diketanato)Ag(BTMSA). It is a ligand that binds to a central metal ion (e.g. Titanium) to create a coordination complex. One of its complexes; Permethyltitanocene-bis(trimethylsilyl)acetylene; is a catalyst for the head-to-tail dimerization of 1-alkynes (e.g. 3-Penten-1-yne [P227430]).


General Description
BTMSA participates as nucleophile in Friedel-Crafts type acylations and alkylations. BTMSA undergoes rhodium catalyzed addition reaction with diarylacetylenes. It undergoes cycloaddition with 1;5-hexadiynes in the presence of CpCo(CO)2 (Cp=cyclopentadienyl) to form benzocyclobutenes. Structure of BTMSA was characterized by a centre of inversion present on triple bond (length=1.208(3)Å). TiCl4-Et2AlCl catalyzed Diels-Alder reaction of BTMSA with norbornadiene has been reported.

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