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HomeProduct name listBis(trimethylsilyl)acetylene

Bis(trimethylsilyl)acetylene

Synonym(s):BTMSA

  • CAS NO.:14630-40-1
  • Empirical Formula: C8H18Si2
  • Molecular Weight: 170.4
  • MDL number: MFCD00008276
  • EINECS: 238-671-9
  • SAFETY DATA SHEET (SDS)
  • Update Date: 2023-05-15 10:43:28
Bis(trimethylsilyl)acetylene Structural

What is Bis(trimethylsilyl)acetylene?

Chemical properties

clear colorless liquid after melting

The Uses of Bis(trimethylsilyl)acetylene

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). Bis(trimethylsilyl)acetylene 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]).

The Uses of Bis(trimethylsilyl)acetylene

In the presence of CpCo(CO)2 (cat. no. 245259), undergoes cycloaddition with 1,5-hexadiynes to form benzocyclobutenes.1

General Description

Bis(trimethylsilyl)acetylene (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)?). TiCl4-Et2AlCl catalyzed Diels-Alder reaction of BTMSA with norbornadiene has been reported.

Purification Methods

Dissolve it in pet ether and wash it with ice-cold dilute HCl. The pet ether extract is dried (MgSO4), evaporated and fractionated at 760mm. [Walton & Waugh J Organomet Chem 37 45 1972, Beilstein 4 IV 3950.]

Properties of Bis(trimethylsilyl)acetylene

Melting point: 21-24 °C(lit.)
Boiling point: 136-137 °C(lit.)
Density  0.752 g/mL at 25 °C(lit.)
refractive index  n20/D 1.427(lit.)
Flash point: 29 °C
storage temp.  2-8°C
solubility  soluble in Chloroform, Methanol
form  liquid
color  colorless
Specific Gravity 0.770
Water Solubility  MAY DECOMPOSE
Hydrolytic Sensitivity 2: reacts with aqueous acid
BRN  906870
CAS DataBase Reference 14630-40-1(CAS DataBase Reference)
NIST Chemistry Reference Silane, 1,2-ethynediylbis[trimethyl-(14630-40-1)
EPA Substance Registry System Silane, 1,2-ethynediylbis[trimethyl- (14630-40-1)

Safety information for Bis(trimethylsilyl)acetylene

Signal word Danger
Pictogram(s)
ghs
Flame
Flammables
GHS02
ghs
Exclamation Mark
Irritant
GHS07
GHS Hazard Statements H225:Flammable liquids
H315:Skin corrosion/irritation
H319:Serious eye damage/eye irritation
H335:Specific target organ toxicity, single exposure;Respiratory tract irritation
Precautionary Statement Codes P210:Keep away from heat/sparks/open flames/hot surfaces. — No smoking.
P302+P352:IF ON SKIN: wash with plenty of soap and water.
P305+P351+P338:IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

Computed Descriptors for Bis(trimethylsilyl)acetylene

InChIKey ZDWYFWIBTZJGOR-UHFFFAOYSA-N

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