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Bis(trimethylsilyl)acetylene

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Bis(trimethylsilyl)acetylene Basic information

Product Name:
Bis(trimethylsilyl)acetylene
Synonyms:
  • BIS(TRIMETHYLSILYL)ACETYLENE
  • BSTMA
  • BTMSA
  • Bis(trimethylsilyl)acetylene 99%
  • 1,2-BIS-TRIMETHYLSILANYL-ETHYNE
  • TIMTEC-BB SBB008997
  • ICLA-002
  • 1,2-Bis(trimethylsilyl)acetylene
CAS:
14630-40-1
MF:
C8H18Si2
MW:
170.4
EINECS:
238-671-9
Product Categories:
  • Alkynes
  • Building Blocks
  • organosilicon compounds
  • Chemical Synthesis
  • Internal
  • Organic Building Blocks
  • Industrial/Fine Chemicals
  • Acetylenes
  • Ethynylsilanes
  • Functionalized Acetylenes
  • Si (Classes of Silicon Compounds)
  • Si-(C)4 Compounds
  • Silicon Compounds (for Synthesis)
  • Synthetic Organic Chemistry
Mol File:
14630-40-1.mol
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Bis(trimethylsilyl)acetylene Chemical Properties

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
Specific Gravity
0.770
color 
colorless
Water Solubility 
MAY DECOMPOSE
Hydrolytic Sensitivity
2: reacts with aqueous acid
BRN 
906870
InChIKey
ZDWYFWIBTZJGOR-UHFFFAOYSA-N
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)
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Safety Information

Hazard Codes 
F,Xi
Risk Statements 
11-36/37/38-10
Safety Statements 
16-26-36
RIDADR 
UN 1993 3/PG 2
WGK Germany 
3
10
TSCA 
Yes
HazardClass 
3
PackingGroup 
III
HS Code 
29310095

MSDS

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Bis(trimethylsilyl)acetylene Usage And Synthesis

Chemical Properties

clear colorless liquid after melting

Uses

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

Uses

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]).

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.]

Bis(trimethylsilyl)acetylene Preparation Products And Raw materials

Raw materials

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