Bis(trimethylsilyl)acetylene
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
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)
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
- F
- 10
- TSCA
- Yes
- HazardClass
- 3
- PackingGroup
- III
- HS Code
- 29310095
MSDS
- Language:English Provider:Bis(trimethylsilyl)acetylene
- Language:English Provider:SigmaAldrich
- Language:English Provider:ACROS
- Language:English Provider:ALFA
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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Bis(trimethylsilyl)acetylene(14630-40-1)Related Product Information
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