187437
Bis(trimethylsilyl)acetylene
99%
Synonym(s):
BTMSA
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About This Item
Linear Formula:
(CH3)3SiC≡CSi(CH3)3
CAS Number:
Molecular Weight:
170.40
Beilstein:
906870
EC Number:
MDL number:
UNSPSC Code:
12352100
PubChem Substance ID:
NACRES:
NA.22
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Quality Level
Assay
99%
refractive index
n20/D 1.427 (lit.)
bp
136-137 °C (lit.)
mp
21-24 °C (lit.)
density
0.752 g/mL at 25 °C (lit.)
storage temp.
2-8°C
SMILES string
C[Si](C)(C)C#C[Si](C)(C)C
InChI
1S/C8H18Si2/c1-9(2,3)7-8-10(4,5)6/h1-6H3
InChI key
ZDWYFWIBTZJGOR-UHFFFAOYSA-N
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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)Å). TiCl4-Et2AlCl catalyzed Diels-Alder reaction of BTMSA with norbornadiene has been reported.
Application
Bis(trimethylsilyl)acetylene (BTMSA) was used as starting reagent in the synthesis of functionalized 4-R-1,2-bis(trimethylsilyl)benzenes. It was also used in the synthesis of (+)-brasilenyne and (β-diketanato)Ag(BTMSA).
Signal Word
Danger
Hazard Statements
Precautionary Statements
Hazard Classifications
Eye Irrit. 2 - Flam. Liq. 2 - Skin Irrit. 2 - STOT SE 3
Target Organs
Respiratory system
Storage Class Code
3 - Flammable liquids
WGK
WGK 3
Flash Point(F)
35.6 °F - closed cup
Flash Point(C)
2 °C - closed cup
Personal Protective Equipment
dust mask type N95 (US), Eyeshields, Gloves
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Titanium-catalyzed cycloaddition-cycloreversion cascade in the reaction of norbornadiene with bis (trimethylsilyl) acetylene.
Mach K, et al.
Organometallics, 5(6), 1215-1219 (1986)
Bis (trimethylsilyl) acetylene.
Bruckmann J and Kruger C.
Acta Crystallographica Section B, Structural Science, Crystal Engineering and Materials, 53(12), 1845-1846 (1997)
Akinobu Horita et al.
Organic letters, 10(9), 1751-1754 (2008-04-10)
The addition of bis(trimethylsilyl)acetylene to diarylacetylenes proceeds efficiently and selectively in a formal anti fashion in the presence of [Rh(OH)(cod)]2/bisphosphine and phenol as catalyst and activator, respectively, accompanied by cleavage of one of the C-Si bonds to produce the corresponding
Scott E Denmark et al.
Journal of the American Chemical Society, 124(51), 15196-15197 (2002-12-19)
The first, total synthesis of (+)-brasilenyne (1) has been achieved in 19 steps from l-(S)-malic acid. The key elements of this approach are a highly diastereoselective ring-opening of a 1,3-dioxolanone with bis(trimethylsilyl)acetylene) promoted by TiCl4 to set a propargylic stereocenter
Tetrahedron Letters, 35, 417-417 (1994)
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