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187437

Sigma-Aldrich

Bis(trimethylsilyl)acetylene

99%

Synonym(s):

BTMSA

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About This Item

Linear Formula:
(CH3)3SiC≡CSi(CH3)3
CAS Number:
14630-40-1
Molecular Weight:
170.40
Beilstein:
906870
EC Number:
238-671-9
MDL number:
MFCD00008276
UNSPSC Code:
12352100
PubChem Substance ID:
24851275
NACRES:
NA.22

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).

Pictograms

FlameExclamation mark
GHS02,GHS07

Signal Word

Danger

Hazard Statements

H225,H315,H319,H335

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

Certificates of Analysis (COA)

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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)
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
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
Tetrahedron Letters, 35, 417-417 (1994)
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Articles

Diels–Alder Reaction

The Diels–Alder reaction is the reaction between a conjugated diene and an alkene (dienophile) to form unsaturated six-membered rings. It is also referred to as a cycloaddition.

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