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263567

Sigma-Aldrich

1,4-Bis(trimethylsilyl)butadiyne

98%, stable crystalline form of butadiyne

Synonym(s):

1,4-Bis(trimethylsilyl)-1,3-butadiyne, BTMSBD

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About This Item

Linear Formula:
(CH3)3SiC≡CC≡CSi(CH3)3
CAS Number:
4526-07-2
Molecular Weight:
194.42
Beilstein:
1758268
MDL number:
MFCD00009839
UNSPSC Code:
12352100
PubChem Substance ID:
24855983
NACRES:
NA.22

Assay

98%

form

solid

refractive index

n20/D 1.384 (lit.)

mp

111-113 °C (lit.)

density

0.974 g/mL at 20 °C (lit.)

storage temp.

2-8°C

SMILES string

C[Si](C)(C)C#CC#C[Si](C)(C)C

InChI

1S/C10H18Si2/c1-11(2,3)9-7-8-10-12(4,5)6/h1-6H3

InChI key

LBNVCJHJRYJVPK-UHFFFAOYSA-N

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Application

1,4-Bis(trimethylsilyl)butadiyne can be used as a reagent to prepare:
  • 1,1,3,4-Tetrasilyl-substituted 1,3-butadienes or 1,1,3,4-tetrasilyl-substituted 1,2-butadienes by hydrosilylation reaction using various hydridosilanes and catalysts.
  • Glycosylated oligo(ethynylene)s using the Negishi reaction.
  • (±) Falcarinol, a polyacetylene class of fatty alcohol.

Pictograms

Flame
GHS02

Signal Word

Danger

Hazard Statements

H228

Precautionary Statements

P210

Hazard Classifications

Flam. Sol. 1

Storage Class Code

4.1B - Flammable solid hazardous materials

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Hydrosilylation of 1, 4-Bis (trimethylsilyl) butadiyne and Silyl-Substituted Butenynes.
Kusumoto T, et al.
Bulletin of the Chemical Society of Japan, 65(5), 1280-1290 (1992)
A short synthesis of (+) and (-)-falcarinol
McLaughlin NP, et al.
Tetrahedron, 66, 9681-9687 (2010)
Manuel M Bentlohner et al.
Angewandte Chemie (International ed. in English), 54(12), 3748-3753 (2015-02-04)
The accessibility of triads with deltahedral Zintl clusters in analogy to fullerene-linker-fullerene triads is another example for the close relationship between fullerenes and Zintl clusters. The compound {[K(2.2.2-crypt)]4[RGe9-CH=CH-CH=CH-Ge9R]}(toluene)2 (R=(2Z,4E)-7-amino-5-aza-hepta-2,4-dien-2-yl), containing two deltahedral [Ge9] clusters linked by a conjugated (1Z,3Z)-buta-1,3-dien-1,4-diyl bridge
Manuel M Bentlohner et al.
Chemistry (Weinheim an der Bergstrasse, Germany), 23(67), 17089-17094 (2017-09-15)
We report on the synthesis and structure, as well as on the mechanism of formation of the [Ge
A convenient Negishi protocol for the synthesis of glycosylated oligo (ethynylene) s
Hoheisel TN and Frauenrath H
Organic Letters, 10, 4525-4528 (2008)
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