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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
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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.[1]
  • Glycosylated oligo(ethynylene)s using the Negishi reaction.[2]
  • (±) Falcarinol, a polyacetylene class of fatty alcohol.[3]

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

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Certificates of Analysis (COA)

Lot/Batch Number
0000346582
0000346581
0000315606
0000346582
0000346581

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Tobias N Hoheisel et al.
Organic letters, 10(20), 4525-4528 (2008-09-25)
A convenient and efficient sp-sp carbon heterocoupling protocol based on the Negishi reaction was developed, in which the required zinc diacetylide was generated from 1,4-bis(trimethylsilyl)butadiyne in situ and reacted with a bromoacetylene in apolar solvent mixtures. The method has been
A convenient Negishi protocol for the synthesis of glycosylated oligo (ethynylene) s
Hoheisel TN and Frauenrath H
Organic Letters, 10, 4525-4528 (2008)
Hydrosilylation of 1, 4-bis (trimethylsilyl) butadiyne and silyl-substituted butenynes
Kusumoto T, et al.
Bulletin of the Chemical Society of Japan, 65, 1280-1290 (1992)
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
A short synthesis of (+) and (-)-falcarinol
McLaughlin NP, et al.
Tetrahedron, 66, 9681-9687 (2010)
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