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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/REAXYS Number:
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

signalword

Danger

hcodes

H228

pcodes

P210

Hazard Classifications

Flam. Sol. 1

Storage Class

4.1B - Flammable solid hazardous materials

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type P3 (EN 143) respirator cartridges

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Certificates of Analysis (COA)

Lot/Batch Number
1439888V
BGBC2598V
BGBC0932V
1439888
1403224

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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
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 short synthesis of (+) and (-)-falcarinol
McLaughlin NP, et al.
Tetrahedron, 66, 9681-9687 (2010)
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)

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