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Sigma-Aldrich

(tert-Butyldimethylsilyl)acetylene

99%

Synonym(s):

Ethynyl-tert-butyldimethylsilane

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About This Item

Linear Formula:
(CH3)3CSi(CH3)2C≡CH
CAS Number:
86318-61-8
Molecular Weight:
140.30
Beilstein:
1921466
MDL number:
MFCD00191877
UNSPSC Code:
12352100
PubChem Substance ID:
24864798
NACRES:
NA.22

Quality Level

100

Assay

99%

refractive index

n20/D 1.451 (lit.)

bp

116-117 °C (lit.)

density

0.751 g/mL at 25 °C (lit.)

SMILES string

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

InChI

1S/C8H16Si/c1-7-9(5,6)8(2,3)4/h1H,2-6H3

InChI key

RTYNRTUKJVYEIE-UHFFFAOYSA-N

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General description

(tert-Butyldimethylsilyl)acetylene is a bulky trialkylsilyl-protected alkyne. It participates in Cadiot-Chodkiewicz cross-coupling reaction with various bromoalkynes to afford synthetically useful unsymmetrical diynes.
(tert-Butyldimethylsilyl)acetylene readily undergoes cross-dimerization reaction with various internal phenyl acetylenes in the presence of rhodium dimers and bidentate phosphine ligands to afford enynes.

Application

(tert-Butyldimethylsilyl)acetylene may be used in the synthesis of β-alkynylketone and β-alkynyl aldehydes.

accessory

Product No.
Description
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Pictograms

Flame
GHS02

Signal Word

Danger

Hazard Statements

H225

Precautionary Statements

P210

Hazard Classifications

Flam. Liq. 2

Storage Class Code

3 - Flammable liquids

WGK

WGK 3

Flash Point(F)

42.8 °F - closed cup

Flash Point(C)

6 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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Trost BM and Li CJ.
Modern Alkyne Chemistry: Catalytic and Atom-Economic Transformations (2014)
Joseph P Marino et al.
The Journal of organic chemistry, 67(19), 6841-6844 (2002-09-14)
Bulky trialkylsilyl-protected alkynes such as triethylsilyl (TES), tert-butyldimethylsilyl (TBS), and triisopropylsilyl (TIPS) acetylenes underwent the Cadiot-Chodkiewicz cross-coupling reaction with different bromoalkynes to form a variety of synthetically useful unsymmetrical diynes in good yields. The diyne alcohol 10 was transformed regio-
Asymmetric synthesis of beta-alkynyl aldehydes by rhodium-catalyzed conjugate alkynylation.
Takahiro Nishimura et al.
Angewandte Chemie (International ed. in English), 48(43), 8057-8059 (2009-09-22)
Steric tuning of silylacetylenes and chiral phosphine ligands for rhodium-catalyzed asymmetric conjugate alkynylation of enones.
Takahiro Nishimura et al.
Journal of the American Chemical Society, 130(5), 1576-1577 (2008-01-17)

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