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Sigma-Aldrich

1-Phenyl-2-trimethylsilylacetylene

99%

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Synonym(s):
1-(Trimethylsilyl)-2-phenylacetylene, Phenylethynyl-trimethylsilane, Trimethyl(phenylethynyl)silane
Linear Formula:
C6H5C≡CSi(CH3)3
CAS Number:
2170-06-1
Molecular Weight:
174.31
Beilstein:
3088678
MDL number:
MFCD00054860
UNSPSC Code:
12352100
PubChem Substance ID:
24860590
NACRES:
NA.22

Quality Level

100

Assay

99%

form

liquid

refractive index

n20/D 1.528 (lit.)

bp

87-88 °C/9 mmHg (lit.)

density

0.886 g/mL at 25 °C (lit.)

SMILES string

C[Si](C)(C)C#Cc1ccccc1

InChI

1S/C11H14Si/c1-12(2,3)10-9-11-7-5-4-6-8-11/h4-8H,1-3H3

InChI key

UZIXCCMXZQWTPB-UHFFFAOYSA-N

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General description

1-Phenyl-2-trimethylsilylacetylene is an SiMe3-substituted alkyne. It undergoes coupling with propargylic and allylic alcohols. Polymerization of 1-phenyl-2-trimethylsilylacetylene by various transition metal catalysts has been reported.

Application

1-Phenyl-2-trimethylsilylacetylene was used in the preparation of donor-stabilized Pt-η2-alkyne complexes.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H315,H319,H335

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

WGK

WGK 3

Flash Point(F)

165.2 °F

Flash Point(C)

74 °C

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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G G K S Narayana Kumar et al.
Organic & biomolecular chemistry, 10(36), 7347-7355 (2012-08-11)
Allyltrimethylsilane (allyl-TMS) reacts with propargylic alcohols 1a-1d in the presence of 10% Bi(OTf)(3) in [BMIM][BF(4)] solvent to furnish the corresponding 1,5-enynes in respectable isolated yields (87-93%) at room temperature. The utility of Bi(OTf)(3) as a superior catalyst was demonstrated in
Thermal and photochemical silicon-carbon bond activation in donor-stabilized platinum (0)-alkyne complexes.
Muller C, et al.
Organometallics, 21(6), 1190-1196 (2002)
Polymerization of 1-phenyl-2-trimethylsilylacetylene by transition metal catalysts.
Gal Y-S and Choi S-K.
Journal of Polymer Science Part A: Polymer Chemistry, 25(8), 2323-2326 (1987)

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