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338923

1-Phenyl-2-trimethylsilylacetylene

Name: 1-Phenyl-2-trimethylsilylacetylene
Brand: ALDRICH

99%

Synonym(s):

1-(Trimethylsilyl)-2-phenylacetylene, Phenylethynyl-trimethylsilane, Trimethyl(phenylethynyl)silane

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About This Item

Linear Formula:

C₆H₅C≡CSi(CH₃)₃

CAS Number:

2170-06-1

Molecular Weight:

174.31

UNSPSC Code:

12352100

NACRES:

NA.22

PubChem Substance ID:

24860590

MDL number:

MFCD00054860

Beilstein/REAXYS Number:

3088678

Assay:

99%

Form:

liquid

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Properties

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.)

functional group

phenyl

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

Description

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

GHS07

signalword

Warning

hcodes

H315,H319,H335

pcodes

P261 - P264 - P271 - P280 - P302 + P352 - P305 + P351 + P338

Hazard Classifications

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

target_organs

Respiratory system

Storage Class

10 - Combustible liquids

wgk

WGK 3

flash_point_f

165.2 °F - closed cup

flash_point_c

74 °C - closed cup

ppe

dust mask type N95 (US), Eyeshields, Gloves

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Facile coupling of propargylic, allylic and benzylic alcohols with allylsilane and alkynylsilane, and their deoxygenation with Et3SiH, catalyzed by Bi(OTf)3 in [BMIM][BF4] ionic liquid (IL), with recycling and reuse of the IL.

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

Electro-optical and Electrochemical Properties of a Disubstituted Polyacetylene: Poly (1-phenyl-2-trimethylsilylacetylene)

Choi HK, et al.

Mol. Cryst. Liq. Cryst., 563, 153-158 (2012)

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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Global Trade Item Number

SKU	GTIN
338923-50G	04061837581106
338923-10G	04061826745649