117706

Sigma-Aldrich

Phenylacetylene

98%

Synonym(s):
Ethynylbenzene
Linear Formula:
C6H5CCH
CAS Number:
Molecular Weight:
102.13
Beilstein/REAXYS Number:
605461
MDL number:
PubChem Substance ID:
NACRES:
NA.22

vapor pressure

17.6 mmHg ( 37.7 °C)

Quality Level

assay

98%

impurities

<1% 1,4-dioxane

refractive index

n20/D 1.549 (lit.)

bp

142-144 °C (lit.)

solubility

H2O: insoluble
alcohol: miscible
diethyl ether: miscible

density

0.93 g/mL at 25 °C (lit.)

storage temp.

2-8°C

SMILES string

C#Cc1ccccc1

InChI

1S/C8H6/c1-2-8-6-4-3-5-7-8/h1,3-7H

InChI key

UEXCJVNBTNXOEH-UHFFFAOYSA-N

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General description

Phenylacetylene undergoes polymerization catalyzed by Rh and Pt complexes to form polyphenylacetylene.

Application

Terminal acetylene used in the conversion of nitrones to alkynyl hydroxyl amines in the presence of trimethylaluminum..
Phenylacetylene was used in a study to investigate the mechanism of product formation during the palladium-catalysed phenylacetylene oxidative carbonylation reaction.

Packaging

25, 100 mL in glass bottle

Pictograms

FlameExclamation mark

Signal Word

Warning

Hazard Statements

Target Organs

Respiratory system

Personal Protective Equipment

dust mask type N95 (US),Eyeshields,Gloves

RIDADR

UN 3295C 3 / PGIII

WGK Germany

WGK 3

Flash Point(F)

80.6 °F - closed cup

Flash Point(C)

27 °C - closed cup

Certificate of Analysis

Certificate of Origin

Tetrahedron Letters, 48, 1457-1457 (2007)
Rhodium and platinum complexes as catalysts for the polymerization of phenylacetylene.
Furlani A, et al.
Journal of Polymer Science Part A: Polymer Chemistry, 24(5), 991-1005 (1986)
Katarina Novakovic et al.
Physical chemistry chemical physics : PCCP, 10(5), 749-753 (2008-02-07)
This paper reports on the influence of oscillations on product selectivity as well as the dynamics of product formation during the palladium-catalysed phenylacetylene oxidative carbonylation reaction in a catalytic system (PdI2, KI, Air, NaOAc in methanol). The occurrence of the...
Kyoung Chul Ko et al.
The journal of physical chemistry. A, 116(25), 6837-6844 (2012-06-06)
The intramolecular magnetic coupling constant (J) values of diradical systems linked with two monoradicals through a coupler (para-substituted phenyl acetylene (Model I), meta-substituted phenyl acetylene (Model II), ethylene (Model III)) were investigated by unrestricted density functional theory calculations. We divided...
Zhuofeng Ke et al.
Journal of the American Chemical Society, 134(37), 15418-15429 (2012-09-13)
Artificial metalloenzyme, composed of metal complex(es) and a host protein, is a promising way to mimic enzyme catalytic functions or develop novel enzyme-like catalysis. However, it is highly challenging to unveil the active site and exact reaction mechanism inside artificial...
Articles
The terminal alkyne functionality has a wide range of applications including most recently the synthesis of spiropyran substituted 2,3-dicyanopyrazines and (±)-asteriscanolide, as well as conversion to enamines using resin-bound 2° amines.
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