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117706

Sigma-Aldrich

Phenylacetylene

98%

Sinónimos:

Ethynylbenzene

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About This Item

Fórmula lineal:
C6H5CCH
Número de CAS:
536-74-3
Peso molecular:
102.13
Beilstein/REAXYS Number:
605461
MDL number:
MFCD00008570
UNSPSC Code:
12352100
PubChem Substance ID:
24847341
NACRES:
NA.22

vapor pressure

17.6 mmHg ( 37.7 °C)

Quality Level

200

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 is an aromatic organic compound frequently employed in Sonogashira coupling reactions. Phenylacetylene undergoes polymerization catalyzed by Rh and Pt complexes to form polyphenylacetylene.

Application

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

signalword

Danger

Hazard Classifications

Aquatic Chronic 3 - Carc. 1B - Eye Dam. 1 - Flam. Liq. 3 - Skin Corr. 1B

Storage Class

3 - Flammable liquids

wgk_germany

WGK 3

flash_point_f

80.6 °F - closed cup

flash_point_c

27 °C - closed cup

ppe

Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter

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Certificados de análisis (COA)

Lot/Batch Number
BCCF2539
BCCB7908
BCBZ7343
BCBW5825
BCBT2289

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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
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)
Tetrahedron Letters, 48, 1457-1457 (2007)
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
Zhouqing Xu et al.
Chemical communications (Cambridge, England), 48(46), 5736-5738 (2012-05-09)
[8+12]-metallamacrocycle-based 3D frameworks {[Cu(4)(pbt)(2)(SO(4))(2)(DMF)(2)(CH(3)OH)]·7H(2)O·DMF}(n) (1) and [12]-macrocycle 3D {[Cu(2)(pbt)(SO(4))(DMSO)(CH(3)OH)(2)]·5H(2)O·CH(3)OH}(n) (2) have been obtained. Both complexes display antiferromagnetic couplings and high catalytic activity in the oxidative coupling reaction of 1-ethynylbenzene and oxazolidin-2-one.
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Artículos

New Aromatic Terminal Alkynes

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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