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117706

Sigma-Aldrich

Phenylacetylene

98%

Synonym(s):

Ethynylbenzene

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About This Item

Linear Formula:
C6H5CCH
CAS Number:
536-74-3
Molecular Weight:
102.13
Beilstein:
605461
MDL number:
MFCD00008570
UNSPSC Code:
12352100
PubChem Substance ID:
24847341
NACRES:
NA.22

vapor pressure

17.6 mmHg ( 37.7 °C)

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..

Signal Word

Danger

Hazard Statements

H226,H314,H350,H412

Hazard Classifications

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

Storage Class Code

3 - Flammable liquids

WGK

WGK 3

Flash Point(F)

80.6 °F - closed cup

Flash Point(C)

27 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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)
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
Akira Onoda et al.
Chemical communications (Cambridge, England), 48(78), 9756-9758 (2012-08-25)
Our group recently prepared a hybrid catalyst containing a rhodium complex, Rh(Cp)(cod), with a maleimide moiety at the peripheral position of the Cp ligand. This compound was then inserted into a β-barrel protein scaffold of a mutant of aponitrobindin (Q96C)
Simon Rondeau-Gagné et al.
Journal of the American Chemical Society, 135(1), 110-113 (2012-12-20)
Soluble organic nanorods were prepared from phenylacetylene macrocycles using the topochemical polymerization of butadiyne moieties placed both inside and outside the macrocycles' skeletons. Macrocycles containing amide groups were self-assembled in a columnar fashion through the formation of an organogel in
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