Phenylacetylene Chemical Properties

Melting point:

-44.8 °C

Boiling point:

142-144 °C (lit.)

Density 

0.93 g/mL at 25 °C (lit.)

vapor pressure 

17.6 mm Hg ( 37.7 °C)

refractive index 

n20/D 1.549(lit.)

Flash point:

88 °F

storage temp. 

Store at +2°C to +8°C.

solubility 

H2O: insoluble

pka

19(at 25℃)

form 

Liquid

color 

Clear colorless to yellow

Specific Gravity

0.930

Water Solubility 

INSOLUBLE

Sensitive 

Light Sensitive

Merck 

14,3861

BRN 

605461

Dielectric constant

3.0（20℃）

Stability:

Stable. Flammable. Incompatible with strong oxidizing agents, acids, halogens.

CAS DataBase Reference

536-74-3(CAS DataBase Reference)

NIST Chemistry Reference

Phenylacetylene(536-74-3)

EPA Substance Registry System

Phenylacetylene (536-74-3)

Safety Information

Hazard Codes 

Xn

Risk Statements 

10-36/37/38-40-65-36/37

Safety Statements 

16-26-36/37/39-45-62-36/37

RIDADR 

UN 3295 3/PG 3

WGK Germany 

1

RTECS 

DA0780000

F 

8-19

TSCA 

Y

HS Code 

2902 90 00

HazardClass 

3

PackingGroup 

III

MSDS

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• Language:English Provider:SigmaAldrich
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Phenylacetylene Usage And Synthesis

Synthesis

It is suitable for the synthesis of Terminal Alkynes by the reaction of substituted benzaldehyde with alkali. 2-bromovinyl benzene can be obtained by reacting 2,3-dibromo-3-phenylpropionic acid with base and triethylamine in DMF, and then it can be directly reacted with potassium hydroxide to obtain the desired product Phenylacetylene.

Description

Phenylacetylene is an alkyne hydrocarbon containing a phenyl group. It exists as a colorless, viscous liquid. In research, it is sometimes used as an analog for acetylene; being a liquid, it is easier to handle than acetylene gas.
Phenylacetylene undergoes polymerization catalyzed by Rh and Pt complexes to form polyphenylacetylene.

Chemical Properties

colourless liquid

Uses

Ethynylbenzene, an aromatic hydrocarbon, is important in the petrochemical industry as an intermediate in the production of styrene, which in turn is used for making polystyrene, a common plastic mate rial.

Uses

Phenylacetylene is involved in the preparation of styrene by reduction using Lindlar catalyst. It is used to study the mechanism of the palladium-catalyzed phenyl acetylene oxidative carbonylation reaction. It is also used in the polymerization process to prepare polyphenylacetylene namely 1,2,4-triphenylbenzene and 1,3,5-triphenylbenzene.

Uses

Terminal acetylene used in the conversion of nitrones to alkynyl hydroxyl amines in the presence of trimethylaluminum..

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.

Definition

ChEBI: Ethynylbenzene is a member of benzenes.

Synthesis Reference(s)

Journal of the American Chemical Society, 89, p. 4487, 1967 DOI: 10.1021/ja00993a043

General Description

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

Flammability and Explosibility

Flammable

Purification Methods

Distil phenylacetylene through a spinning band column. It should be filtered through a short column of alumina before use [Collman et al. J Am Chem Soc 108 2988 1986; for pK see Brandsma Preparative Acetylenic Chemistry, 1st Edn Elsevier 1971, p. 15, ISBN 0444409475]. [Beilstein 5 IV 1525.]

Precautions

Store in cool place. Moisture sensitive. Keep the container tightly closed in a dry and well-ventilated place. Incompatible with acids, halogens, alkali metals and oxidizing agents.

Phenylacetylene(536-74-3)Related Product Information

• Acetylene
• Acetophenone
• Phenylacetaldehyde
• 4-Hydrazinobenzenesulfonic acid
• Phenylhydrazine hydrochloride
• Phenylmalonic acid
• Phenylacetyl chloride
• Phenylhydrazine
• 4-Ethynyltoluene
• Diphenylacetylene
• 3-Ethynylaniline
• 1-ETHYL-2-PHENYLACETYLENE
• 9,10-Bis(phenylethynyl)anthracene
• Phenylacetylene monocarboxylic acid
• 4-(Trans-4-propylcyclohexyl) phenylacetylene
• 2-(TRIFLUOROMETHYL)PHENYLACETYLENE
• 1-METHYL-2-PHENYLACETYLENE
• 3-FLUORO-4-(TRIFLUOROMETHOXY)PHENYLACETYLENE