Synthesis
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Phenylacetylene

Synthesis
Product Name
Phenylacetylene
CAS No.
536-74-3
Chemical Name
Phenylacetylene
Synonyms
Ethynylbenzene;Phenylethyne;phenylacetylide;1-Phenylethyne;Benzene, ethynyl-;Phenylacetylene, pure, 98%;ethyne,phenyl-;Ethynylbenaene;ethynyl-benzen;Ethinylbenzene
CBNumber
CB9853753
Molecular Formula
C8H6
Formula Weight
102.13
MOL File
536-74-3.mol
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Phenylacetylene Property

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)
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Safety

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
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Danger
Hazard statements

H226Flammable liquid and vapour

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

H350May cause cancer

Precautionary statements

P202Do not handle until all safety precautions have been read and understood.

P210Keep away from heat/sparks/open flames/hot surfaces. — No smoking.

P233Keep container tightly closed.

P303+P361+P353IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

P308+P313IF exposed or concerned: Get medical advice/attention.

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
8.07044
Product name
Phenylacetylene
Purity
for synthesis
Packaging
25ML
Price
$45.6
Updated
2024/03/01
Sigma-Aldrich
Product number
8.07044
Product name
Phenylacetylene
Purity
for synthesis
Packaging
100ML
Price
$158
Updated
2024/03/01
Sigma-Aldrich
Product number
117706
Product name
Phenylacetylene
Purity
98%
Packaging
25ml
Price
$52.8
Updated
2024/03/01
Sigma-Aldrich
Product number
117706
Product name
Phenylacetylene
Purity
98%
Packaging
100ml
Price
$162
Updated
2024/03/01
TCI Chemical
Product number
E0196
Product name
Ethynylbenzene
Purity
>98.0%(GC)
Packaging
25mL
Price
$50
Updated
2024/03/01
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Phenylacetylene Chemical Properties,Usage,Production

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 Preparation Products And Raw materials

Raw materials

beta-Bromostyrene

Preparation Products

5-(2-PHENYLETH-1-YNYL)THIOPHENE-2-CARBALDEHYDE polyphenylene (III) PPV 4-PHENYLETHYNYLPHTHALIC ANHYDRIDE Diphenylacetylene E-PHENYLETHENYLBORONIC ACID 1,2-NAPHTHALIC ANHYDRIDE 4-Phenylpiperidine
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View Lastest Price from Phenylacetylene manufacturers

Chemwill Asia Co.,Ltd.
Product
Phenylacetylene 536-74-3 Ethynylbenzene 536-74-3
Price
US $9.95/KG
Min. Order
1KG
Purity
99.50% IN STOCK
Supply Ability
500 MT per month
Release date
2019-09-03
Chemwill Asia Co.,Ltd.
Product
536-74-3 Phenylacetylene 536-74-3
Price
US $15.50/KG
Min. Order
1KG
Purity
99.50% IN STOCK
Supply Ability
500 MT per month
Release date
2019-09-03
Chemwill Asia Co.,Ltd.
Product
Phenylacetylene 536-74-3
Price
US $6.55/KG
Min. Order
1KG
Purity
99.50% IN STOCK
Supply Ability
680 MT per month
Release date
2019-09-03

536-74-3, PhenylacetyleneRelated Search:

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

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  • bc0001