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536-74-3 - Phenylacetylene, 98+% - Ethynylbenzene - A12139 - Alfa Aesar

A12139 Phenylacetylene, 98+%

CAS Number
536-74-3
Synonyms
Ethynylbenzene

Size Price ($) Quantity Availability
25g 29.56
100g 92.08
500g 349.20
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Phenylacetylene, 98+%

MDL
MFCD00008570
EINECS
208-645-1

Chemical Properties

Formula
C8H6
Formula Weight
102.14
Melting point
-45°
Boiling Point
142-144°
Flash Point
27°(81°F)
Density
0.930
Refractive Index
1.5480
Sensitivity
Light Sensitive
Solubility
Immiscible with water.

Applications

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.

Notes

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.

Literature References

Conversion to the 1-bromoalkyne has been described: Org. Synth. Coll., 5, 921 (1973). For an improved phase-transfer method, using NaBr/NaOCl, see: J. Org. Chem., 57, 4555 (1992).

For cyanation with CuCN in the presence of TMS chloride and NaI, see: Tetrahedron Lett., 34, 591 (1993).

Glaser oxidative coupling by Cu(OAc)2 in pyridine gives diphenylbuta-1,3-diyne: Org. Synth. Coll., 5, 499 (1973).

For conversion to the Grignard with ethylmagnesium bromide, and subsequent Cu-catalyzed coupling with allyl bromide, see: Org. Synth. Coll., 6, 925 (1988).

For preparation of the cuprate and references for coupling with aryl halides to give diarylacetylenes, see: Org. Synth. Coll., 6, 916 (1988).

Dimetallation can be accomplished with a 2:1 molar mixture of n-BuLi and KO-t-Bu in THF, the second metallation occurring specifically at the ortho-position. Thus, the bis(TMS)-derivative can be prepared in excellent yield: J. Org. Chem., 55, 1311 (1990).

Weerachawanasak, P.; Praserthdam, P.; Panpranot, J. Liquid-Phase Hydrogenation of Phenylacetylene Over the Nano-Sized Pd/TiO2 Catalysts. J. Nanosci. Nanotechnol. 2014, 14 (4), 3170-3175.

Yoshida, H.; Zama, T.; Fujita, S. I.; Panpranot, J.; Arai, M. Liquid phase hydrogenation of phenylacetylene over Pd and PdZn catalysts in toluene: effects of alloying and CO2 pressurization. RSC Adv. 2014, 4 (47), 24922-24928.

GHS Hazard and Precautionary Statements

Hazard Statements: H304-H226-H319-H335

May be fatal if swallowed and enters airways. Flammable liquid and vapour. Causes serious eye irritation. May cause respiratory irritation.

Precautionary Statements: P261-P280f-P305+P351+P338-P301+P330+P331-P315

Avoid breathing dust/fume/gas/mist/vapours/spray. Wear protective clothing. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. IF SWALLOWED: Rinse mouth. Do NOT induce vomiting. Get immediate medical advice/attention.

Other References

Merck
14,3861
Beilstein
605461
Hazard Class
3
Packing Group
III
Harmonized Tariff Code
2902.90
TSCA
Yes
RTECS
DA0780000

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