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501-65-5 - Diphenylacetylene, 99% - Tolan - A13979 - Alfa Aesar

A13979 Diphenylacetylene, 99%

CAS Number
501-65-5
Synonyms
Tolan

Size Price ($) Quantity Availability
5g 18.99
25g 48.31
100g 147.60
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Diphenylacetylene, 99%

MDL
MFCD00004786
EINECS
207-926-6

Chemical Properties

Formula
C14H10
Formula Weight
178.23
Melting point
58-62°
Boiling Point
170°/19mm
Density
0.990
Solubility
Miscible with ether and hot alcohol. Immiscible with water.

Applications

Diphenylacetylene is often used as a building block in organic and organometallic chemistry. It acts as dienophile and under goes Diels-Alder reaction with tetraphenylcyclopentadienone to prepare hexaphenylbenzene. It acts as a precursor in the preparation of 3-alkoxycyclopropene by reacting with benzal chloride in the presence of potassium t-butoxide.

Notes

Incompatible with strong oxidizing agents.

Literature References

For an example of use as a Diels-Alder dienophile, see: Org. Synth. Coll., 5, 604 (1973).

For transfer of methylene groups from dimsyl sodium, giving 2,3-diphenylbutadiene, see: Org. Synth. Coll., 6, 531 (1988).

Can be oxidized to benzil using iodine-DMSO: Synthesis, 131 (1991).

Shi, Y.; Li, G.; Zhao, B.; Chen, Y.; Chao, P.; Zhang, H.; Wang, X.; Wang, T. Synthesis and optical properties of cationic cyclopentadienyl iron complexes with diphenylacetylene chromophores. Inorg. Chim. Acta 2015, 427, 259-265.

Le, K. V.; Aya, S.; Ogino, S.; Okano, K.; Araoka, F.; Takezoe, H. Large Twist Elastic Constant in Diphenylacetylene-Core-Based Liquid Crystals. Mol Cryst Liq Cryst 2015, 614 (1), 124-127.

Other References

Merck
14,9504
Beilstein
606478
Harmonized Tariff Code
2902.90
TSCA
Yes

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