Diphenylacetylene

Synonym(s):Tolan

CAS NO.：501-65-5
Empirical Formula: C14H10
Molecular Weight: 178.23
MDL number: MFCD00004786
EINECS: 207-926-6
SAFETY DATA SHEET (SDS)
Update Date: 2023-05-04 15:12:50

What is Diphenylacetylene?

Chemical properties

white crystals

The Uses of Diphenylacetylene

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.

The Uses of Diphenylacetylene

Organic synthesis, purified grade, primary fluor or wavelength shifter in soluble scintillators.

Definition

ChEBI: An arylacetylene that is acetylene in which the hydrogens are replaced by phenyl groups.

Synthesis Reference(s)

Canadian Journal of Chemistry, 61, p. 86, 1983 DOI: 10.1139/v83-015
Journal of the American Chemical Society, 87, p. 863, 1965 DOI: 10.1021/ja01082a029
The Journal of Organic Chemistry, 51, p. 3830, 1986 DOI: 10.1021/jo00370a016

Purification Methods

Crystallise tolan from EtOH. [Beilstein 5 H 656, 5 IV 2276.]

Properties of Diphenylacetylene

Melting point:	59-61 °C (lit.)
Boiling point:	170 °C/19 mmHg (lit.)
Density	0.99 g/mL at 25 °C (lit.)
refractive index	1.6415 (estimate)
Flash point:	170°C/19mm
storage temp.	Sealed in dry,2-8°C
form	Crystalline Powder and Chunks
Specific Gravity	0.99
color	Light yellow to brownish
Water Solubility	Miscible with ether and hot alcohol. Immiscible with water.
Merck	14,9504
BRN	606478
Stability:	Stable. Combustible. Incompatible with strong oxidizing agents.
CAS DataBase Reference	501-65-5(CAS DataBase Reference)
NIST Chemistry Reference	Diphenylethyne(501-65-5)
EPA Substance Registry System	Benzene, 1,1'-(1,2-ethynediyl)bis- (501-65-5)