Diphenylacetylene

Diphenylacetylene: Diphenylacetylene

IUPAC name

2-phenylethynylbenzene

Other names

Tolan
Diphenylacetylene
1,2-diphenylethyne

Identifiers

CAS number 501-65-5^Y

PubChem 10390

ChemSpider 9961^Y

ChEBI CHEBI:51579^Y

ChEMBL CHEMBL223309^Y

Jmol-3D images Image 1

SMILES

c1ccc(cc1)C#Cc2ccccc2

InChI

InChI=1S/C14H10/c1-3-7-13(8-4-1)11-12-14-9-5-2-6-10-14/h1-10H^Y
Key: JRXXLCKWQFKACW-UHFFFAOYSA-N^Y
InChI=1/C14H10/c1-3-7-13(8-4-1)11-12-14-9-5-2-6-10-14/h1-10H
Key: JRXXLCKWQFKACW-UHFFFAOYAN

Properties

Molecular formula C₁₄H₁₀

Molar mass 178.24 g/mol

Appearance colorless solid

Density 0.990 g cm^-3, solid

Melting point
62.5 °C, 335.7 K, 144.5 °F

Boiling point
0–97 °C/0.3 mmHg

Solubility in water insoluble

Structure

Molecular shape sp2 and sp at carbon

Dipole moment 0 D

Hazards

MSDS Oxford MSDS

Related compounds

Related compounds C₂Me₂
Dimethylacetylenedicarboxylate

Y (verify) (what is: Y/N?)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)

Infobox references

Diphenylacetylene is the chemical compound C₆H₅C≡CC₆H₅. The molecule consists of phenyl groups attached to both ends of an alkyne. It is a colorless crystalline material that is widely used as a building block in organic and as a ligand in organometallic chemistry.

Preparation

Several preparations for this compound exist:

benzil is condensed with hydrazine to give the bis(hydrazone), which is oxidized with mercury oxide.^[1]

stilbene is brominated, then dehydrohalogenated,^[2] but the product can be contaminated with stilbene, which is difficult to remove.^[1]

One method starts from iodobenzene and the copper salt of phenylacetylene in the Castro-Stephens coupling

Interesting derivatives

Reaction of Ph₂C₂ with tetraphenylcyclopentadienone results in the formation of hexaphenylbenzene.^[3]

Reaction of Ph₂C₂ with benzal chloride in the presence of potassium t-butoxide affords the 3-alkoxycyclopropene which coverts to the cyclopropenium ion.^[4]

References

^ ^a ^b Cope, A. C.; Smith, D. S.; Cotter, R. J., "Diphenylacetylene", Org. Synth., http://www.orgsyn.org/orgsyn/orgsyn/prepContent.asp?prep=cv4p0377 ; Coll. Vol. 4: 377

^ Lee Irvin Smith and M. M. Falkof, "Diphenylacetylene", Org. Synth., http://www.orgsyn.org/orgsyn/orgsyn/prepContent.asp?prep=cv3p0350 ; Coll. Vol. 3: 350

^ Fieser, L. F., "Hexaphenylbenzene", Org. Synth., http://www.orgsyn.org/orgsyn/orgsyn/prepContent.asp?prep=cv5p0604 ; Coll. Vol. 5: 604

^ Xu, R. Breslow, R., "1,2,3-Triphenylcyclopropendium Bromide", Org. Synth., http://www.orgsyn.org/orgsyn/orgsyn/prepContent.asp?prep=cv9p0730 ; Coll. Vol. 9: 730

Categories:
Alkynes
Hydrocarbons

Diphenylacetylene



IUPAC name 2-phenylethynylbenzene
Other names Tolan Diphenylacetylene 1,2-diphenylethyne
Identifiers
CAS number	501-65-5^Y
PubChem	10390
ChemSpider	9961^Y
ChEBI	CHEBI:51579^Y
ChEMBL	CHEMBL223309^Y
Jmol-3D images	Image 1
SMILES c1ccc(cc1)C#Cc2ccccc2
InChI InChI=1S/C14H10/c1-3-7-13(8-4-1)11-12-14-9-5-2-6-10-14/h1-10H^Y Key: JRXXLCKWQFKACW-UHFFFAOYSA-N^Y InChI=1/C14H10/c1-3-7-13(8-4-1)11-12-14-9-5-2-6-10-14/h1-10H Key: JRXXLCKWQFKACW-UHFFFAOYAN
Properties
Molecular formula	C₁₄H₁₀
Molar mass	178.24 g/mol
Appearance	colorless solid
Density	0.990 g cm^-3, solid
Melting point	62.5 °C, 335.7 K, 144.5 °F
Boiling point	0–97 °C/0.3 mmHg
Solubility in water	insoluble
Structure
Molecular shape	sp2 and sp at carbon
Dipole moment	0 D
Hazards
MSDS	Oxford MSDS
Related compounds
Related compounds	C₂Me₂ Dimethylacetylenedicarboxylate
Y (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

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Look at other dictionaries:

diphenylacetylene — /duy fen l euh set l een , feen /, n. Chem. tolan. [DIPHENYL + ACETYLENE] * * * … Universalium
diphenylacetylene — noun A colourless crystalline material widely used as a building block in organic chemistry and as a ligand in organometallic chemistry … Wiktionary
diphenylacetylene — /duy fen l euh set l een , feen /, n. Chem. tolan. [DIPHENYL + ACETYLENE] … Useful english dictionary
Difenilacetileno — Difenilacetileno … Wikipedia Español
Dithiolene — A 1,2 dithiolene is an unsaturated bidentate ligand wherein the two donor atoms are sulfur. These ligands readily form complexes by co ordinating to metal centres via the sulfur atoms; such complexes are often referred to as metallodithiolenes or … Wikipedia
Carbometalation — is an organometallic reaction involving the nucleophilic addition to alkenes and alkynes of a diverse range of organometallic reagents such as organolithium compounds, organocopper compounds and Grignard reagents according to the following… … Wikipedia
Organonickel — chemistry is a branch of organometallic chemistry that deals with organic compounds feature nickel carbon bonds.[1][2] They are used as a catalyst, as a building block in organic chemistry and in chemical vapor deposition. Organonickel compounds… … Wikipedia
Metal dithiolene complex — Metal dithiolene complexes are complexes containing dithiolene ligands. Dithiolene ligands are unsaturated bidentate ligand wherein the two donor atoms are sulfur. Dithiolenes are often referred to as metallodithiolenes or dithiolene complexes… … Wikipedia
Tolan — may refer to:* Tollan, Mesoamerican city * Diphenylacetylene … Wikipedia
Organopalladium — chemistry is a branch of organometallic chemistry that deals with organic palladium compounds and their reactions. Palladium is often used as a catalyst in the reduction of alkenes and alkynes with hydrogen. This process involves the formation of … Wikipedia

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Diphenylacetylene

Preparation

Interesting derivatives

References

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Diphenylacetylene

Preparation

Interesting derivatives

References

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