“Diphenylacetylene”的意思、由来-开放百科全书

词条

Diphenylacetylene

释义

Preparation
Derivatives
References

{{chembox
| Watchedfields = changed
| verifiedrevid = 443695347
| Name = Diphenylacetylene
| ImageFile = DiphenylacetyleneSVG.svg
| ImageSize = 200
| ImageName =
| ImageFile1 = Diphenylacetylene-3D-balls.png
| ImageSize1 = 200
| ImageFile2 = Diphenylacetylene-3D-vdW.png
| ImageSize2 = 200
| PIN = 1,1'-(Ethyne-1,2-diyl)dibenzene
| OtherNames = 1,2-Diphenylethyne
2-Phenylethynylbenzene
Tolan
Diphenylacetylene
|Section1={{Chembox Identifiers
| ChEBI_Ref = {{ebicite|correct|EBI}}
| ChEBI = 51579
| SMILES = c1ccc(cc1)C#Cc2ccccc2
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 9961
| ChEMBL_Ref = {{ebicite|correct|EBI}}
| ChEMBL = 223309
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/C14H10/c1-3-7-13(8-4-1)11-12-14-9-5-2-6-10-14/h1-10H
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = JRXXLCKWQFKACW-UHFFFAOYSA-N
| CASNo_Ref = {{cascite|correct|CAS}}
| CASNo = 501-65-5
| PubChem = 10390
| InChI = 1/C14H10/c1-3-7-13(8-4-1)11-12-14-9-5-2-6-10-14/h1-10H
| InChIKey = JRXXLCKWQFKACW-UHFFFAOYAN
}}
|Section2={{Chembox Properties
| C=14|H=10
| Appearance = Colorless solid
| Density = 0.990 g cm⁻³
| Solubility = Insoluble
| MeltingPtC = 62.5
| MeltingPt_notes =
| BoilingPtC = 170
| BoilingPt_notes = at 19 mmHg
|Section3={{Chembox Structure
| MolShape =
| Dipole = 0 D
|Section7={{Chembox Hazards
| ExternalSDS = Oxford MSDS
|Section8={{Chembox Related
| OtherCompounds = 2-Butyne
Dimethyl acetylenedicarboxylate
}}

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 synthesis and as a ligand in organometallic chemistry.

Preparation

In one preparation for this compound, benzil is condensed with hydrazine to give the bis(hydrazone), which is oxidized with mercury oxide.^[1] Alternatively stilbene is brominated, and the resulting dibromodiphenylethane is subjected to dehydrohalogenated,^[2] Yet another method starts involves the coupling iodobenzene and the copper salt of phenylacetylene in the Castro-Stephens coupling.

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

1. ^{{OrgSynth |author1=Cope, A. C.|author2=Smith, D. S.|author3=Cotter, R. J. | title = Diphenylacetylene | collvol = 4 | collvolpages = 377 | prep = cv4p0377}}
2. ^{{OrgSynth | author = Lee Irvin Smith and M. M. Falkof | collvol = 3 | collvolpages = 350 | prep = cv3p0350 | title = Diphenylacetylene}}
3. ^{{OrgSynth | author = Fieser, L. F. | title = Hexaphenylbenzene | collvol = 5 | collvolpages = 604 | prep = cv5p0604}}
4. ^{{OrgSynth|first1 = Ruo|last1 = Xu|first2 = Ronald|last2 = Breslow|authorlink2 = Ronald Breslow|title = 1,2,3-Triphenylcyclopropendium Bromide|volume = 74|pages = 72|doi = 10.15227/orgsyn.074.0072|year = 1997|prep = CV9P0730|collvol = 9|collvolpages = 730}}

3 : Alkynes|Hydrocarbons|Phenyl compounds

随便看

开放百科全书收录14589846条英语、德语、日语等多语种百科知识，基本涵盖了大多数领域的百科知识，是一部内容自由、开放的电子版国际百科全书。