Diphenylbutadiyne

Diphenylbutadiyne
Names
	IUPAC name 4-phenylbuta-1,3-diynylbenzene
	Other names diphenyldiacetylene
Identifiers
CAS Number	886-66-8 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:51588;
ChemSpider	63360;
ECHA InfoCard	100.011.776
EC Number	212-953-1;
PubChem CID	70174;
UNII	84WV7G15RN;
CompTox Dashboard (EPA)	DTXSID8061264 ;
	InChI InChI=1S/C16H10/c1-3-9-15(10-4-1)13-7-8-14-16-11-5-2-6-12-16/h1-6,9-12H Key: HMQFJYLWNWIYKQ-UHFFFAOYSA-N;
	SMILES C1=CC=C(C=C1)C#CC#CC2=CC=CC=C2;
Properties
Chemical formula	C16H10
Molar mass	202.256 g·mol−1
Appearance	white solid
Density	1.936 g/cm3
Melting point	86–87 °C (187–189 °F; 359–360 K)
Hazards
	GHS labelling:
Pictograms
Signal word	Warning
Hazard statements	H315, H319, H335
Precautionary statements	P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, P501
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Diphenylbutadiyne is the hydrocarbon with the formula (C₆H₅C₂)₂. It is a member of the diyne chemical class and can be made via the Glaser coupling of phenylacetylene^[2] However, a variety of other synthesis methods have been developed.^[3]^[4]

Diphenylbutadiyne forms a variety of metal-alkyne complexes. One example is the organonickel complex (C₅H₅Ni)₄C₄(C₆H₅)₂.^[5]

References

^ Surette, Jacqueline K. D.; MacDonald, Mary-Anne; Zaworotko, Michael J.; Singer, Robert D. (1994). "X-Ray Crystal Structure of 1,4-Diphenylbutadiyne". Journal of Chemical Crystallography. 24 (10): 715–717. doi:10.1007/BF01668237. S2CID 95454970.
^ Campbell, I. D.; Eglinton, G. (1965). "Diphenyldiacetylene". Organic Syntheses. 45: 39. doi:10.15227/orgsyn.045.0039.
^ Nishihara, Yasushi; Ikegashira, Kazutaka; Hirabayashi, Kazunori; Ando, Jun-Ichi; Mori, Atsunori; Hiyama, Tamejiro (2000). "Coupling Reactions of Alkynylsilanes Mediated by a Cu(I) Salt: Novel Syntheses of Conjugate Diynes and Disubstituted Ethynes". The Journal of Organic Chemistry. 65 (6): 1780–1787. doi:10.1021/jo991686k. PMID 10814151.
^ Batsanov, Andrei S.; Collings, Jonathan C.; Fairlamb, Ian J. S.; Holland, Jason P.; Howard, Judith A. K.; Lin, Zhenyang; Marder, Todd B.; Parsons, Alex C.; Ward, Richard M.; Zhu, Jun (2005). "Requirement for an Oxidant in Pd/Cu Co-Catalyzed Terminal Alkyne Homocoupling to Give Symmetrical 1,4-Disubstituted 1,3-Diynes". The Journal of Organic Chemistry. 70 (2): 703–706. doi:10.1021/jo048428u. PMID 15651824.
^ Mills, O. S.; Shaw, B. W. (1965). "Crystal Data for Some Dicyclopentadienyldinickel Alkyne Compounds". Acta Crystallographica. 18 (3): 562. doi:10.1107/S0365110X65001226.

[1] Surette, Jacqueline K. D.; MacDonald, Mary-Anne; Zaworotko, Michael J.; Singer, Robert D. (1994). "X-Ray Crystal Structure of 1,4-Diphenylbutadiyne". Journal of Chemical Crystallography. 24 (10): 715–717. doi:10.1007/BF01668237. S2CID 95454970.

[2] Campbell, I. D.; Eglinton, G. (1965). "Diphenyldiacetylene". Organic Syntheses. 45: 39. doi:10.15227/orgsyn.045.0039.

[3] Nishihara, Yasushi; Ikegashira, Kazutaka; Hirabayashi, Kazunori; Ando, Jun-Ichi; Mori, Atsunori; Hiyama, Tamejiro (2000). "Coupling Reactions of Alkynylsilanes Mediated by a Cu(I) Salt: Novel Syntheses of Conjugate Diynes and Disubstituted Ethynes". The Journal of Organic Chemistry. 65 (6): 1780–1787. doi:10.1021/jo991686k. PMID 10814151.

[4] Batsanov, Andrei S.; Collings, Jonathan C.; Fairlamb, Ian J. S.; Holland, Jason P.; Howard, Judith A. K.; Lin, Zhenyang; Marder, Todd B.; Parsons, Alex C.; Ward, Richard M.; Zhu, Jun (2005). "Requirement for an Oxidant in Pd/Cu Co-Catalyzed Terminal Alkyne Homocoupling to Give Symmetrical 1,4-Disubstituted 1,3-Diynes". The Journal of Organic Chemistry. 70 (2): 703–706. doi:10.1021/jo048428u. PMID 15651824.

[5] Mills, O. S.; Shaw, B. W. (1965). "Crystal Data for Some Dicyclopentadienyldinickel Alkyne Compounds". Acta Crystallographica. 18 (3): 562. doi:10.1107/S0365110X65001226.

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