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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