Biphenylene

Structural formula
General
Surname	Biphenylene
other names	Diphenylene
Molecular formula	C 12 H 8
Brief description	yellowish solid
External identifiers / databases
EC number	690-155-6
ECHA InfoCard	100.217.287
PubChem	9214
Wikidata	Q3560509
properties
Molar mass	152.19 g mol −1
Physical state	firmly
density	0.975 g cm −3 (18 ° C)
Melting point	113-114 ° C
safety instructions
GHS hazard labeling ; no classification available
GHS hazard labeling ; no classification available
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Biphenylene is a chemical compound from the group of polycyclic aromatic hydrocarbons .

Extraction and presentation

Biphenyls, by dimerization of dehydrobenzene be won. It can also be produced by reductive dehalogenation of o - bromofluorobenzene with lithium amalgam . The compound was first synthesized in 1941 by Warren C. Lothrop . Other chemists had previously published the first synthesis, but none of them could be confirmed.

properties

Biphenylene is a solid that is in the form of pale yellowish prismatic crystals. The boiling point is 260 ° C, but below this temperature it sublimes at normal pressure. Its odor is typical of aromatic hydrocarbons and is reminiscent of xylene . The compound is stable at room temperature and can be stored for years. In spite of its structure, ring opening of the compound occurs only in a few reactions ( e.g. catalytic hydrogenation ). The molecule is planar and has an almost right-angled CC angle in the four-membered ring, but a distortion in the six-membered ring that leads to angles between 115.2 ° and 122.6 °.

Individual evidence

↑ ^a ^b ^c Fritz Vögtle : Charming molecules of organic chemistry . Springer-Verlag, 1989, ISBN 978-3-322-96705-3 , pp. 133 ( limited preview in Google Book search).
↑ ^a ^b Data sheet biphenylene, 99% from Sigma-Aldrich , accessed on September 27, 2015 ( PDF ).
^ Carl L. Yaws: Thermophysical Properties of Chemicals and Hydrocarbons . William Andrew, 2014, ISBN 978-0-323-29060-9 , pp. 596 ( limited preview in Google Book search).
↑ This substance has either not yet been classified with regard to its hazardousness or a reliable and citable source has not yet been found.
^ Warren C. Lothrop: Biphenylenes. In: Journal of the American Chemical Society. 63, 1941, p. 1187, doi : 10.1021 / ja01850a007 .
↑ MP Cava: Cyclobutadiene and Related Compounds . Elsevier, 1967, ISBN 978-0-323-16312-5 , pp. 256 ( limited preview in Google Book Search).

[Fritz_Vögtle-1] Fritz Vögtle : Charming molecules of organic chemistry . Springer-Verlag, 1989, ISBN 978-3-322-96705-3 , pp. 133 ( limited preview in Google Book search).

[Sigma-2] Data sheet biphenylene, 99% from Sigma-Aldrich , accessed on September 27, 2015 ( PDF ).

[Carl_L._Yaws-3] Carl L. Yaws: Thermophysical Properties of Chemicals and Hydrocarbons . William Andrew, 2014, ISBN 978-0-323-29060-9 , pp. 596 ( limited preview in Google Book search).

[NV-4] This substance has either not yet been classified with regard to its hazardousness or a reliable and citable source has not yet been found.

[DOI10.1021/ja01850a007-5] Warren C. Lothrop: Biphenylenes. In: Journal of the American Chemical Society. 63, 1941, p. 1187, doi : 10.1021 / ja01850a007 .

[M.P._Cava-6] MP Cava: Cyclobutadiene and Related Compounds . Elsevier, 1967, ISBN 978-0-323-16312-5 , pp. 256 ( limited preview in Google Book Search).