1,2,3,4-tetraphenylnaphthalene

Structural formula
General
Surname	1,2,3,4-tetraphenylnaphthalene
Molecular formula	C 34 H 24
External identifiers / databases
EC number	623-131-0
ECHA InfoCard	100.151.838
PubChem	69783
Wikidata	Q1934549
properties
Molar mass	432.55 g mol −1
Physical state	firmly
Melting point	199-201 ° C
safety instructions
GHS labeling of hazardous substances Caution
H and P phrases	H: 315-319-335
	P: 261-305 + 351 + 338
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

1,2,3,4-Tetraphenylnaphthalene is a chemical compound from the group of polycyclic aromatic hydrocarbons .

Extraction and presentation

1,2,3,4-Tetraphenylnaphthalene can be obtained by reacting tetraphenylcyclopentadienone , anthranilic acid and 1,2-dimethoxyethane .

properties

1,2,3,4-tetraphenylnaphthalene is an interesting example of polymorphism . The melting point of the compound after crystallization from solution is lower than the melting point of the compound after it has been melted and cooled again.

use

The triplet excited state of 1,2,3,4-tetraphenylnaphthalenes is a primary intermediate of the photochemical conversion of 7,7'-dimethylgerma-1,4,5,6-tetraphenyl-2,3-benzonorbornadiene (GNB) in hexane solutions. The compound is often used in chemistry classes as an example of Diels-Alder reactions .

Individual evidence

↑ ^a ^b ^c ^d ^e data sheet 1,2,3,4-tetraphenylnaphthalene, 97% from Sigma-Aldrich , accessed on June 10, 2014 ( PDF ).
↑ Pavia, DL; Lampman, GM; Kriz, GS Organic Laboratory Techniques, BENZYNE FORMATION AND A DIELS-ALDER REACTION ; Saunders: New York, NY, 1995; pp 286-289, 293-296, 429-434
↑ Louis F. Fieser, Makhluf J. Haddadin: 1,2,3,4-Tetraphenylnaphthalene In: Organic Syntheses . 46, 1966, p. 107, doi : 10.15227 / orgsyn.046.0107 ; Coll. Vol. 5, 1973, p. 1037 ( PDF ).
↑ ^a ^b W. H. Ojala, HL Gustafson, CR Ojala: A polymorph of 1,2,3,4-tetraphenylnaphthalene. In: Acta Crystallographica Section C Crystal Structure Communications. 50, pp. 1602-1604, doi : 10.1107 / S010827019301371X .

[Sigma-1] ↑ ^a ^b ^c ^d ^e data sheet 1,2,3,4-tetraphenylnaphthalene, 97% from Sigma-Aldrich , accessed on June 10, 2014 ( PDF ).

[2] Pavia, DL; Lampman, GM; Kriz, GS Organic Laboratory Techniques, BENZYNE FORMATION AND A DIELS-ALDER REACTION ; Saunders: New York, NY, 1995; pp 286-289, 293-296, 429-434

[3] Louis F. Fieser, Makhluf J. Haddadin: 1,2,3,4-Tetraphenylnaphthalene In: Organic Syntheses . 46, 1966, p. 107, doi : 10.15227 / orgsyn.046.0107 ; Coll. Vol. 5, 1973, p. 1037 ( PDF ).

[DOI10.1107/S010827019301371X-4] W. H. Ojala, HL Gustafson, CR Ojala: A polymorph of 1,2,3,4-tetraphenylnaphthalene. In: Acta Crystallographica Section C Crystal Structure Communications. 50, pp. 1602-1604, doi : 10.1107 / S010827019301371X .