1,3,5-triphenylbenzene

Structural formula
General
Surname	1,3,5-triphenylbenzene
Molecular formula	C 24 H 18
Brief description	light brown solid
External identifiers / databases
EC number	210-318-3
ECHA InfoCard	100.009.382
PubChem	11930
ChemSpider	11436
Wikidata	Q27258308
properties
Molar mass	306.40 g mol −1
Physical state	firmly
density	1.199 g cm −3
Melting point	172-174 ° C
boiling point	460 ° C
solubility	practically insoluble in water; soluble in ethanol and ether ; very soluble in benzene ;
safety instructions
GHS labeling of hazardous substances	no GHS pictograms
	no GHS pictograms
H and P phrases	H: no H-phrases
	P: no P-phrases
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

1,3,5-Triphenylbenzene is a chemical compound from the group of benzene derivatives .

Extraction and presentation

1,3,5-Triphenylbenzene can be obtained by condensation of acetophenone using acids or by cyclopolymerization from phenylacetylene .

In the presence of traces of sodium methoxide, β-nitrostyrenes and two equivalents of dimethylformamide dimethylacetal in DMF form 1,3,5-triphenylbenzene in moderate yields (up to 40%).

properties

1,3,5-triphenylbenzene is a light brown solid that is practically insoluble in water. It has an orthorhombic crystal structure with the space group Pna 2 ₁ (space group no. 33) . Template: room group / 33

use

1,3,5-triphenylbenzene can be used to make other chemical compounds.

Individual evidence

↑ ^a ^b data sheet 1,3,5-triphenylbenzene, 99 +% from AlfaAesar, accessed on February 22, 2018 ( PDF )(JavaScript required) .
↑ ^a ^b ^c ^d ^e data sheet 1,3,5-triphenylbenzene, 97% from Sigma-Aldrich , accessed on February 21, 2018 ( PDF ).
↑ ^a ^b ^c ^d ^e William M. Haynes: CRC Handbook of Chemistry and Physics, 97th Edition . CRC Press, 2016, ISBN 978-1-4987-5429-3 , pp. 458 ( limited preview in Google Book search).
↑ Google Patents: DE1085864B - Process for the production of 1, 3, 5-triphenylbenzene by condensation of acetophenone using acids - Google Patents , accessed on February 22, 2018
^ Paul N. Rylander: Organic Syntheses with Noble Metal Catalysts . Elsevier, 2012, ISBN 978-0-323-16261-6 , pp. 330 ( limited preview in Google Book search).
↑ George Butler: Cyclopolymerization and Cyclocopolymerization . CRC Press, 1992, ISBN 978-0-8247-8625-0 , pp. 192 ( limited preview in Google Book search).
↑ TY Kim, HS Kim, KY Lee, JN Kim: N, N -dimethylformamide dimethylacetal (DMF-DMA) catalyzed formation of 1,3,5-trisubstituted benzene derivatives from α, β- unsaturated nitro compounds . In: Bull. Korean Chem. Soc. tape 20 , no. 11 , 1999, p. 1255–1256 ( PDF ( memento of October 26, 2017 in the Internet Archive )).
↑ MS Farag: The crystal structure of 1,3,5-triphenylbenzene. In: Acta Crystallographica . 7, 1954, pp. 117-121, doi: 10.1107 / S0365110X54000242 .
^ HO Wirth, W. Kern, E. Schmitz: Synthesis and properties of branched oligophenylenes, which are derived from 1,3,5-triphenylbenzene. 14th communication. In: The Macromolecular Chemistry . 68, pp. 69-99, doi: 10.1002 / macp.1963.020680106 .

[Alfa-1] ta sheet 1,3,5-triphenylbenzene, 99 +% from AlfaAesar, accessed on February 22, 2018 ( PDF )(JavaScript required) .

[Sigma-2] ↑ ^a ^b ^c ^d ^e data sheet 1,3,5-triphenylbenzene, 97% from Sigma-Aldrich , accessed on February 21, 2018 ( PDF ).

[William_M._Haynes-3] William M. Haynes: CRC Handbook of Chemistry and Physics, 97th Edition . CRC Press, 2016, ISBN 978-1-4987-5429-3 , pp. 458 ( limited preview in Google Book search).

[google.com-4] Google Patents: DE1085864B - Process for the production of 1, 3, 5-triphenylbenzene by condensation of acetophenone using acids - Google Patents , accessed on February 22, 2018

[Paul_N._Rylander-5] Paul N. Rylander: Organic Syntheses with Noble Metal Catalysts . Elsevier, 2012, ISBN 978-0-323-16261-6 , pp. 330 ( limited preview in Google Book search).

[George_Butler-6] George Butler: Cyclopolymerization and Cyclocopolymerization . CRC Press, 1992, ISBN 978-0-8247-8625-0 , pp. 192 ( limited preview in Google Book search).

[7] TY Kim, HS Kim, KY Lee, JN Kim: N, N -dimethylformamide dimethylacetal (DMF-DMA) catalyzed formation of 1,3,5-trisubstituted benzene derivatives from α, β- unsaturated nitro compounds . In: Bull. Korean Chem. Soc. tape 20 , no. 11 , 1999, p. 1255–1256 ( PDF ( memento of October 26, 2017 in the Internet Archive )).

[DOI10.1107/S0365110X54000242-8] MS Farag: The crystal structure of 1,3,5-triphenylbenzene. In: Acta Crystallographica . 7, 1954, pp. 117-121, doi: 10.1107 / S0365110X54000242 .

[DOI10.1002/macp.1963.020680106-9] HO Wirth, W. Kern, E. Schmitz: Synthesis and properties of branched oligophenylenes, which are derived from 1,3,5-triphenylbenzene. 14th communication. In: The Macromolecular Chemistry . 68, pp. 69-99, doi: 10.1002 / macp.1963.020680106 .