Triphenylene

from Wikipedia, the free encyclopedia
Structural formula
Structural formula of triphenylene
General
Surname Triphenylene
other names

9,10-benzophenanthrene

Molecular formula C 18 H 12
Brief description

white to light yellow solid

External identifiers / databases
CAS number 217-59-4
EC number 205-922-9
ECHA InfoCard 100.005.385
PubChem 9170
Wikidata Q2975866
properties
Molar mass 228.29 g mol −1
Physical state

firmly

density

1.12 g cm −3

Melting point

195-198 ° C

boiling point

438 ° C

solubility
  • almost insoluble in water
  • soluble in ethanol
  • easily soluble in benzene and chloroform
safety instructions
GHS labeling of hazardous substances
05 - Corrosive 09 - Dangerous for the environment

danger

H and P phrases H: 318-410
P: 280-305 + 351 + 338-310
As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Triphenylene is a chemical compound from the group of polycyclic aromatic hydrocarbons and consists of four linked rings.

Occurrence

Triphenylene occurs naturally in coal tar and fossil fuels.

Extraction and presentation

Triphenylene can be obtained by a modified Haworth reaction starting from succinic anhydride with 9-phenanthrylmagnesium bromide and subsequent cyclization with hydrogen fluoride . Other synthetic methods are also known. The most common synthesis starts from cyclohexanone .

properties

Triphenylene is a white to light yellow solid that is insoluble in water. It has an orthorhombic crystal structure with the space group P 2 1 2 1 2 1 (space group no. 19) . Template: room group / 19

use

Triphenylene derivatives are used as liquid crystals.

Individual evidence

  1. a b c d e data sheet triphenylene, 98% from Sigma-Aldrich , accessed on October 18, 2015 ( PDF ).
  2. ^ Carl L. Yaws: Thermophysical Properties of Chemicals and Hydrocarbons . William Andrew, 2014, ISBN 978-0-323-29060-9 , pp. 335 ( limited preview in Google Book search).
  3. a b c d William M. Haynes: CRC Handbook of Chemistry and Physics, 96th Edition . CRC Press, 2015, ISBN 978-1-4822-6097-7 , pp. 540 ( limited preview in Google Book search).
  4. a b Entry on triphenylene in the GESTIS substance database of the IFA , accessed on January 8, 2020(JavaScript required) .
  5. ^ A b Ronald G. Harvey: Polycyclic Aromatic Hydrocarbons Chemistry and Carcinogenicity . CUP Archive, 1991, ISBN 978-0-521-36458-4 , pp. 157 ( limited preview in Google Book search).
  6. Eric Clar: Polycyclic Hydrocarbons . Springer Science & Business Media, 2013, ISBN 978-3-662-01665-7 , pp. 241 ( limited preview in Google Book search).
  7. FR Ahmed, J. Trotter: The crystal structure of triphenylene. In: Acta Crystallographica. 16, 1963, p. 503, doi : 10.1107 / S0365110X63001365 .
  8. ^ Glenn H. Brown: Advances in Liquid Crystals . Academic Press, 2013, ISBN 978-1-4831-9137-9 , pp. 47 ( limited preview in Google Book search).