Acridine

Structural formula
General
Surname	Acridine
other names	Dibenzo [ b, e ] pyridine; Benzo [ b ] quinoline; 9-azaanthracene; 2,3-benzoquinoline; 10-azaanthracene;
Molecular formula	C 13 H 9 N
Brief description	white to pale yellow solid
External identifiers / databases
EC number	205-971-6
ECHA InfoCard	100.005.429
PubChem	9215
Wikidata	Q342713
properties
Molar mass	179.22 g mol −1
Physical state	firmly
density	1.1 g cm −3 (20 ° C)
Melting point	106–109 ° C (sublimation from 100 ° C)
boiling point	346 ° C
solubility	practically insoluble in water; soluble in diethyl ether , ethanol , benzene and carbon disulfide ;
safety instructions
H and P phrases	H: 302-315-319-335-410
	P: 273-302 + 352-304 + 340-305 + 351 + 338
Toxicological data	2000 mg kg −1 ( LD 50 , rat , oral )
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Acridine is a heteroaromatic organic compound with the empirical formula C ₁₃ H ₉ N. Acridine occurs in coal tar , forms colorless crystals and is the basic chemical structure of acridine dyes .

history

Acridine was first isolated from coal tar by Carl Graebe and Heinrich Caro in 1870 . The name is derived from the Latin acer (sharp) and is due to the acridine's irritating effects on the skin.

Extraction and presentation

Acridine can be obtained from coal tar in the anthracene fraction. From this it can be extracted as sodium acridine sulfonate by shaking it out with dilute sulfuric acid or sodium hydrogen sulfite . The free base is released by reaction with sodium carbonate .

A number of synthesis processes are known which lead to acridine and its derivatives . August Bernthsen condensed diphenylamine with carboxylic acids in the presence of zinc chloride . Formic acid produces acridine, the higher homologues produce derivatives with the corresponding alkyl substituents .

Acridine can also be obtained through

Passing steam of the N -phenyl- ortho- toluidine through a red-hot pipe
Condensation of diphenylamine with chloroform in the presence of aluminum chloride
Conduction of steam of the ortho- aminophenylphenylmethane over hot lead (II) oxide
Heating salicylaldehyde with aniline and zinc chloride to 260 ° C
Distillation of acridon over zinc dust .
Reductive dehalogenation of 9-chloroacridine

properties

Physical Properties

Acridine crystallizes in colorless needles with a melting point of 106–110 ° C. Its salts show blue fluorescence in solution .

Chemical properties

Acridine and its homologues are very stable compounds with a weakly basic character. By oxidation with potassium permanganate produced acridine acid (quinoline-2,3-dicarboxylic acid) C ₉ H ₅ N (COOH) ₂ .

Acridine forms slightly colored acridinium salts with alkyl and aryl halides .

Uses and derivatives

Acridine itself has practically no industrial importance. The synthesis of acridine dyes does not start from acridine.

Acridine derivatives include the dyes acridine orange and acridine yellow , the drugs acriflavinium chloride , amsacrine and ethacridine lactate, and the acridinium esters , which are important as luminophores .

Individual evidence

↑ ^a ^b ^c ^d ^e ^f Entry on acridine. In: Römpp Online . Georg Thieme Verlag, accessed on December 28, 2014.
↑ ^a ^b ^c ^d ^e ^f ^g Data sheet acridine (PDF) from Merck , accessed on March 20, 2011.
↑ ^a ^b ^c ^d G. Collin, H. Höke: Acridine , in: Ullmann's Encyclopedia of Industrial Chemistry , 2005 , Wiley-VCH Weinheim.
↑ Carl Graebe, Heinrich Caro: About acridine . In: Reports of the German Chemical Society . tape 3 , no. 2 , July 1870, p. 746-747 , doi : 10.1002 / cber.18700030223 .
^ A. Bernthsen : Acridine , in: Liebigs Ann. 1884 , 224 , 1-56; doi : 10.1002 / jlac.18842240102 .
↑ C. Graebe : About pyrogenic formation of acridine , in: Chem. Ber. 1884 , 17 , 1370-1371; doi : 10.1002 / cber.188401701353 .
↑ O. Fischer , G. Körner: New Formation of Acridine , in: Chem. Ber. 1884 , 17 , 101-102; doi : 10.1002 / cber.18840170122 .
↑ O. Fischer , H. Schütte: About some syntheses of the acridine series and about 2,7-phenylamidonaphtol , in: Chem. Ber. 1893 , 26 , 3085-3089; doi : 10.1002 / cber.189302603150 .
↑ R. Möhlau : Formation of Acridine , in: Chem. Ber. 1886 , 19 , 2451-2453; doi : 10.1002 / cber.188601902180 .
↑ C. Graebe , K. Lagodzinski: About phenylantranilic acid and acridone , in Chem. Ber. 1892 , 25 , 1733-1736; doi : 10.1002 / cber.189202501276 .
↑ C. Graebe , H. Caro : Ueber Acridin , in: Chem. Ber 1880 , 13 , 99-103; doi : 10.1002 / cber.18800130128 .