Acridine
- Dibenzo [ b, e ] pyridine
- Benzo [b ] quinoline
- 9- Azaanthracen
- 2,3- benzoquinoline
- 10 - Azaanthracen
White to pale yellow solid
Fixed
1.1 g · cm -3 ( 20 ° C)
106-109 ° C ( sublimation from 100 ° C)
346 ° C
- Practically insoluble in water
- Soluble in diethyl ether, ethanol, benzene and carbon disulfide
Attention
2000 mg · kg -1 ( LD50, rat, oral)
Template: Infobox chemical / molecular formula search available
Acridine is a heterocyclic aromatic organic compound with the formula C13H9N. Acridine occurs in coal tar, forms colorless crystals and represents the chemical backbone of acridine
History
Acridine was the first time in 1870 by Carl Heinrich Caro and Graebe from coal tar isolated. The name is derived from the Latin word acer (hot) and is due to the biting skin irritating effect of acridine.
Production and representation
Acridine can be obtained from coal tar in the anthracene. From this it can be extracted by shaking with dilute sulfuric acid or sodium hydrogen sulfite as Natriumacridinsulfonat. The free base is liberated by reaction with sodium carbonate.
There is a number of synthetic processes are known which lead to acridine and its derivatives. August Bernthsen diphenylamine condensed with carboxylic acids in the presence of zinc chloride. This results in formic acid acridine, the higher homologues produce derivatives with the corresponding alkyl substituents.
Can be also obtained by acridine
- By conduction from the red-hot steam of N-phenyl -ortho- toluidine by a tube
- Condensation of diphenylamine with chloroform in the presence of aluminum chloride
- Directing steam through the ortho Aminophenylphenylmethan hot lead (II ) oxide
- Heat of salicylaldehyde with aniline and zinc chloride at 260 ° C
- Distillation of acridone over zinc dust.
- Dehalogenation of 9- Chloracridin
Properties
Physical Properties
Acridine crystallizes in colorless needles with a melting point of 106-110 ° C. Its salts in solution show blue fluorescence.
Chemical Properties
Acridine and its homologues are very stable compounds with weakly basic character. By oxidation with potassium permanganate produced Acridinsäure ( quinoline -2 ,3 -dicarboxylic acid) C9H5N (COOH ) 2
With alkyl and aryl halides acridine readily forms colored acridinium salts.
Use and derivatives
Acridine itself has virtually no industrial significance. The synthesis of acridine does not come from acridine.
Derivatives of acridine are, inter alia, the dyes acridine orange and acridine yellow, the drug ethacridine lactate and Acriflaviniumchlorid and acridinium esters that are of importance as luminophores.