Acridine

Title: Acridine
CAS Registry Number: 260-94-6
Additional Names: Dibenzo[b,e]pyridine; 10-azaanthracene
Molecular Formula: C13H9N
Molecular Weight: 179.22
Percent Composition: C 87.12%, H 5.06%, N 7.82%
Literature References: Occurs in coal tar. Isoln: Graebe, Caro, Ann. 158, 265 (1871); from high boiling tar oils: Wirth, DE 440771 (1926). Prepn from N-phenylanthranilic acid: Perkin, Clemo, GB 214756 (1923); from Ca-anthranilate: Koller, Krakauer, Monatsh. Chem. 50, 51 (1928); by passing benzylaniline vapor over red-hot platinum wire: Meyer, Hofmann, ibid. 37, 698 (1916); cf. Ullmann, Ber. 40, 2521 (1907). Absorption spectrum: Pinnow, J. Prakt. Chem. [2] 66, 276 (1902). Toxicity: S. D. Rubbo, Br. J. Exp. Pathol. 28, 1 (1947). Reviews: A. Albert, The Acridines (St. Martin's Press, New York, 2nd ed., 1966); R. M. Acheson, Acridines (Interscience, New York, 2nd ed., 1973).
Properties: Pale yellow orthorhombic plates, needles from diluted alcohol. There are five crystalline forms of acridine all of which melt below 111°. Purified acridine mp 110-111°; commercial samples mp 107° or mp 109°. Begins to sublime at 100°. bp760 346°; also reported as bp760 >360°. Volatile with steam. Slightly sol in boiling water, liquid ammonia, liquid sulphur dioxide; sparingly sol in light petroleum; freely sol in alcohol, ether, hydrocarbons, carbon disulfide. 1 gm sol in <1 ml boiling benzene or alcohol; 5 ml benzene (20°); 6 ml alcohol (20°); 16 ml of ether (20°); 1.8 ml boiling cyclohexane. d 1.27-1.28. Dilute solns of acridine and its salts have a violet and green fluorescence, respectively. Weak base, colors litmus paper blue, forms yellow crystalline salts with mineral acids. Forms colored quaternary ammonium compounds (acridinium compounds), by the action of alkyl and aryl halides and sulfates. LD50 s.c. in mice: 0.40 g/kg (Rubbo).
Melting point: mp 110-111°; mp 107° or mp 109°
Boiling point: bp760 346°; bp760 >360°
Density: d 1.27-1.28
Toxicity data: LD50 s.c. in mice: 0.40 g/kg (Rubbo)
CAUTION: Strongly irritating to skin, mucous membranes. See: Clinical Toxicology of Commercial Products, R. E. Gosselin et al., Eds. (Williams & Wilkins, Baltimore, 5th ed., 1984) Section II, p 384.
Use: Manuf dyes and intermediates; some dyes derived from it are used as antiseptics, e.g. 9-aminoacridine, acriflavine and proflavine. The hydrochloride has been used as reagent for cobalt, iron and zinc.
Acriflavine Acrilan? Acrinathrin Acrisorcin Acrivastine

Acridine
Acridine chemical structure.png
Identifiers
CAS number 260-94-6 YesY
PubChem 9215
ChemSpider 8860 YesY
ChEBI CHEBI:36420 YesY
ChEMBL CHEMBL39677 YesY
Jmol-3D images Image 1
Image 2
Properties
Molecular formula C13H9N
Molar mass 179.22 g mol−1
Melting point 107 °C; 225 °F; 380 K
Boiling point 346 °C; 655 °F; 619 K
Acidity (pKa) 5.60[1]
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Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
Infobox references

Acridine, C13H9N, is an organic compound and a nitrogen heterocycle. Acridine is also used to describe compounds containing the C13N tricycle.

Acridine is structurally related to anthracene with one of the central CH groups is replaced by nitrogen. Acridine, a colorless solid, was first isolated from coal tar. It is a raw material used for the production of dyes and some valuable drugs. Many acridines, such as proflavine, also have antiseptic properties. Acridine and related derivatives bind to DNA and RNA due to their abilities to intercalate. Acridine orange (3,6-dimethylaminoacridine) is a nucleic acid-selective metachromatic stain useful for cell cycle determination. Acridarsine is formally derived from acridine by replacing the nitrogen atom with one of arsenic, and acridophosphine by replacing it with one of phosphorus.