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Acridine

Acridine
Acridine chemical structure
Names
Preferred IUPAC name
Acridine
Other names
Dibenzo[b,e]pyridine
2,3-Benzoquinoline
Identifiers
260-94-6 YesY
3D model (Jmol) Interactive image
Interactive image
ChEBI CHEBI:36420 YesY
ChEMBL ChEMBL39677 YesY
ChemSpider 8860 YesY
ECHA InfoCard 100.005.429
EC Number 205-971-6
PubChem 9215
RTECS number AR7175000
Properties
C13H9N
Molar mass 179.22 g·mol−1
Appearance White powder
Odor Irritating
Density 1.005 g/cm3 (20 °C)
Melting point 106–110 °C (223–230 °F; 379–383 K)
at 760 mmHg
Boiling point 344.86 °C (652.75 °F; 618.01 K)
at 760 mmHg
46.5 mg/L
Solubility Soluble in CCl4, alcohols, (C2H5)2O, C6H6
log P 3.4
Vapor pressure 0.34 kPa (150 °C)
2.39 kPa (200 °C)
11.13 kPa (250 °C)
Acidity (pKa) 5.58 (20 °C)
UV-vis (λmax) 392 nm
-123.3·10−6 cm3/mol
Thermochemistry
205.07 J/mol·K
208.03 J/mol·K
179.4 kJ/mol
6581.3 kJ/mol
Hazards
GHS pictograms The exclamation-mark pictogram in the Globally Harmonized System of Classification and Labelling of Chemicals (GHS)
GHS signal word Danger
H302
Harmful Xn
R-phrases R22, R36/37/38
S-phrases (S2), S24/25, S36
NFPA 704
Flammability code 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g., canola oil Health code 2: Intense or continued but not chronic exposure could cause temporary incapacitation or possible residual injury. E.g., chloroform Reactivity code 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g., liquid nitrogen Special hazards (white): no codeNFPA 704 four-colored diamond
Lethal dose or concentration (LD, LC):
LD50 (median dose)
 500 mg/kg (mice, oral)
US health exposure limits (NIOSH):
PEL (Permissible)
 TWA 0.2 mg/m3 (benzene-soluble fraction)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
YesY  (what is YesYN ?)
Infobox references

Acridine is an organic compound and a nitrogen heterocycle with the formula C13H9N. Acridines are substituted derivatives of the parent ring. It is a planar molecule that is structurally related to anthracene with one of the central CH groups replaced by nitrogen. Like the related molecule pyridine and quinoline, acridine is mildly basic. It is an almost colorless solid. There are no commercial applications of acridines but at one time acridine dyes were popular. It crystallizes in needles.

Carl Gräbe and Heinrich Caro first isolated acridine in 1870 from coal tar. Acridine is separated from coal tar by extracting with dilute sulfuric acid. Addition of potassium dichromate to this solution precipitates acridine bichromate. The bichromate is decomposed using ammonia.

Acridine and its derivatives can be prepared by many synthetic processes. In the Bernthsen acridine synthesis, diphenylamine is condensed with carboxylic acids in the presence of zinc chloride. When formic acid is the carboxylic acid, the reaction yields the parent acridine. With the higher larger carboxylic acids, the derivatives substituted at the meso carbon atom are generated.

Other older methods for the organic synthesis of acridines include condensing diphenylamine with chloroform in the presence of aluminium chloride, by passing the vapours of orthoaminodiphenylmethane over heated litharge, by heating salicylaldehyde with aniline and zinc chloride or by distilling acridone (9-position a carbonyl group) over zinc dust. Another classic method for the synthesis of acridones is the Lehmstedt-Tanasescu reaction.


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