| Identification | More | [Name]
Acridine | [CAS]
260-94-6 | [Synonyms]
ACRIDINE
DIBENZO[B,E]PYRIDINE
10-Azaanthracene
2,3,5,6-dibenzopyridine
2,3-Benzoquinoline
9-Azaanthracene
Aceridine
Acrydine
Akridin
benzo(b)quinoline
Benzo[b]quinoline
Coal tar pitch volatiles:acridine
coaltarpitchvolatiles:acridine
Acridine
Dibenzo[b,e]pyridine
ACRIDINE, FOR FLUORESCENCE
ACRIDINE 97%
Acridine, 98+%
Acridine Zone Refined (number of passes:45) | [EINECS(EC#)]
205-971-6 | [Molecular Formula]
C13H9N | [MDL Number]
MFCD00005025 | [Molecular Weight]
179.22 | [MOL File]
260-94-6.mol |
| Questions And Answer | Back Directory | [Applications]
Several dyes and drugs feature the acridine skeleton. Many acridines, such as proflavine, also have antiseptic properties. Acridine and related derivatives (such as amsacrine) 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.
 | [Reactions]
Acridine displays the reactions expected of an unsaturated N-heterocycle. It undergoes N-alkylation with alkyl iodides to form alkyl acridinium iodides, which are readily transformed by the action of alkaline potassium ferricyanide to N-alkyl acridones.
Basicity
Acridine and its homologues are weakly basic. Acridine is a photobase which has a ground state pKa of 5.1, similar to that of pyridine, and an excited state pKa of 10.6. It also shares properties with quinoline.
Reduction and oxidation
Acridines can be reduced to the 9,10-dihydroacridines, sometimes called leuco acridines. Reaction with potassium cyanide gives the 9-cyano-9,10-dehydro derivative. On oxidation with potassium permanganate, it yields acridinic acid (C9H5N(CO2H)2) otherwise known as quinoline-1,2-dicarboxylic acid. Acridine is easily oxidized by peroxymonosulfuric acid to the acridine amine oxide. The carbon 9-position of acridine is activated for addition reactions.
|
| Chemical Properties | Back Directory | [Appearance]
colourless to light yellow crystals | [Melting point ]
106-109 °C
| [Boiling point ]
346 °C(lit.)
| [density ]
1,005 g/cm3 | [refractive index ]
1.7270 (estimate) | [Fp ]
346°C | [storage temp. ]
Refrigerator | [solubility ]
dioxane: 0.1 g/mL, clear
| [form ]
Crystalline Powder | [pka]
5.58(at 20℃) | [color ]
Yellow to yellow-brown | [PH Range]
Green B uorescence (5.2) to violet B uorescence (6.6) | [Stability:]
Stable. Combustible. Incompatible with strong oxidizing agents. | [Water Solubility ]
57.35mg/L(24 ºC) | [λmax]
358nm, 392nm | [Merck ]
14,122 | [BRN ]
120200 | [Exposure limits]
OSHA: TWA 0.2 mg/m3 | [Major Application]
Organic light-emitting diode, photoresists, nanosensors, fuel cells, memory device, semiconductors, information storage device, liquid crystal displays, identification of product forgeries, inks, adhesives, textile, hair dyes, gene detection assay, staining cells, biosensors, detecting nucleic acids, proteins, antiHCV antibodies, antibacterial, antiamyloid agents, wound dressing materials, vaccines against infection, allergy and cancer | [InChIKey]
DZBUGLKDJFMEHC-UHFFFAOYSA-N | [LogP]
3.400 | [CAS DataBase Reference]
260-94-6(CAS DataBase Reference) | [EPA Substance Registry System]
Acridine (260-94-6) |
| Safety Data | Back Directory | [Hazard Codes ]
Xn | [Risk Statements ]
R22:Harmful if swallowed. | [Safety Statements ]
S22:Do not breathe dust .
S36:Wear suitable protective clothing . | [RIDADR ]
UN 2713 6.1/PG 3
| [WGK Germany ]
3
| [RTECS ]
AR7175000
| [TSCA ]
Yes | [HazardClass ]
6.1 | [PackingGroup ]
III | [HS Code ]
29333990 | [Safety Profile]
Poison by ingestion, subcutaneous, and intravenous routes. Mutation data reported. A skin, eye, and mucous membrane irritant. When heated to decomposition it emits toxic fumes of NO,. | [Hazardous Substances Data]
260-94-6(Hazardous Substances Data) | [Toxicity]
LD50 s.c. in mice: 0.40 g/kg (Rubbo) |
| Hazard Information | Back Directory | [General Description]
Small colorless needle-like crystalline solid. Slightly soluble in hot water. Slightly denser than water. Contact may irritate skin, eyes, and mucous membranes. Sublimes before melting when heated. May be toxic by ingestion. | [Reactivity Profile]
ACRIDINE(260-94-6) neutralizes acids in exothermic reactions to form salts plus water. May be incompatible with isocyanates, halogenated organics, peroxides, phenols (acidic), epoxides, anhydrides, and acid halides. Flammable gaseous hydrogen may be generated in combination with strong reducing agents, such as hydrides. Burns to give toxic oxides of nitrogen. | [Air & Water Reactions]
Slightly soluble in hot water. | [Health Hazard]
Inhalation irritates respiratory system and causes sneezing, crying, and vomiting. Contact with liquid irritates eyes, skin, and mucous membranes. At high temperature and during sun exposure, damage to the cornea, skin, and mucous membranes may occur following the liberation of acridine vapor. | [Potential Exposure]
Acridine and its derivatives are widely used in the production of dyestuffs, such as acriflavine, benzoflavine, and chrysaniline; and in the synthesis of pharmaceuticals; such as aurinacrine, proflavine, and rivanol. A constituent of coal tar, coal tar creosote; found in wastes from gas and tar plants and coke oven emissions. Incompatibilities: Strong acids, strong oxidizers. | [First aid]
If this chemical gets into the eyes, remove any contact lenses at once and irrigate immediately for at least 15 minutes, occasionally lifting upper and lower lids. If this chemical contacts the skin, remove contaminated clothing and wash immediately with soap and water. When this chemical has been swallowed, get medical attention. Give large quantities of water and induce vomiting. Do not make an unconscious person vomit. If this chemical has been inhaled, remove from exposure and transfer promptly to a medical facility. | [Shipping]
UN2713 Acridine, Hazard Class: 6.1; Labels: 6.1-Poisonous materials | [Incompatibilities]
Acridine and its derivatives are widely used in the production of dyestuffs, such as acriflavine, benzoflavine, and chrysaniline; and in the synthesis of pharmaceuticals; such as aurinacrine, proflavine, and rivanol. A constituent of coal tar, coal tar creosote; found in wastes from gas and tar plants and coke oven emissions. Incompatibilities: Strong acids, strong oxidizers. | [Chemical Properties]
colourless to light yellow crystals | [Waste Disposal]
Incineration with nitrogen oxide removal from the effluent gas by scrubber, catalytic, or thermal device. | [Uses]
A quinoline derivative used as manufacturing dyes and as intermediate for antileishmanial agents. A catabolic product of carbamazepine (C175840) metabolite.
| [Uses]
manufacture of 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. | [Definition]
A colorless
crystalline heterocyclic compound
with three fused rings. Derivatives of acridine
are used as dyes and biological stains. | [Definition]
acridine: A colourless crystallineheterocyclic compound, C12H9N; m.p.110°C. The ring structure is similarto that of anthracene, with threefused rings, the centre ring containinga nitrogen heteroatom. Severalderivatives of acridine (such as acridineorange) are used as dyes or biologicalstains. | [Definition]
ChEBI: A polycyclic heteroarene that is anthracene in which one of the central CH groups is replaced by a nitrogen atom. | [Brand name]
Euflavin;Proflavin. | [World Health Organization (WHO)]
Acridine derivatives with antiseptic and disinfectant activity,
including acriflavine, proflavine and euflavine, were formerly used in the treatment
of infected wounds and burns. Such use has largely been discontinued on the
grounds that safer and more effective alternatives are now available. Following
demonstration of the mutagenic activity of proflavine in 1978 it was withdrawn from dental products in Denmark. Subsequently, euflavine was similarly withdrawn. | [Synthesis Reference(s)]
The Journal of Organic Chemistry, 21, p. 1286, 1956 DOI: 10.1021/jo01117a019
Synthesis, p. 732, 1987 DOI: 10.1055/s-1987-28066 | [Purification Methods]
Acridine has been crystallised twice from *benzene/cyclohexane, or from aqueous EtOH, then sublimed, removing and discarding the first 25% of the sublimate. The remainder is again crystallised and sublimed, discarding the first 10-15% [Wolf & Anderson J Am Chem Soc 77 1608 1955]. Acridine can also be purified by crystallisation from n-heptane and then from ethanol/water after pre-treatment with activated charcoal, or by chromatography on alumina with pet ether in a darkened room. Alternatively, acridine can be precipitated as the hydrochloride from *benzene solution by adding HCl, after which the base is regenerated, dried at 110o/50mm, and recrystallised to constant melting point from pet ether [Cumper et al. J Chem Soc 4518 1962]. The regenerated free base may be recrystallised, chromatographed on basic alumina, then vacuum-sublimed and zone-refined. [Williams & Clarke, J Chem Soc, Faraday Trans 1 73 514 1977, Albert, The Acridines Arnold Press 1966.] It can exist in five crystalline forms and is steam volatile. It is a strong IRRITANT to skin and mucous membranes and can become a chronic irritant— handle it with CARE. [Beilstein 20/8 V 199.] |
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