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260-94-6

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260-94-6 Usage

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

colourless to light yellow crystals

Uses

Different sources of media describe the Uses of 260-94-6 differently. You can refer to the following data:
1. A quinoline derivative used as manufacturing dyes and as intermediate for antileishmanial agents. A catabolic product of carbamazepine (C175840) metabolite.
2. 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.
3. Acridine is a compound occurring in coal tar that has been used in the manufacture of dyes and intermediates. Derivatives are used as antiseptics (e.g., proflavine). Acridine is a strong irritant to mucous membranes and skin, and it causes sneezing on inhalation.

Definition

Different sources of media describe the Definition of 260-94-6 differently. You can refer to the following data:
1. ChEBI: A polycyclic heteroarene that is anthracene in which one of the central CH groups is replaced by a nitrogen atom.
2. A colorless crystalline heterocyclic compound with three fused rings. Derivatives of acridine are used as dyes and biological stains.
3. 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.

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/jo01117a019Synthesis, p. 732, 1987 DOI: 10.1055/s-1987-28066

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.

Air & Water Reactions

Slightly soluble in hot water.

Reactivity Profile

Acridine 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.

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.

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,.

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.

Shipping

UN2713 Acridine, Hazard Class: 6.1; Labels: 6.1-Poisonous materials

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.]

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.

Waste Disposal

Incineration with nitrogen oxide removal from the effluent gas by scrubber, catalytic, or thermal device.

Check Digit Verification of cas no

The CAS Registry Mumber 260-94-6 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 2,6 and 0 respectively; the second part has 2 digits, 9 and 4 respectively.
Calculate Digit Verification of CAS Registry Number 260-94:
(5*2)+(4*6)+(3*0)+(2*9)+(1*4)=56
56 % 10 = 6
So 260-94-6 is a valid CAS Registry Number.
InChI:InChI=1/C13H9N/c1-3-7-12-10(5-1)9-11-6-2-4-8-13(11)14-12/h1-9H

260-94-6 Well-known Company Product Price

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  • Alfa Aesar

  • (L01657)  Acridine, 97%   

  • 260-94-6

  • 5g

  • 626.0CNY

  • Detail
  • Alfa Aesar

  • (L01657)  Acridine, 97%   

  • 260-94-6

  • 25g

  • 2087.0CNY

  • Detail

260-94-6SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 11, 2017

Revision Date: Aug 11, 2017

1.Identification

1.1 GHS Product identifier

Product name acridine

1.2 Other means of identification

Product number -
Other names Acrydine

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:260-94-6 SDS

260-94-6Relevant articles and documents

N-H Bond Formation in a Manganese(V) Nitride Yields Ammonia by Light-Driven Proton-Coupled Electron Transfer

Wang, Dian,Loose, Florian,Chirik, Paul J.,Knowles, Robert R.

, p. 4795 - 4799 (2019)

A method for the reduction of a manganese nitride to ammonia is reported, where light-driven proton-coupled electron transfer enables the formation of weak N - H bonds. Photoreduction of (saltBu)MnVN to ammonia and a Mn(II) complex has been accomplished using 9,10-dihydroacridine and a combination of an appropriately matched photoredox catalyst and weak Br?nsted acid. Acid-reductant pairs with effective bond dissociation free energies between 35 and 46 kcal/mol exhibited high efficiencies. This light-driven method may provide a blueprint for new approaches to catalytic homogeneous ammonia synthesis under ambient conditions.

Castellano et al.

, p. 3508,3511 (1973)

Copper-catalyzed aerobic oxidative C-H and C-C functionalization of 1-[2-(Arylamino)aryl]ethanones leading to acridone derivatives

Yu, Jipan,Yang, Haijun,Jiang, Yuyang,Fu, Hua

, p. 4271 - 4277 (2013)

Efficient copper-catalyzed aerobic oxidative C-H and C-C functionalization of 1-[2-(arylamino)aryl]ethanones leading to acridones has been developed. The procedure involves cleavage of aromatic C-H and acetyl C-C bonds with intramolecular formation of a diarylketone bond. The protocol uses inexpensive Cu(O2CCF3)2 as catalyst, pyridine as additive, and economical and environmentally friendly oxygen as the oxidant, and the corresponding acridones with various functional groups were obtained in moderate to good yields. Acridone synthesis: Efficient copper-catalyzed aerobic oxidative C-H and C-C functionalization of 1-[2-(arylamino)aryl]ethanones leading to acridones has been developed. The procedure involves cleavage of aromatic C-H and acetyl C-C bonds with intramolecular formation of a diarylketone bond (see scheme). The protocol uses inexpensive Cu(O 2CCF3)2 as catalyst, pyridine as additive, and economical and environmentally friendly oxygen as oxidant. The corresponding acridones with various functional groups were obtained in moderate to good yields. Copyright

Formation of Acridine from the Reaction of Dibenzazepine with Silver(I): Formation of an Aromatic Nitrenium Ion ?

Cann, Michael C.

, p. 1112 - 1113 (1988)

-

A Simple Route to C-Functionalised Azaxylylenes and Diazaxylylenes

Fishwick, Colin W. G.,Storr, Richard C.,Manley, Paul W.

, p. 1304 - 1305 (1984)

o-Lithiation of t-butoxycarbonylaniline and 4-t-butoxycarbonylaminopyridine followed by reaction with aldehydes gives t-butoxycarbonylamino alcohols which are converted into azaxylylenes and diazaxylylenes on flash pyrolysis.

Oxidation of N-methyl-9-t-butylacridane by iodosylbenzene catalyzed by tetrakis(pentafluorophenyl) porphyrin iron(III). A tool to investigate the mechanism of the oxidative N-demethylation of aromatic tertiary amines

Baciocchi, Enrico,Lapi, Andrea

, p. 5425 - 5428 (1999)

The PhIO promoted oxidation of N-methyl-9-t-butylacridane (1) catalyzed by tetrakis(pentafluorophenyl) porphyrin iron(III) leads first to 9-t- butylacridane and then to acridine. It is suggested that 1 can represent a reliable machanistic probe to detect the intervention of radical cations in the oxidation of aromatic amines.

-

Bernardi et al.

, p. 3575,3580 (1971)

-

Photocatalytic degradation of antiepileptic drug carbamazepine with bismuth oxychlorides (BiOCl and BiOCl/AgCl composite) in water: Efficiency evaluation and elucidation degradation pathways

Meribout, Rayene,Zuo, Ying,Khodja, Amina Amine,Piram, Anne,Lebarillier, Stéphanie,Cheng, Jiushan,Wang, Cong,Wong-Wah-Chung, Pascal

, p. 105 - 113 (2016)

The heterogeneous photocatalytic degradation of carbamazepine (CBZ) was investigated in the presence of BiOCl/AgCl composite photocatalyst under simulated sunlight irradiation in water. BiOCl/AgCl composite showed higher photocatalytic activity than pure BiOCl for CBZ degradation. The photocatalytic mechanism analysis was based on byproducts identification by LC–MS-QTof and active species trapping or inhibiting experiments. The results revealed that the first step of the transformation mainly results in an electron transfer implying positive holes and to a lesser extent in hydroxyl radical's involvement. The enhanced photocatalytic performance of BiOCl/AgCl was proved to be related to the suitable conduction and valence band interaction that extends optical response range but also improves the efficient separation of photoinduced electron-hole pairs. BiOCl/AgCl composite totally removed CBZ from natural surface water after 30?min irradiation, suggesting its potential application to wastewater treatments. Eight intermediate products were identified demonstrating that CBZ transformation occurs through two main routes from CBZ radical cation, hydroxylation of ring (aromatic or seven membered rings), followed by further oxidation, rearrangement ring and hydroxylation.

New Gas Phase Reactions of Substituted Benzyl, Phenylaminyl, and Phenoxyl Radicals. Rearrangements to Fused 5- and 6-Membered Heterocyclic Systems

Cadogan, J. I. G.,Hickson, Clare L.,Hutchison, H. Susan,McNab, Hamish

, p. 643 - 644 (1985)

Flash vacuum pyrolysis studies of substituted benzyl, phenylaminyl, and phenoxyl radicals have revealed three new classes of reactions: formation of five-membered ring products via intramolecular abstracion of an aromatic hydrogen atom, formation of six-membered rings via spirodienyl radical intermediates, and isomerisation of o-phenoxybenzyl into o-benzylphenoxyl radicals and vice versa.

Visible-light-mediated organoboron-catalysed metal-free dehydrogenation of N-heterocycles using molecular oxygen

Wei, Lanfeng,Wei, Yu,Xu, Liang,Zhang, Jinli

supporting information, p. 4446 - 4450 (2021/06/30)

The surge of photocatalytic transformation not only provides unprecedented synthetic methods, but also triggers the enthusiasm for more sustainable photocatalysts. On the other hand, oxygen is an ideal oxidant in terms of atom economy and environmental friendliness. However, the poor reactivity of oxygen at the ground state makes its utilization challenging. Herein, a visible-light-induced oxidative dehydrogenative process is disclosed, which uses an organoboron compound as the photocatalyst and molecular oxygen as the sole oxidant.Viathis approach, an array of N-heterocycles have been accessed under metal-free mild conditions, in good to excellent yields.

Iron(II)-Catalyzed Aerobic Biomimetic Oxidation of N-Heterocycles

Manna, Srimanta,Kong, Wei-Jun,B?ckvall, Jan-E.

supporting information, p. 13725 - 13729 (2021/09/08)

Herein, an iron(II)-catalyzed biomimetic oxidation of N-heterocycles under aerobic conditions is described. The dehydrogenation process, involving several electron-transfer steps, is inspired by oxidations occurring in the respiratory chain. An environmentally friendly and inexpensive iron catalyst together with a hydroquinone/cobalt Schiff base hybrid catalyst as electron-transfer mediator were used for the substrate-selective dehydrogenation reaction of various N-heterocycles. The method shows a broad substrate scope and delivers important heterocycles in good-to-excellent yields.

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