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Acridine

Applications Reactions
Acridine
Acridine structure
CAS No.
260-94-6
Chemical Name:
Acridine
Synonyms
Akridin;Acrydine;ACRIDINE;NSC 3408;Aceridine;Acridine >ACRIDINE 97%;Acridine, 98+%;9-Azaanthracene;10-Azaanthracene
CBNumber:
CB9853399
Molecular Formula:
C13H9N
Formula Weight:
179.22
MOL File:
260-94-6.mol

Acridine Properties

Melting point:
106-109 °C
Boiling point:
346 °C(lit.)
Density 
1,005 g/cm3
refractive index 
1.7270 (estimate)
Flash point:
346°C
storage temp. 
Refrigerator
solubility 
dioxane: 0.1 g/mL, clear
pka
5.58(at 20℃)
form 
Crystalline Powder
color 
Yellow to yellow-brown
PH Range
Green B uorescence (5.2) to violet B uorescence (6.6)
Water Solubility 
57.35mg/L(24 ºC)
λmax
358nm, 392nm
Merck 
14,122
BRN 
120200
Stability:
Stable. Combustible. Incompatible with strong oxidizing agents.
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
CAS DataBase Reference
260-94-6(CAS DataBase Reference)
EWG's Food Scores
1
FDA UNII
42NI1P5Q1X
EPA Substance Registry System
Acridine (260-94-6)
SAFETY
  • Risk and Safety Statements
Symbol(GHS) 
GHS07,GHS08
Signal word  Warning
Hazard statements  H335-H341-H315-H319-H302
Precautionary statements  P264-P270-P280-P301+P312+P330-P302+P352+P332+P313+P362+P364-P305+P351+P338+P337+P313-P501-P201-P261-P305+P351+P338-P405-P501a
Hazard Codes  Xn
Risk Statements  22-68-36/37/38
Safety Statements  22-36-45-36/37/39-26
RIDADR  UN 2713 6.1/PG 3
WGK Germany  3
RTECS  AR7175000
TSCA  Yes
HazardClass  6.1
PackingGroup  III
HS Code  29333990
Toxicity LD50 s.c. in mice: 0.40 g/kg (Rubbo)

Acridine price More Price(32)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Sigma-Aldrich 01640 Acridine BioReagent, suitable for fluorescence, ≥97.0% (HPLC) 260-94-6 1g $40.6 2021-12-16 Buy
Sigma-Aldrich 01640 Acridine BioReagent, suitable for fluorescence, ≥97.0% (HPLC) 260-94-6 10g $95.9 2021-12-16 Buy
TCI Chemical A0129 Acridine Zone Refined (number of passes:45) >99.0%(HPLC)(T) 260-94-6 1sample $245 2021-12-16 Buy
TCI Chemical A0294 Acridine >98.0%(HPLC)(T) 260-94-6 5g $154 2021-12-16 Buy
Alfa Aesar L01657 Acridine, 97% 260-94-6 25g $199 2021-12-16 Buy

Acridine Chemical Properties,Uses,Production

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

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

ChEBI: A polycyclic heteroarene that is anthracene in which one of the central CH groups is replaced by a nitrogen atom.

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.

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

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.

Acridine synthesis

95888-33-8
260-94-6
Synthesis of Acridine from Benzaldehyde, 2-(phenylamino)-

Acridine Preparation Products And Raw materials

Raw materials

Preparation Products


Acridine Suppliers

Global( 172)Suppliers
Supplier Tel Fax Email Country ProdList Advantage
Zhengzhou Yuanli Biological Technology Co., Ltd
0086-371-67897895
info@zzyuanli.cn CHINA 136 58
Wuhan KEMI-WORKS Chemical Co., Ltd.

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Hangzhou FandaChem Co.,Ltd.
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career henan chemical co
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HENAN BON INDUSTRIAL CO.,LTD
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View Lastest Price from Acridine manufacturers

Image Release date Product Price Min. Order Purity Supply Ability Manufacturer
2021-11-02 Acridine
260-94-6
US $65.00 / g 5g 99% 100kg Baoji Guokang Healthchem co.,ltd
2021-07-20 Acridine
260-94-6
US $0.00-0.00 / KG 1g 99% 2000tons Shaanxi Dideu Medichem Co. Ltd
2019-07-06 Acridine
260-94-6
US $1.00 / KG 1G 99% 100kg Career Henan Chemical Co

Acridine Spectrum


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