116-85-8

Usage

Chemical Properties

deep purple to dark brown crystalline powder

Uses

The use of the inclusion complex of 1-amino-4-hydroxyanthraquinone (AHA) in the internal cavity of β-cyclodextrin confers increased sensitivity, selectivity and detection limit, and allows the determination of 10-70 ng ml-1 beryllium, compared to 60-500 ng ml-1 in the absence of the cyclodextrin.

Safety Profile

Poison by intravenous route. Moderately toxic by intraperitoneal route. Mutation data reported. When heated to decomposition it emits toxic fumes of NOx,.

Properties and Applications

blue light pink to red blue light. Soluble in acetone, ethanol, benzene and linseed oil. The strong sulfuric acid to dark yellow, diluted for brown. Used in vinegar fiber, three vinegar, polyamide, polyester fiber, acrylic dyeing, also can be used for sheep and plastic color. Levelness and promote good rate. Standard Ironing Fastness Light Fastness Persperation Fastness Washing Fastness Fading Stain Fading Stain Fading Stain ISO 4 2 5-6 5 5 3-4 4

Standard

Ironing Fastness

Fading

Stain

ISO

4

Purification Methods

Purify it by TLC on SiO2 gel plates (0.75mm thick) using toluene/acetone (9:1) as eluent. The main band is scraped off and extracted with MeOH. The solvent is evaporated, and the dye is dried in a drying pistol [Land et al. J Chem Soc, Faraday Trans 1 72 2091 1976]. It has also been recrystallised from aqueous EtOH. [Beilstein 14 H 268, 14 I 503, 14 II 168, 14 III 652, 14 IV 891.]

InChI:InChI=1/C14H9NO3/c15-9-5-6-10(16)12-11(9)13(17)7-3-1-2-4-8(7)14(12)18/h1-6,16H,15H2

Upstream product

• 85-44-9 phthalic anhydride 
• 123-30-8 4-amino-phenol 
• 42013-62-7 1-azidoanthracene-9,10-dione 
• 16048-40-1 9,10-dioxo-1-anthracenediazonium 
• 82-34-8 1-nitroanthraquinone 
• 81-64-1 1,4-dihydroxy-9,10-anthracenedione 
• 81-62-9 1-amino-4-bromo-9,10-anthracenedione 
• 56613-39-9 1-hydroxylaminoanthraquinone 
• 5327-72-0 1,4-diamino-anthracene-9,10-diol 
• 82-45-1 1-amino-9,10-anthracenedione 
• 52603-35-7 2-(3-bromo-5-aminobenzoyl)benzoic acid 
• 70730-89-1 6H-anthra<1,9-cd>isoxazol-6-one 
• 7664-93-9 sulfuric acid 
• 13460-50-9 metaboric acid 

Downstream Products

• 7323-62-8 4-Acetylamino-1-hydroxy-9,10-anthracenedione 
• 116-82-5 1-amino-2-bromo-4-hydroxyanthraquinone 
• 129-43-1 1-hydroxyanthraquinone 
• 81-64-1 1,4-dihydroxy-9,10-anthracenedione 
• 6373-16-6 1-methylamino-4-hydroxyanthraquinone 
• 24929-02-0 1-amino-4-hydroxy-9,10-dioxo-9,10-dihydroanthracene-2-sulfonic acid 
• 6313-46-8 1-amino-4-hydroxy-2-mercapto-anthraquinone 
• 10150-19-3 1-(4-Hydroxy-9,10-dioxo-9,10-dihydro-anthracen-1-yl)-3-phenyl-urea 
• 112128-54-8 C₂₈H₁₉N₃O₅ 
• 116-83-6 1-amino-4-methoxyanthraquinone 
• 39774-73-7 1-amino-4-p-tolylaminoanthraquinone 
• 6409-74-1 N-(4-hydroxy-9,10-dioxo-9,10-dihydro-[1]anthryl)-benzamide 
• 65121-98-4 (4-hydroxy-9,10-dioxo-9,10-dihydro-[1]anthryl)-carbamic acid ethyl ester 
• 1310827-72-5 4-(4-amino-9,10-dioxo-9,10-dihydroanthracen-1-ylamino)phenyl methacrylate 

Relevant academic research and scientific papers

A facile method for preparing substituted 1-aminoanthraquinones

An efficient and simple preparation of α-substituted aminoanthraquinones using 2,2,-dialkoxyethylamines is described.

Kinetic Studies on the Amination of Leucoquinizarin

Leucoquinizarin reacts with amines to give mono- and diaminoanthraquinones.The amination mechanism of leucoquinizarin was investigated on the basis of the kinetics and structures of leuco compounds.The amination reaction of leucoquinizarin was characterized as follows.This amination proceeded in polar solvent but not in nonpolar solvent at all.The reaction rate was not influenced by the addition of a small amount of water (95percent ethanol) but enhanced largely in 80percent ethanol.This amination reaction has a low activation energy (ΔE=5.7-9.0 kcal mol-1) and an extraordinarily small pre-exponential term (A=103 - 105 mol-1min-1).Leucoquinizarin was proposed to be aminated by the addition of amine to carboynl group at its 1,4-position.The oxidation of leuco monoaminohydroxyanthraquinone was also examined.

Antitumor Agents-CLXVII. Synthesis and structure-activity correlations of the cytotoxic anthraquinone 1,4-bis-(2,3-epoxypropylamino)-9,10-anthracenedione, and of related compounds

1,4-Bis-(2,3-epoxypropylamino)-9,10-anthracenedione (3) was synthesized in this laboratory and was found to be a potent antitumor agent. Derivatives of this compound containing anthraquinone, naphthoquinone, and quinone skeletons were also prepared and evaluated for in vitro cytotoxic activity in several cell lines. These molecules were designed as bifunctional antitumor agents with the potential to act as (1) intercalating agents due to their planar backbones, and (2) alkylating agents due to the presence of alkylating moieties in their side chains. Compounds with an anthraquinone skeleton and propylamino side chains containing epoxides or halohydrins as the alkylating species showed greater activity than similar compounds with naphthoquinone or quinone skeletons. Compounds without these alkylating functionalities (e.g., with alkene or amino groups) were generally inactive. Hydroxy substitution on the planar skeleton in conjunction with alkylating side chains gave compounds with the most potent cytotoxic activity. The position of the hydroxy groups and side chains could be varied without substantially affecting activity. Activity was retained when an epoxypropyloxy side chain was substituted for the epoxypropylamino side chain in the parent compound.

COMPOUND, PHOTOSENSITIVE RESIN COMPOSITION COMPRISING THE SAME, PHOTO RESIST, COLOR FILTER, AND DISPLAY DEVICE

The present specification provides a compound represented 1 by chemical formula I, a, photosensitive, resin composition including the same, a color filter, a color filter, and a display. device including the same. (by machine translation)

BROMINATION OF 2-BENZOYLBENZOIC ACIDS

A new method was developed for the synthesis of bromine-substituted 9,10-anthraquinones by bromination of 2-benzoylbenzoic acid derivatives in the presence of sulfuric and nitric acids followed by cyclization.

Selective Photoalkylamination and Photohydroxylation of Aminoantraquinones and their N-Acylated Derivatives

The selective introduction of hydroxy and alkylamino groups into the anthraquinone nucleus was achieved by the photochemical reaction of some aminoantraquinones and their N-acylated derivatives with alkylamines under aerobic conditions.

Kinetics and product studies on Ullmann amination of 1-halogenoanthraquinones catalysed by copper(I)salts in acetonitrile solution

The kinetics and products of reactions of some primary amines (RNH2) with 1-halogenoanthraquininone (AQX) promoted by copper salts, particularly tetrakis(acetonitrile)copper(I) tetrafluoroborate, have been investigated in acetonitrile solution at 70 deg C.Provided that oxygen does not come into contact with solutions of the copper(I) salt and amine, the kinetics of the reactions have the simple form v = k, and the products consist almost entirely of the aminated anthraquinone, AQNHR, and dehalogenated material, AQH, their ratio being directly proportional to .The reaction rate is dependent on the identity of the departing halogen X, decreasing in the sequence I > Br > Cl, but the product ratio is little affected.N-Deuteration of the reactant amine gives rise to a small kinetic isotope effect, but the product ratio is unaffected.Conversely deutearation on the α-carbon atom of the amine has little kinetic effect but leads to a four-fold increase in the ratio of aminated to dehalogenated product.The observations are interpreted in terms of (i) formation of a copper(I)-amine complex, (II) activation of this species for attack on AQX by proton abstraction from an amine ligand by a free molecule (stepwise or concerted), and (iii) generation of an arylcopper(III) intermediate which is partitioned between formation of AQNHR by attack of an externel amine molecule and formation of AQH by an intramolecular process involving hydrogen transfer from the α-carbon atom in the amine ligand generated in (ii).Exposure of the initial copper(I)-amine complex to oxygen leads to a new complex, itself capable of reacting with AQX, which on prolonged incubation at 70 deg C in the presence of an excess of amine is transformed back to its original state.

Synthesis of 2-Chloro-6,11(5H)-morphanthridinedione and Its Rearrangement to 1-Amino-4-hydroxyanthraquinone

p-Nitrochlorobenzene (I) condenses with o-carboxyphenylacetonitrile (II) in methanolic potassium hydroxide to produce 3-(2'-carboxyphenyl)-5-chloro-2,1-benzisoxazole (III).Reduction of III leads to a novel synthesis of 2-chloro-6,11(5H)-morphanthridinedione (V) in good yields.The acid catalysed rearrangement of V affords 1-amino-4-hydroxyanthraquinone (VI).

C-FORMYLATION OF α-PHENYLAMINOANTHRAQUINONES WITH FORMALDEHYDE. REACTION OF α-AMINOANTHRAQUINONES WITH FORMALDEHYDE IN SULFURIC ACID

The reaction of α-phenylaminoanthraquinones with formaldehyde in concentrated sulfuric acid leads to formylation at the para position of the phenyl group.The possibility of extending the reaction to related systems was demonstrated for the case of 6-phenylamino-N-methylanthrapyridone.It is suggested that the intermediate compounds in the C-formylation, N-methylation, and demethylation respectively of α-amino and α-methylaminoanthraquinones are 7H-7-oxoanthra-1,3-oxazinium cations.