4395-65-7

Usage

Uses

Used in Textile Industry:
1-AMINO-4-ANILINOANTHRAQUINONE is used as a dye for textiles due to its color properties and solubility in various solvents. It provides good ironing fastness, light fastness, perspiration fastness, and washing fastness, making it suitable for various textile applications.
Used in Colorant Industry:
1-AMINO-4-ANILINOANTHRAQUINONE is used as a colorant in various industries, such as plastics, coatings, and inks, due to its vibrant color and solubility in different solvents.
The provided materials indicate that 1-AMINO-4-ANILINOANTHRAQUINONE has a rating of 4 for ironing fastness, 3 for light fastness, 5 for perspiration fastness, 5 for washing fastness, 5 for fading, and a rating between 4-5 for staining. These ratings are based on the ISO standard.

Preparation

1-Amino-4-hydroxyanthfacene-9,10-dione?with aniline in the presence of boric acid in condensation.

Standard

Ironing Fastness

Fading

Stain

ISO

4

InChI:InChI=1/C20H14N2O2/c21-15-10-11-16(22-12-6-2-1-3-7-12)18-17(15)19(23)13-8-4-5-9-14(13)20(18)24/h1-11,22H,21H2

Upstream product

• 116-81-4 1-amino-4-bromo-9,10-dioxoanthracene-2-sulphonic acid 
• 62-53-3 aniline 
• 116-85-8 4-hydroxy-1-aminoanthraquinone 
• 116-83-6 1-amino-4-methoxyanthraquinone 
• 2872-47-1 1-amino-4-chloroanthraquinone 
• 2786-71-2 1-amino-4-anilino-9,10-dioxo-9,10-dihydro-anthracene-2-sulfonic acid 
• 70730-92-6 5-chloro-6H-anthra[1,9-cd]isoxazol-6-one 
• 98-82-8 Isopropylbenzene 
• 70730-76-6 5-anilino-anthra[1,9-cd]isoxazol-6-one 
• 81-62-9 1-amino-4-bromo-9,10-anthracenedione 
• 13460-50-9 metaboric acid 
• 6258-06-6 sodium 1-amino-4-bromoanthraquinone-2-sulfonate 
• 74386-36-0 1-azido-4-chloro-anthraquinone 

Downstream Products

• 103566-97-8 furan-2,5-dicarboxylic acid bis-(4-anilino-9,10-dioxo-9,10-dihydro-[1]anthrylamide) 
• 32571-82-7 1-Amino-9,10-dioxo-4-phenylamino-9,10-dihydroanthracen-2-carbonitril 
• 201941-62-0 [Ru(Cl)(C₆H₄(CH₃)(CH(CH₃)2))(C₆H₄(CO)2C₆H₂(NHC₆H₅)NH)] 
• 201941-64-2 [PdCl(PEt₃)(C₆H₄(CO)2C₆H₂(NHC₆H₅)NH)] 
• 201941-63-1 trans-[PtCl(PEt₃)(C₆H₄(CO)2C₆H₂(NHC₆H₅)NH)] 
• 202007-96-3 cis-[PtCl(PEt₃)(C₆H₄(CO)2C₆H₂(NHC₆H₅)NH)] 

Relevant academic research and scientific papers

Synthesis of -s-triazine Derivatives

The disperse dyes of the type -s-triazine derivatives have been synthesized by condensation of bromamine acid with aniline, then desulphonation and cyclisation to obtained 8-aminoceramidone, followed by its cyanuration and condensation with various aryl urea.The dyeing properties of these dyes were studied on polyester fabrics.

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.

Arylamination of Aminohalogenoanthraquinones

1-Amino-4-arylaminoanthraquinones (II) have been prepared in high yields by reacting 1-amino-4-chloroanthraquinone (Ia, 1 mol) with arylamines (6 mol) and anhyd.AlCl3 (5 mol) in nitrobenzene at room temperature. 1-Amino-2-bromoanthraquinone, 2-amino-1-chloroanthraquinone, 1-benzamido-4-chloroanthraquinone and 1-amino-5-chloroanthraquinone fail to give arylaminated products. 1-Amino-2,4-dibromoanthraquinone (Ic) gives only 4-arylaminated compounds (IIq-s) whereas 1-amino-8-chloroanthraquinone (Ie) gives 2-arylaminated derivatives (III).A plausible mechanism for the reaction has been suggested.The arylaminated compounds have been applied on polyester as disperse dyes and their dyeing properties evaluated.

INSERTION OF 1-NITRENOANTRAQUINONES AT C-H BOND

The thermolysis of anthraoxazol-6-ones in cumene and p-cymene leads to insertion of the obtained nitrene at the C-H bond and also to reduction of the nitrene to a primary amine.

AMINATION OF ANTHRAISOXAZOL-6-ONES

The behavior of 3,5-dihalo derivatives of anthraisoxazol-6-one with respect to primary and secondary amines was studied. 5-Chloroanthraisoxazol-6-one undergoes amination particularly readily.The products of the reaction of isoxazoles with amines are the corresponding amino derivatives.The amination of 5-chloroanthraisoxazol-6-one in refluxing dimethylformamide (DMF) is accompanied by reductive cleavage of the isoxazole ring and the formation of 1-amino-4-arylaminoanthraquinones.Amination in the 5 position with substitution of a hydride ion takes place primarily in the reaction of 3-chloroanthraisoxazol-6-one with benzylamine or cyclohexylamine, whereas the chlorine in the 3 position is replaced by the action of morpholine or piperidine on the same substrate.