117-11-3

Usage

Uses

Used in Textile Industry:
1-Amino-5-chloroanthraquinone is used as a dye intermediate for textile dyeing and printing processes. Its vibrant color and solubility in organic solvents make it an ideal choice for imparting color to fabrics, enhancing their visual appeal and durability.
Used in Art Supplies:
In the art supplies industry, 1-Amino-5-chloroanthraquinone is used as a pigment in the manufacturing of colored pencils. Its bright color and stability contribute to the quality and longevity of these drawing tools, providing artists with a reliable and vibrant medium for their creative expressions.
Used in Printing and Inks:
1-Amino-5-chloroanthraquinone is also utilized in the production of inks, particularly for printing applications. Its colorfastness and compatibility with various printing techniques make it a preferred choice for creating high-quality, long-lasting prints.
Safety Considerations:
Due to its moderate acute toxicity, 1-Amino-5-chloroanthraquinone requires proper handling and storage measures to ensure safe usage and disposal. This includes adhering to safety guidelines, using appropriate protective equipment, and disposing of the chemical in an environmentally responsible manner.

InChI:InChI=1/C14H8ClNO2/c15-9-5-1-3-7-11(9)13(17)8-4-2-6-10(16)12(8)14(7)18/h1-6H,16H2

Upstream product

• 82-44-0 1-chloroanthracene-9,10-dione 
• 82-46-2 1,5-Dichloroanthraquinone 
• 82-50-8 5-nitroanthraquinone-1-sulfonic acid 
• 128-56-3 anthraquinone-1-sulphonic acid sodium salt 
• 93804-31-0 potassium 5-nitroanthraquinone-1-sulfonate 
• 155244-86-3 1-Chloro-5-(2,2-diethoxy-ethylamino)-anthraquinone 
• 82-14-4 N-(5-chloro-9,10-dioxo-9,10-dihydro-[1]anthryl)-toluene-4-sulfonamide 
• 129-40-8 5-chloro-1-nitroanthraquinone 

Downstream Products

• 245064-92-0 1,4-dihydroxy-5-chloro-9,10-anthraquinone 
• 117-05-5 1-Chloro-5-benzoylaminoanthraquinone 
• 861791-83-5 2-(5-chloro-9,10-dioxo-9,10-dihydro-[1]anthrylamino)-benzaldehyde 
• 94544-58-8 1-chloro-5-phenyl-anthraquinone 
• 59261-96-0 Sodium; 1-amino-5-chloro-9,10-dioxo-9,10-dihydro-anthracene-2-sulfonate 
• 138452-36-5 8-Chloro-3,11b-dibenzyl-2-phenyl-3,11b-dihydroanthra<1,9-de>-1,3-oxazin-7(2H)-one 
• 129-43-1 1-hydroxyanthraquinone 
• 66012-06-4 5-Amino-1-<4-tert.butyl-phenoxy>-anthrachinon 
• 85193-22-2 N-(5-chloroanthraquinon-1-yl)triphenylphosphazene 
• 85193-13-1 1-S,S-diphenyl-N-(5-chloroanthraquinon-1-yl)sulfoximide 
• 85193-07-3 1-S-methyl-1-S-phenyl-N-(5-chloroanthraquinon-1-yl)sulfoximide 
• 138452-29-6 7-Benzylamino-1-phenylnaphth<1,2,3-cd>indol-6(2H)-one 
• 138452-25-2 2-Benzyl-7-chloro-1-phenylnaphth<1,2,3-cd>indol-6(2H)one 
• 138452-26-3 7-Chloro-1-phenylnaphth<1,2,3-cd>indol-6(2H)one 

Relevant academic research and scientific papers

Synthesis and cytotoxic activity of 7-oxo-7H-dibenz[f,ij]isoquinoline and 7-oxo-7H-benzo[e]perimidine derivatives

A series of 7-oxo-7H-dibenz[f,ij]isoquinoline and 7-oxo-7H-benzo[e]perimidines bearing cationic side chains were prepared from aminoanthraquinones. The perimidines were prepared from 1-aminoanthraquinone by initial condensation with urea or dimethylacetamide. A series of 2-, 4-, 8-, and 11-carboxy derivatives of the dibenzisoquinolines were prepared from aminoanthraquinonecarboxylic acids. The cationic derivatives were prepared from these via amide, amine, or methylene linkers to study the effects of side chain positioning on biological activity. Within the series of carboxamide-linked compounds, the order of increasing cytotoxicity was 8- 4- 2- 11-. The 2- and 4-carboxamides showed substantial growth delays against in vivo subcutaneous colon 38 tumors in mice, but the 11-carboxamide had curative activity in this refractory model and is being investigated further.

A facile method for preparing substituted 1-aminoanthraquinones

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

Synthesis of Naphthindol-6(2H)-one Derivatives and Their Fluorescence Properties

Highly fluorescent 1-phenylnaphthindol-6(2H)-one (3b) and its 7-chloro and 7-amino derivatives were synthesized by reaction of 1-aminoanthraquinone with benzyl chloride in KOH-DMSO system, followed by treatment with aluminium chloride.The compound 3b was easily N-alkylated with various alkyl halides in KOH-DMSO system.The fluorescence quantum yields (Φf) of naphthindol-6(2H)-one derivatives 3 were high (0.5-0.7), except for 7-amino derivatives which did not fluoresce.The Φf of 7-chloro derivative (3d) was strongly dependent on solvent: 0.37 in ethanol; 0.02 in acetonitrile; 0 in benzene.The compounds 3 were demonstrated to be efficient laser dyes for 500-550 nm region.

Reactions of 1,5-Dichloroanthrachinone with Nucleophiles

Reactions of 1,5-dichloroanthraquinone (1) with various nucleophiles were examined to evaluate possibilities for selective substitution. 1-Amino-5-chloroanthraquinone was obtained from 1 by reaction with (a) sodium azide in dimethyl sulfoxide and (b ammonia in the presence of potassium fluoride, but 1 with potassium in ammonia gave 3-chlorobenzoic acid.Conditions were found for preferential substitution in reactions of 1 with (c) 4-toluidine, (d) hexamethylphosphoric triamide, and (e) N-methylformamide.Reagent e is preferred for making 1-chloro-5-(methylamino)anthraquinone, though this compound predominates in mixtures produced when d is used.Potassium hydroxide in 2-ethoxyethanol converts 1 to the corresponding mono- and diethers of 1,5-dihydroxyanthraquinone, while sodium hydrosulfide and 1 give bis(5-chloroanthraquinonyl)sulfide.

Process for the preparation of 1-acylamino-5(8)-chloroanthraquinones

The invention relates to a novel process for the preparation of 1-acylamino-5(8)-chloroanthraquinones, which are starting materials for the preparation of vat dyes. It is characterized in that 1,5(8)-dichloroanthraquinones is reacted with ammonia at temperatures of 190° to 240° C., the amino groups in the reaction mixture are completely acylated and the more sparingly soluble diacylaminoanthraquinone is separated off from the more readily soluble monoacylaminochloroanthraquinone. The new process yields reaction products which are purer and cheaper than those which are obtained by conventional methods. Moreover there are smaller waste water problems.

Process for the production of aminoanthraquinone compounds

The present invention concerns a novel process for the reduction of a nitro-anthraquinone compound of formula I: STR1 wherein M IS AN INTEGER 1, 2 OR 3, AND n is an integer 1, 2 or 3, The sum of m + n being 3, 4 or 5, and the rings A and B are either further substituted or unsubstituted, To the corresponding amino-anthraquinone compound which comprises reacting the compound of formula I with hydrazine in aqueous medium. The resulting amino-anthraquinone compounds are in general known and are useful intermediates in the production of anthraquinone dyestuffs.

Process for the manufacture of aminoanthraquinones

A process for the manufacture of 1-aminoanthraquinone and derivatives thereof and of diaminoanthraquinones by reduction of 1-nitroanthraquinone and the corresponding derivatives thereof and dinitroanthraquinone, which process comprises the use of a hydronaphthalene as reducing agent and solvent.