117-11-3

Basic information

• Product Name: 1-Amino-5-chloroanthraquinone
• Synonyms: 1-amino-5-chloro-10-anthracenedione;1-Amino-5-chloroanthra-9,10-quinone;1-amino-5-chloro-anthraquinon;1-Chlor-5-aminoanthrachinon;5-Chloro-1-aminoanthraquinone;9,10-Anthracenedione, 1-amino-5-chloro-;Anthraquinone, 1-amino-5-chloro-;5-CHLORO-1-ANTHRAQUINONYLAMINE
• CAS NO: 117-11-3
• Molecular Formula: C₁₄H₈ClNO₂
• Molecular Weight: 257.67
• EINECS: 204-174-0
• Mol File: 117-11-3.mol
• Article Data: 7

Chemical Properties

• Melting Point: 204-210℃
• Boiling Point: 500.912 °C at 760 mmHg
• Flash Point: 256.743 °C
• Appearance: /
• Density: 1.2625 (rough estimate)
• Vapor Pressure: 3.64E-10mmHg at 25°C
• Refractive Index: 1.5270 (estimate)
• PKA: -1.48±0.20(Predicted)
• CAS DataBase Reference: 1-Amino-5-chloroanthraquinone(CAS DataBase Reference)
• NIST Chemistry Reference: 1-Amino-5-chloroanthraquinone(117-11-3)
• EPA Substance Registry System: 1-Amino-5-chloroanthraquinone(117-11-3)

Safety Data

• Statements: 36/37/38
• Safety Statements: 26-36/37/39
• RTECS: CB5435000
• TSCA: Yes
• Hazardous Substances Data: 117-11-3(Hazardous Substances Data)

Usage

General Description

1-Amino-5-chloroanthraquinone is a chemical compound with the molecular formula C14H8NO2Cl. It is a synthetic dye intermediate that is commonly used in the production of dyes, pigments, and other colorants. 1-Amino-5-chloroanthraquinone is a derivative of anthraquinone, which is a polycyclic aromatic hydrocarbon. It has a yellow-orange color and is soluble in organic solvents. 1-Amino-5-chloroanthraquinone is often used in textile dyeing and printing processes, as well as in the manufacturing of colored pencils and inks. This chemical is known to have moderate acute toxicity, so proper handling and storage measures should be taken to ensure safe usage and disposal.

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

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

Downstream Products

• 117-05-5 1-Chloro-5-benzoylaminoanthraquinone 
• 861791-83-5 2-(5-chloro-9,10-dioxo-9,10-dihydro-[1]anthrylamino)-benzaldehyde 
• 33175-77-8 1-amino-5-cyclohexylamino-anthraquinone 
• 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 
• 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 
• 129-43-1 1-hydroxyanthraquinone 
• 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 
• 128-95-0 1,4-diamino-9,10-anthraquinone 

Relevant articles and documents

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.

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.

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.