2872-47-1

Basic information

• Product Name: 1-amino-4-chloroanthracene-9,10-dione
• Synonyms: 1-amino-4-chloroanthracene-9,10-dione;1-Amino-4-chloro-9,10-anthracenedione;1-AMINO-4-CHLORANTHRAQUINONE;1-amino-4-chloro-9,10-anthraquinone;1-azanyl-4-chloro-anthracene-9,10-dione
• CAS NO: 2872-47-1
• Molecular Formula: C₁₄H₈ClNO₂
• Molecular Weight: 257.67182
• Mol File: 2872-47-1.mol
• Article Data: 9

Chemical Properties

• Melting Point: 177-178 °C
• Boiling Point: 500.9°Cat760mmHg
• Flash Point: 256.7°C
• Appearance: /
• Density: 1.486g/cm³
• Vapor Pressure: 3.64E-10mmHg at 25°C
• Refractive Index: 1.711
• PKA: -1.03±0.20(Predicted)
• CAS DataBase Reference: 1-amino-4-chloroanthracene-9,10-dione(CAS DataBase Reference)
• NIST Chemistry Reference: 1-amino-4-chloroanthracene-9,10-dione(2872-47-1)
• EPA Substance Registry System: 1-amino-4-chloroanthracene-9,10-dione(2872-47-1)

Safety Data

• Hazardous Substances Data: 2872-47-1(Hazardous Substances Data)

Usage

Structure

Central anthracene ring with a chlorine atom at the 4th position, a dione functional group at the 9th and 10th positions, and an amino group at the 1st position.

Composition

Contains carbon, hydrogen, chlorine, nitrogen, and oxygen atoms.

Usage

Mainly used in organic synthesis and chemical research as a precursor for the synthesis of various organic compounds and pharmaceuticals.

Applications

Potential applications in dye stuff, pigments, and pharmaceuticals.

Precaution

Handle with care due to potential health and environmental hazards.

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

Upstream product

• 3274-19-9 1-(acetylamino)anthraquinone 
• 81-45-8 1-benzamido-4-chloroanthraquinone 
• 6337-82-2 1-Nitro-4-chloroanthraquinone 
• 82-45-1 1-amino-9,10-anthracenedione 
• 602-25-5 1,4-dichloroanthraquinone 
• 70-55-3 toluene-4-sulfonamide 
• 70730-89-1 6H-anthra<1,9-cd>isoxazol-6-one 
• 42013-62-7 1-azidoanthracene-9,10-dione 
• 131-09-9 2-chloroanthracene-9,10-dione 
• 98-82-8 Isopropylbenzene 
• 70730-92-6 5-chloro-6H-anthra[1,9-cd]isoxazol-6-one 
• 110-58-7 n-Pentylamine 
• 109-89-7 diethylamine 
• 126628-18-0 C₁₄H₇ClNO₂^(1-)*Na⁽¹⁺⁾ 

Downstream Products

• 54946-80-4 1-amino-4-o-anisidino-anthraquinone 
• 81-45-8 1-benzamido-4-chloroanthraquinone 
• 112128-36-6 N-(4-chloro-9,10-dioxo-9,10-dihydro-[1]anthryl)-N'-phenyl-urea 
• 23060-42-6 1-amino-4-p-anisidino-anthraquinone 
• 81-43-6 N-(4-amino-9,10-dioxo-9,10-dihydro-[1]anthryl)-anthranilic acid 
• 60878-31-1 2-(4-amino-9,10-dioxo-9,10-dihydro-[1]anthrylmercapto)-benzoic acid 
• 4395-65-7 oracet blue 2R 
• 476-42-6 2-fluoro-benzoic acid-(4-chloro-9,10-dioxo-9,10-dihydro-[1]anthrylamide) 
• 729580-53-4 2-(4-amino-9,10-dioxo-9,10-dihydro-[1]anthrylamino)-4-chloro-benzoic acid 
• 102241-47-4 1-amino-4-(4-methylsulfanyl-anilino)-anthraquinone 
• 54939-69-4 N-(4-amino-9,10-dioxo-9,10-dihydro-[1]anthryl)-benzenesulfonamide 
• 102546-50-9 1-chloro-4-[2-(toluene-4-sulfonyl)-ethylamino]-anthraquinone 
• 70730-92-6 5-chloro-6H-anthra[1,9-cd]isoxazol-6-one 
• 43096-07-7 3-Chloro-N-[4-(4-chloro-phenylamino)-9,10-dioxo-9,10-dihydro-anthracen-1-yl]-benzamide 

Relevant articles and documents

TRANSFORMATIONS OF ANTHRAISOXAZOL-6-ONES IN HYDROHALIC ACIDS

4-Halo-1-aminoanthraquinones are formed when anthraisoxazol-6-ones are refluxed in hydrohalic acids.The 3 position undergoes halogenation when 5-substituted isoxazoles are used.The process takes place via a one-proton mechanism with the participation of halide ion in the rate-determining step, possibly with the intermediate formation of N-haloaminoanthraquinones.

Synthesis of S,S-dialkyl-N-(9,10-dioxo-9,10-dihydroanthracen-1-yl) sulfoximides and specificities of their base-catalyzed intramolecular heterocyclizations into naphtho[1,2,3-cd]-indol-6(2H)-ones

Heating of 6H-anthra[1,9-cd][1,2]oxazol-6-ones with dialkyl sulfoxides in sulfolane gave S,S-dialkyl-N-(9,10-dioxo-9,10-dihydroanthracen-1-yl)sulfoximides which underwent cyclization to naphtho-[1,2,3-cd]indol-6(2H)-one derivatives on heating in boiling tetrahydrofuran in the presence of sodium methoxide. p-Toluenesulfinic acid was isolated as by-product in the cyclization of S-methyl-S-(4-methylphenyl)-N-(9,10-dioxo-9,10-dihydroanthracen-1-yl) sulfoximide. The heterocyclizations of S,S-dipropyl- and S,S-dibutyl-N-(9,10- dioxo-9,10-dihydroanthracen-1-yl)sulfoximides to 1-ethyl- and 1-propylnaphtho[1,2,3-cd]-indol-6(2H)-ones were accompanied by formation of the corresponding 1-[1-hydroxyethyl(propyl)]naphtho-[1,2,3-cd]indol-6(2H)-ones.

EQUILIBRIUM NH ACIDITY OF 4-SUBSTITUTED 1-AMINOANTHRAQUINONES IN DIMETHYL SULFOXIDE

The equilibrium acidity of 1-amino-4-R-anthraquinones (R = CH3O, H, Cl, Br, NO2) was determined by transmetallation in DMSO (the Na+ cation, 25 deg C).A linear correlation was established between the pK values of the 4-substituted 1-aminoanthraquinones and the ?p- constants of the substituents R.The conduction of the electronic effect of the substituents R is stronger in the aminoanthraquinones than in the anilines and is closer to the naphthylamines.A linear relation is observed between the conduction of the electronic effect of the substituent and the square of the coefficient in the HOMO for the carbon atom at the point of addiion of the substituent in the series of anions of NH acids of various structure types.The increase in the NH acidity with change in the structure type of the NH acid is not necessarily accompanied by a decrease in the conduction of the electronic effect of the substituents.

NUCLEOPHILIC SUBSTITUTION OF HYDROGEN IN AROMATIC SYSTEMS. II. MECHANISM OF AMINATION IN ANTHRAISOXAZOL-6-ONES

The nucleophilic substitution of the C5-H hydrogen atom in anthraisoxazol-6-ones by amines in acetonitrile in the absence of Cu2+, Ag+, Co2+, or Ni2+ cations takes place with the formation of strong hydrogen bond in the sixmembered chelate ring of the product from 1,4-addition of the amine to the isoxazolone at the C5 and =O atoms.The structure of the reaction product is determined by the character of the amine, and (with the absence of readily eliminated groups) substitution of C5-H is suppressed by the competing amination of C3-H and reduction of the heterocycle.The substitution of C5-Hlg by amines under analogous conditions leads to trivial reaction products.In nitromethane C3-H or C3-Hlg is mainly substituted, and C5-H or C5-Hlg is partly substituted, leading to products with trivial structures.In the presence of Cu2+, Ag+, Co2+, Ni2+ cations in acetonitrile only C3-H or C3-Hlg is substituted through the formation of mixed complex of amine and isoxazolone on the cation.