128-67-6

Basic information

• Product Name: kyselina1-nitroanthrachinon-2-karboxylova
• Synonyms: 1-nitro-10-anthraquinone-2-carboxylicacid;1-nitro-2-anthraquinonecarboxylicacid;1-nitro-2-carboxyanthraquinone;9,10-dihydro-1-nitro-9,10-dioxo-2-anthroicaci;9,10-dihydro-1-nitro-9,10-dioxo-2-anthroicacid;kyselina1-nitroanthrachinon-2-karboxylova;9,10-dihydro-1-nitro-9,10-dioxoanthracene-2-carboxylic acid;9,10-Dihydro-1-Nitro-9,10-Dioxoanthralene-2-Carboxylic Acid
• CAS NO: 128-67-6
• Molecular Formula: C₁₅H₇NO₆
• Molecular Weight: 297.21918
• EINECS: 204-904-8
• Product Categories: Intermediates of Dyes and Pigments
• Mol File: 128-67-6.mol
• Article Data: 6

Chemical Properties

• Boiling Point: 438.74°C (rough estimate)
• Flash Point: 252.3°C
• Appearance: /
• Density: 1.3788 (rough estimate)
• Vapor Pressure: 5.22E-15mmHg at 25°C
• Refractive Index: 1.6231 (estimate)
• CAS DataBase Reference: kyselina1-nitroanthrachinon-2-karboxylova(CAS DataBase Reference)
• NIST Chemistry Reference: kyselina1-nitroanthrachinon-2-karboxylova(128-67-6)
• EPA Substance Registry System: kyselina1-nitroanthrachinon-2-karboxylova(128-67-6)

Safety Data

• Hazardous Substances Data: 128-67-6(Hazardous Substances Data)

Usage

General Description

Kyselina 1-nitroanthrachinon-2-karboxylova, also known as 1-nitroanthraquinone-2-carboxylic acid, is a chemical compound with the molecular formula C15H8N2O6. It is a derivative of anthraquinone and is commonly used as a dye intermediate in the production of colored pigments and as a precursor in the synthesis of other organic compounds. The compound has a yellow to orange color and is soluble in organic solvents but sparingly soluble in water. It is primarily used in the textile industry for dyeing and printing processes. Additionally, it has potential applications in the pharmaceutical and chemical industries for the production of various organic compounds.

InChI:InChI=1/C15H7NO6/c17-13-7-3-1-2-4-8(7)14(18)11-9(13)5-6-10(15(19)20)12(11)16(21)22/h1-6H,(H,19,20)/p-1

Upstream product

• 7664-93-9 sulfuric acid 
• 129-15-7 1-nitro-2-methylanthraquinone 
• 85-44-9 phthalic anhydride 
• 108-88-3 toluene 
• 84-54-8 2-methylanthracene-9,10-dione 
• 74214-86-1 2-bromomethyl-1-nitro-anthraquinone 
• 7697-37-2 nitric acid 
• 80685-73-0 ethyl 1-nitroanthraquinone-2-carboxylate 
• 105-56-6 ethyl 2-cyanoacetate 

Downstream Products

• 82-24-6 1-aminoanthraquinone-2-carboxylic acid 
• 82-45-1 1-amino-9,10-anthracenedione 
• 875838-32-7 1-(N-acetyl-p-toluidino)-9,10-dioxo-9,10-dihydro-anthracene-2-carboxylic acid 
• 872293-91-9 2,7-dioxo-3-p-tolyl-2,7-dihydro-3H-naphtho[1,2,3-de]quinoline-4-carboxylic acid 
• 7400-93-3 1-hydroxy-9,10-dioxoanthracene-2-carboxylic acid 
• 430433-69-5 N-benzyl-1-ethylthio-9,10-dioxo-9,10-dihydroanthracene-2-carboxamide 
• 610788-23-3 2-benzyl-2,3,6,11-tetrahydroanthra[2,1-d]isothiazole-3,6,11-trione 
• 430433-66-2 N-benzyl-1-methylthio-9,10-dioxo-9,10-dihydroanthracene-2-carboxamide 
• 430433-68-4 1-ethylthio-9,10-dioxo-9,10-dihydroanthracene-2-carboxanilide 
• 430433-65-1 1-methylthio-9,10-dioxo-9,10-dihydroanthracene-2-carboxanilide 
• 442631-97-2 2-phenyl-2,3,6,11-tetrahydroanthra[2,1-d]isothiazole-3,6,11-trione 
• 100440-89-9 N-benzyl-1-nitro-9,10-dioxo-9,10-dihydroanthracene-2-carboxamide 
• 80685-64-9 1-nitro-9,10-dioxo-9,10-dihydroanthracene-2-carboxanilide 
• 95310-34-2 3-methoxycarbonylanthra<1,9-cd>-6-isoxazolone 

Relevant articles and documents

Design, Synthesis, Molecular Docking, and Biological Evaluation of New Emodin Anthraquinone Derivatives as Potential Antitumor Substances

The emodin anthraquinone derivatives are generally used in traditional Chinese medicine due to their various pharmacological activities. In the present study, a series of emodin anthraquinone derivatives have been designed and synthesized, among which 1,3-dihydroxy-6,8-dimethoxyanthracene-9,10-dione is a natural compound that has been synthesized for the very first time, and 1,3-dimethoxy-5,8-dimethylanthracene-9,10-dione is a compound that has never been reported earlier. Interestingly, while total seven of these compounds showed neuraminidase inhibitory activity in influenza virus with inhibition rate more than 50 %, specific four compounds exhibited significant inhibition of tumor cell proliferation. The further results demonstrate that 1,3-dimethoxy-5,8-dimethylanthracene-9,10-dione showed the best anticancer activity among all the synthesized compounds by inducing highest apoptosis rate to HCT116 cancer cells and arresting their G0/G1 cell cycle phase, through elevation of intracellular level of reactive oxygen species (ROS). Moreover, the binding of 1,3-dimethoxy-5,8-dimethylanthracene-9,10-dione with BSA protein has thoroughly been investigated. Altogether, this study suggests the neuraminidase inhibitory activity and antitumor potential of the new emodin anthraquinone derivatives.

Preparation of 1-nitroanthraquinone-2-carboxylic acids

1-Nitroanthraquinone-2-carboxylic acids of the general formula I STR1 where X is hydrogen, chlorine or bromine, are prepared by oxidizing a 1-nitro-2-methylanthraquinone of the general formula II STR2 with nitric acid in an organic reaction medium.

Preparation of 1-nitroanthraquinone-2-carboxylic acid

1-Nitroanthraquinone-2-carboxylic acid of the formula I STR1 is prepared by treating novel 2-substituted 1-nitroanthraquinones of the general formula II STR2 where R is --CH=CH--R1 or --CH2 --CHO, where R1 is C1 -C5 -dialkylamino or a cyclic 5- or 6-membered amine which may contain further hetero atoms, with oxidizing agents free of heavy metal.