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

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

Downstream Products

• 82-24-6 1-aminoanthraquinone-2-carboxylic acid 
• 82-23-5 1-chloro-9,10-dioxo-9,10-dihydro-anthracene-2-carboxylic acid 
• 602-10-8 1-nitro-9,10-dioxo-9,10-dihydroanthracene-2-carbonyl chloride 
• 82-45-1 1-amino-9,10-anthracenedione 
• 3737-76-6 Vat Red KKh 
• 95310-34-2 3-methoxycarbonylanthra<1,9-cd>-6-isoxazolone 
• 80685-64-9 1-nitro-9,10-dioxo-9,10-dihydroanthracene-2-carboxanilide 
• 100440-89-9 N-benzyl-1-nitro-9,10-dioxo-9,10-dihydroanthracene-2-carboxamide 
• 442631-97-2 2-phenyl-2,3,6,11-tetrahydroanthra[2,1-d]isothiazole-3,6,11-trione 
• 430433-65-1 1-methylthio-9,10-dioxo-9,10-dihydroanthracene-2-carboxanilide 
• 430433-68-4 1-ethylthio-9,10-dioxo-9,10-dihydroanthracene-2-carboxanilide 
• 430433-66-2 N-benzyl-1-methylthio-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 
• 430433-69-5 N-benzyl-1-ethylthio-9,10-dioxo-9,10-dihydroanthracene-2-carboxamide 

Relevant articles and documents

Novel anthraquinone compounds inhibit colon cancer cell proliferation via the reactive oxygen species/JNK pathway

A series of amide anthraquinone derivatives, an important component of some traditional Chinese medicines, were structurally modified and the resulting antitumor activities were evaluated. The compounds showed potent anti-proliferative activities against eight human cancer cell lines, with no noticeable cytotoxicity towards normal cells. Among the candidate compounds, 1-nitro-2-acyl anthraquinone-leucine (8a) showed the greatest inhibition of HCT116 cell activity with an IC50 of 17.80 μg/mL. In addition, a correlation model was established in a three-dimensional quantitative structure-activity relationship (3D-QSAR) study using Comparative Molecular Field Analysis (CoMFA) and comparative molecular similarity index analysis (CoMSIA). Moreover, compound 8a effectively killed tumor cells by reactive oxygen species (ROS)-JNK activation, causing an increase in ROS levels, JNK phosphorylation, and mitochondrial stress. Cytochrome c was then released into cytoplasm, which, in turn activated the cysteine protease pathway and ultimately induced tumor cell apoptosis, suggesting a potential use of this compound for colon cancer treatment.

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.