131-09-9

Basic information

• Product Name: 2-Chloroanthraquinone
• Synonyms: anthraquinone,2-chloro-;β-chloroanthrapuinone ;Melting point standard 2-chloroanthraquinone;2-Chloroanthraqukinone;MELTING POINT STANDARD 2-CHLORO- &;2-Chloranthrachinon;2-Chloroanthraquinone,99%;2-Chloroanthraquinone,97%
• CAS NO: 131-09-9
• Molecular Formula: C₁₄H₇ClO₂
• Molecular Weight: 242.66
• EINECS: 205-010-0
• Product Categories: Intermediates of Dyes and Pigments;Organics;Electronic Chemicals;Anthraquinones;Chloroanthraquine, etc.;C13 to C14;Carbonyl Compounds;Ketones;API Intermediate
• Mol File: 131-09-9.mol
• Article Data: 9

Chemical Properties

• Melting Point: 209-211 °C(lit.)
• Boiling Point: 345.65°C (rough estimate)
• Flash Point: 179.7 °C
• Appearance: beige powder
• Density: 1.2377 (rough estimate)
• Vapor Pressure: 1.1E-07mmHg at 25°C
• Refractive Index: 1.5380 (estimate)
• Storage Temp.: Sealed in dry,Room Temperature
• Water Solubility: insoluble
• BRN: 2051842
• CAS DataBase Reference: 2-Chloroanthraquinone(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Chloroanthraquinone(131-09-9)
• EPA Substance Registry System: 2-Chloroanthraquinone(131-09-9)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38-43-36/37
• Safety Statements: 26-36-37/39-24
• WGK Germany: 1
• RTECS: CB6151000
• F: 10
• TSCA: Yes
• Hazardous Substances Data: 131-09-9(Hazardous Substances Data)

Usage

Description

2-Chloroanthraquinone is an organic compound with the chemical formula C14H7ClO2, characterized by its beige powder appearance. It is a derivative of anthraquinone, featuring a chlorine atom at the 2nd position, which imparts unique chemical properties to the molecule.

Uses

Used in Pharmaceutical Industry:
2-Chloroanthraquinone is used as an intermediate in the synthesis of various pharmaceutical compounds due to its unique chemical structure and reactivity. Its ability to form different types of chemical bonds makes it a valuable building block for the development of new drugs.
Used in Analytical Chemistry:
2-Chloroanthraquinone is used as a photo-reagent for the analysis of ginsenosides, a group of compounds found in ginseng that have various pharmacological properties. The photoreduction fluorescence (PRF) detection method employs 2-Chloroanthraquinone to analyze and quantify ginsenosides, providing a reliable and sensitive technique for their determination.

Synthesis Reference(s)

Tetrahedron Letters, 24, p. 5499, 1983 DOI: 10.1016/S0040-4039(00)94122-4

InChI:InChI=1/C14H9ClO2/c15-8-5-6-11-12(7-8)14(17)10-4-2-1-3-9(10)13(11)16/h1-7,9-10H

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Downstream Products

• 69470-36-6 2-chloro-9,10-diphenyl-9,10-dihydro-anthracene-9,10-diol 
• 95429-58-6 2-(2-nitro-anilino)-anthraquinone 
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• 605-32-3 2-hydroxy-9,10-anthraquinone 
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Relevant articles and documents

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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.

Process for preparation of 2-substituted 1,4-naphthoquinone

A process for preparation of a 2-substituted-1,4-naphthoquinone which comprises oxidizing a 2-substituted naphthalene to obtain reaction products comprising a 2-substituted-1,4-naphthoquinone and a 6-substituted-1,4-naphthoquinone; adding a diene compound to the reaction products and heating the mixture to form a Diels-Alder reaction adduct between the diene compound and the 6-substituted-1,4-naphthoquinone in the reaction products; and separating the 2-substituted-1,4-naphthoquinone from the adduct.