2381-23-9

Basic information

• Product Name: 9,10-DIOXO-9,10-DIHYDROANTHRACENE-2-SULFONYL CHLORIDE
• Synonyms: 9,10-DIOXO-9,10-DIHYDROANTHRACENE-2-SULFONYL CHLORIDE;9,10-Dioxo-9,10-dihydroanthracene-2-sulfonyl;9,10-diketoanthracene-2-sulfonyl chloride;9,10-dioxoanthracene-2-sulfonyl chloride
• CAS NO: 2381-23-9
• Molecular Formula: C₁₄H₇ClO₄S
• Molecular Weight: 306.72
• Mol File: 2381-23-9.mol

Chemical Properties

• Boiling Point: 514.3°Cat760mmHg
• Flash Point: 264.8°C
• Appearance: /
• Density: 1.567g/cm³
• Vapor Pressure: 1.09E-10mmHg at 25°C
• Refractive Index: 1.663
• CAS DataBase Reference: 9,10-DIOXO-9,10-DIHYDROANTHRACENE-2-SULFONYL CHLORIDE(CAS DataBase Reference)
• NIST Chemistry Reference: 9,10-DIOXO-9,10-DIHYDROANTHRACENE-2-SULFONYL CHLORIDE(2381-23-9)
• EPA Substance Registry System: 9,10-DIOXO-9,10-DIHYDROANTHRACENE-2-SULFONYL CHLORIDE(2381-23-9)

Safety Data

• Hazardous Substances Data: 2381-23-9(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
9,10-Dioxo-9,10-dihydroanthracene-2-sulfonyl chloride is used as a reactive intermediate in the preparation of various pharmaceuticals, agrochemicals, and dyes. Its reactivity allows for the formation of carbon-carbon and carbon-heteroatom bonds, making it a valuable component in the synthesis of complex organic molecules.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 9,10-Dioxo-9,10-dihydroanthracene-2-sulfonyl chloride is used as a key building block for the development of new drugs. Its ability to form various chemical bonds enables the creation of diverse molecular structures with potential therapeutic properties.
Used in Agrochemical Industry:
9,10-Dioxo-9,10-dihydroanthracene-2-sulfonyl chloride is also utilized in the agrochemical industry for the synthesis of new pesticides and other agricultural chemicals. Its reactivity and versatility contribute to the development of innovative and effective products for crop protection and management.
Used in Dye Production:
9,10-DIOXO-9,10-DIHYDROANTHRACENE-2-SULFONYL CHLORIDE is used as a starting material in the production of dyes, particularly those with specific color properties and stability. Its anthracene core provides a foundation for the development of dyes with unique characteristics.
Used in Fluorescent Dyes for Biological Imaging and Staining Applications:
9,10-Dioxo-9,10-dihydroanthracene-2-sulfonyl chloride is used in the production of fluorescent dyes for biological imaging and staining. Its anthracene moiety, when incorporated into dye molecules, can exhibit strong fluorescence, making it suitable for applications in microscopy, cell biology, and other areas of biological research.
Safety Precautions:
Due to the reactivity of 9,10-Dioxo-9,10-dihydroanthracene-2-sulfonyl chloride, it should be handled with care and used in a well-ventilated area by trained professionals to minimize potential hazards.

InChI:InChI=1/C14H7ClO4S/c15-20(18,19)8-5-6-11-12(7-8)14(17)10-4-2-1-3-9(10)13(11)16/h1-7H

Upstream product

• 7719-09-7 thionyl chloride 
• 84-48-0 2-sulfo-anthraquinone 
• 117-79-3 2-aminoanthraquinone 
• 17407-98-6 anthracene-2-sulfonyl chloride 
• 64-19-7 acetic acid 
• 84-65-1 9,10-phenanthrenequinone 
• 131-08-8 sodium anthraquinone-2-sulfonate 

Downstream Products

• 912278-57-0 C₄₀H₄₀N₂O₈S₂ 
• 15100-53-5 anthracene-2-sulfonic acid 
• 84-65-1 9,10-phenanthrenequinone 
• 13354-38-6 2-mercaptoanthraquinone 
• 131-09-9 2-chloroanthracene-9,10-dione 
• 158331-42-1 N-<4-butyl>-2-anthraquinonesulfonamide 
• 128164-54-5 6^A-(anthraquinone-2-sulfonyl)-β-cyclodextrin 
• 143657-40-3 2-(octadecylaminosulfonyl)anthraquinone 
• 108428-21-3 2-<(antraquinone-2-sulfonyl)oxy>benzaldehyde 
• 143657-41-4 2-(heptadecyloxysulfonyl)anthraquinone 
• 7475-47-0 9,10-dioxo-9,10-dihydro-anthracene-2-sulfonic acid anilide 
• 116436-32-9 9,10-dioxo-9,10-dihydro-anthracene-2-sulfonic acid amide 
• 13354-36-4 2,2'-disulfanediyl-di-anthraquinone 

Relevant articles and documents

Cell-Active Small Molecule Inhibitors of the DNA-Damage Repair Enzyme Poly(ADP-ribose) Glycohydrolase (PARG): Discovery and Optimization of Orally Bioavailable Quinazolinedione Sulfonamides

DNA damage repair enzymes are promising targets in the development of new therapeutic agents for a wide range of cancers and potentially other diseases. The enzyme poly(ADP-ribose) glycohydrolase (PARG) plays a pivotal role in the regulation of DNA repair mechanisms; however, the lack of potent drug-like inhibitors for use in cellular and in vivo models has limited the investigation of its potential as a novel therapeutic target. Using the crystal structure of human PARG in complex with the weakly active and cytotoxic anthraquinone 8a, novel quinazolinedione sulfonamides PARG inhibitors have been identified by means of structure-based virtual screening and library design. 1-Oxetan-3-ylmethyl derivatives 33d and 35d were selected for preliminary investigations in vivo. X-ray crystal structures help rationalize the observed structure-activity relationships of these novel inhibitors.

Design, synthesis and biological evaluation of new oligopyrrole carboxamides linked with tricyclic DNA-intercalators as potential DNA ligands or topoisomerase inhibitors

In the context of the design and synthesis of minor groove binding and intercalating DNA ligands some new oligopyrrole carboxamides were synthesized. These hybrid molecules (combilexins) possess a variable and conformatively flexible spacer at the N-terminal end. As intercalating tricyclic systems acridone, acridine, anthraquinones and in a special case iminostilbene terminate the N-terminal end of the pyrrole chain. The cytotoxicity was examined by the NCI antitumor screening, furthermore, biophysical as well as biochemical studies were performed in order to get some information about the DNA binding properties and topoisomerase inhibition effect of this new series of molecules.

Oxygen scavenging compositions

Epoxy anthraquinonesulfonamide compounds are disclosed having the Formula (I) wherein X1, X2, X3, X4, X5, X6, X7 and X8 are each independently selected from H, OH, NH2, C1-C40 alkyl, C1-C40 alkoxy, C1C40 alkanoyl, C1-C40 alkanol, C1-C40 alkylether, C1-C40 alkylthio, C1-C40 alkylamino, C1-C40 alkanolether, C1-C40 alkylaminoether, C1-C40 alkylsulfonyl, C1-C40 alkyl sulfonanmido, epoxy sulfonamido substituents, and sulfonate substituents, with the proviso that at least one of X1, X2, X3, X4, X5, X6, X7 and X8 is an epoxy sulfonamido substituent, and salts thereof. The compounds and reaction products thereof may be used in oxygen scavenging compositions. 1

Practical routes to the triarylsulfonyl chloride intermediate of a β3 adrenergic receptor agonist

A β3 adrenergic receptor agonist was prepared on a multi-kilogram scale in high yield and purity via a convergent synthesis. A key intermediate in this synthesis was an arylthiazolylbenzenesulfonyl chloride. The triaryl segment of this sulfonyl chloride was assembled at the thiazole ring via coupling of α-haloketone and thiobenzamide precursors (Hantzsch synthesis). Three strategies for introducing the para-sulfonyl chloride moiety were developed and evaluated. The sulfonation/chlorination and diazotization/chlorosulfonylation routes were found the most efficient.

New propylamine oligopyrrole carboxamides linked to a heterocyclic or anthraquinone system: Synthesis, DNA binding, topoisomerase I inhibition and cytotoxicity

Continuing our studies on combilexines, compounds consisting of a DNA intercalator linked to a minor groove ligand, new results are presented. The synthesis of a series of new propylamine oligopyrrole carboxamides closely related to netropsin and distamycin A, linked to a heterocyclic or anthraquinone system is reported. The cytotoxic activity in vitro, the DNA binding characteristics and the inhibition of the topoisomerase I of the compounds were studied in order to explain the biological mechanism of action of these new potential combilexines. Some of the synthesised compounds showed cytotoxic activity against human tumour cell lines, as well as DNA binding and topoisomerase I inhibiting properties.

Cationic anthraquinone derivatives as catalytic DNA photonucleases: Mechanisms for DNA damage and quinone recycling

Ammonium-substituted anthraquinone derivatives have been found to catalyze DNA cleavage upon irradiation with 350 nm light. Picosecond laser spectroscopy demonstrates that the excited quinones react with DNA by two separate oxidative pathways: electron transfer from a nearby base and hydrogen atom abstraction from the deoxyribose component of the nucleic acid backbone. Photo-oxidation of DNA by either pathway yields the one-electron-reduced form of the quinone as a byproduct. Back electron transfer from the reduced quinone to the oxidized base is the predominant decay path for the reduced quinone formed by the electron transfer pathway while that formed by hydrogen atom abstraction is converted back to the ground-state, fully oxidized form by reduction of molecular oxygen. The resulting superoxide anion is detected by its reduction of cytochrome c. Comparison of the spectroscopic data for two quinones with significant different cleavage efficiencies suggests that DNA cleavage by these quinone reagents results from the hydrogen-abstraction chemistry. The laser experiments further indicate that the quinone completes one cycle of excitation, oxidation of DNA, and reduction of oxygen within 10 μs, illustrating the potential utility of these agents for double-stranded cleavage of DNA.

Synthesis and photochemistry of some anthraquinone-substituted β-cyclodextrins

Anthraquinone-substituted β-cyclodextins (β-CD) 1-3 have been synthesized by reaction of the corresponding sulfonyl chlorides with β-CD. The anthraquinone-capped β-CD 3 is produced as a mixture of A,C and A,D isomers. Irradiation of 1-3 results in the formation of the corresponding hydroquinones and oxidation of the CD moiety. The main photoproduct from 2 after regeneration of the anthraquinone contains a C6 aldehyde in a hemiacetal or hydrate form. Molecular mechanics suggests that the position of the aldehyde is on the E-glucose ring and that the intramolar H-abstraction reaction shows some selectivity.

Studies on the Conformation of 5,15-Diarylporphyrins with (Arylsulfonyl)oxy Substituents

Dimeso-substituted octaalkylporphyrins, carrying an (arylsulfonyl)oxy group at the ortho position of the two (meso) phenyl groups, were synthesized from dipyrrolylmethanes and aldehydes.On account of a 1H NMR upfield shift in CDCl3 solution of 2-5 ppm for the aryl protons, a folded conformation is assumed in which the substituted aryl groups lie right above and below the porphyrin plane.In CDCl3/CF3COOH solution the upfield shifts are absent.The results of low-temperature 1H NMR measurements and ring-current calculations agreed with our assumptions.The sulfonyloxy group promotes folding of the molecule more than the ester, sulfonyl, sulfinyl, thio, or methylene group.In zinc porphyrins carrying anthraquinone substituents, intramolecular coordination was observed. ΔG, ΔH, and ΔS values for the various conformational equilibria were calculated from the NMR data.We suggest van der Waals interactions with a contribution of charge transfer as the driving force for the folding of the molecule.