3571-23-1

Basic information

• Product Name: N-(9,10-dioxo-1-anthryl)benzamide
• Synonyms: N-(9,10-dioxo-1-anthryl)benzamide;1-(Benzoylamino)-9,10-anthraquinone;1-(Benzoylamino)anthracene-9,10-dione;Algol Yellow WG;C.I.60515;N-(9,10-Dihydro-9,10-dioxoanthracen-1-yl)benzamide
• CAS NO: 3571-23-1
• Molecular Formula: C₂₁H₁₃NO₃
• Molecular Weight: 327.33282
• EINECS: 222-674-7
• Mol File: 3571-23-1.mol
• Article Data: 7

Chemical Properties

• Boiling Point: 469.7°Cat760mmHg
• Flash Point: 164.6°C
• Appearance: /
• Density: 1.375g/cm³
• Vapor Pressure: 5.37E-09mmHg at 25°C
• Refractive Index: 1.712
• CAS DataBase Reference: N-(9,10-dioxo-1-anthryl)benzamide(CAS DataBase Reference)
• NIST Chemistry Reference: N-(9,10-dioxo-1-anthryl)benzamide(3571-23-1)
• EPA Substance Registry System: N-(9,10-dioxo-1-anthryl)benzamide(3571-23-1)

Safety Data

• Hazardous Substances Data: 3571-23-1(Hazardous Substances Data)

Usage

Description

N-(9,10-dioxo-1-anthryl)benzamide is a chemical compound with the molecular formula C20H13NO3. It is an anthracene derivative characterized by a benzene ring attached to an anthracene ring with an amide functional group. This unique structure endows it with distinctive chemical properties, making it a versatile molecule in various scientific and industrial applications.

Uses

Used in Fluorescent Dyes:
N-(9,10-dioxo-1-anthryl)benzamide is utilized as a fluorescent dye in biological and biochemical research. Its ability to absorb and emit light at specific wavelengths allows for its use in studying molecular interactions, cellular processes, and other biological phenomena.
Used in Organic Synthesis:
In the field of organic synthesis, N-(9,10-dioxo-1-anthryl)benzamide serves as a valuable chemical intermediate. Its unique structure and reactivity make it suitable for the synthesis of a wide range of organic compounds, including pharmaceuticals, agrochemicals, and other specialty chemicals.
Used in Pharmaceutical Production:
N-(9,10-dioxo-1-anthryl)benzamide has potential applications in the production of pharmaceuticals. Its unique chemical properties can be harnessed to develop new drugs or improve the synthesis of existing ones, contributing to advancements in medicine and healthcare.
Used in Agrochemical Production:
Similarly, in the agrochemical industry, N-(9,10-dioxo-1-anthryl)benzamide can be employed as a chemical intermediate for the synthesis of various agrochemicals, such as pesticides and herbicides. Its unique structure and reactivity can contribute to the development of more effective and environmentally friendly products.

InChI:InChI=1/C21H13NO3/c23-19-14-9-4-5-10-15(14)20(24)18-16(19)11-6-12-17(18)22-21(25)13-7-2-1-3-8-13/h1-12H,(H,22,25)

Upstream product

• 7446-70-0 aluminium trichloride 
• 55-21-0 benzamide 
• 82-45-1 1-amino-9,10-anthracenedione 
• 98-95-3 nitrobenzene 
• 7647-01-0 hydrogenchloride 
• 65-85-0 benzoic acid 
• 81-45-8 1-benzamido-4-chloroanthraquinone 
• 98-88-4 benzoyl chloride 
• 632-83-7 1-Bromoanthraquinone 
• 82-44-0 1-chloroanthracene-9,10-dione 

Downstream Products

• 77816-39-8 1-benzoylamino-4-(s-butylamino)anthraquinone 
• 131-92-0 4,9-bis-benzoylamino-16H-dinaphtho[2,3-a;2',3'-i]carbazole-5,10,15,17-tetraone 
• 128-89-2 4,5'-bis-benzoylamino-1,1'-imino-di-anthraquinone 
• 81-44-7 4-bromo-1-benzoylaminoanthraquinone 
• 77816-42-3 1-benzoylamino-4-benzylaminoanthraquinone 
• 82-38-2 1-(methylamino)anthraquinone 
• 77816-38-7 1-benzoylamino-4-butylaminoanthraquinone 
• 90466-61-8 1-benzoylamino-4-(t-butylamino)anthraquinone 
• 77816-41-2 1-benzoylamino-4-cyclohexylaminoanthraquinone 
• 134293-76-8 1-Benzoylamino-10-hydroxy-anthracen-9-ol anion 
• 77816-40-1 1-benzoylamino-4-(n-octylamino)anthraquinone 
• 81-45-8 1-benzamido-4-chloroanthraquinone 
• 95702-65-1 N-(9,10-dihydroxy-[1]anthryl)-benzamide 

Relevant articles and documents

PREPARATION METHOD OF ORIGINAL DYE OF VAT BROWN R

A preparation method of original dye of Vat Brown R comprises the following steps: a. after acylation of 1,5-diaminoanthraquinone, 1-amino-5-benzamidoanthraquinone was prepared by acidic hydrolysis; b. 1-benzamido-4-bromoanthraquinone was obtained from 1-aminoanthraquinone by acylation and bromination; c. a condensate of Vat Brown R was obtained by condensation reaction of 1-amino-5-benzamidoanthraquinone and 1-benzamido-4-bromoanthraquinone; d. the original dye of Vat Brown R was obtained from the condensate of Vat Brown R by ring closing reaction and oxidation reaction. The method omits one oxidation step, economizes significant amount of oxidizing agent, and reduces significant amount of waste water, so it is very beneficial to environment protection; and the method also exhibited the advantages of highly increasing product yield and reducing the costs of raw materials to an extent of more than 30%.

Novel anthraquinone derivatives with redox-active functional groups capable of producing free radicals by metabolism: Are free radicals essential for cytotoxicity?

The mode of action of antitumour anthraquinone derivatives (i.e. mitoxantrone) is not clearly established yet. It includes, among others, intercalation and binding to DNA, bioreduction and aerobic redox cycling. A series of anthraquinone derivatives, with potentially bioreducible groups sited in the side chain, have been synthesized and biologically evaluated. Their redox and cytotoxic activities were screened. Derivatives which bear a 2-(dimethylamino)ethylamino substituent, known to confer high DNA affinity, demonstrated cytotoxicity but not redox activity (beside the anthraquinone reduction). Conversely, derivatives which showed redox activity were not cytotoxic toward the P388 cell line. The results suggest that bioreduction is not the main mode of action in the cytotoxicity of anthraquinones.

CATALYSIS BY TETRABUTOXYTITANIUM IN REACTIONS OF SUBSTITUTED ANILINES WITH BENZOIC ACID

During the benzoylation of arylamines by benzoic acid in boiling o-xylene or trichlorobenzene, catalyzed by tetrabutoxytitanium, the N-arylbenzamides are formed with yields of up to 98percent.The reaction takes place with amino-, methoxy-, methyl-, halogeno-, and nitroanilines and 1-aminoanthraquinone. 4-Aminophenol does not react with benzoic acid.