2987-68-0

Basic information

• Product Name: Vat Red 42
• Synonyms: Vat Red 42;N,N'-(9,10-dihydro-9,10-dioxoanthracene-1,4-diyl)bisbenzamide;Vat red 42 (C.I. 61650);Algol Red 5G;C.I.61650;C.I.Vat Red 42;N-[4-(benzoylamino)-9,10-diketo-1-anthryl]benzamide;N-[4-(benzoylamino)-9,10-dioxoanthracen-1-yl]benzamide
• CAS NO: 2987-68-0
• Molecular Formula: C₂₈H₁₈N₂O₄
• Molecular Weight: 446.45352
• EINECS: 221-058-5
• Mol File: 2987-68-0.mol
• Article Data: 3

Chemical Properties

• Melting Point: 286.5 °C
• Boiling Point: 549.5ºC at 760 mmHg
• Flash Point: 156.3ºC
• Appearance: /
• Density: 1.409g/cm3
• Vapor Pressure: 4.01E-12mmHg at 25°C
• Refractive Index: 1.74
• PKA: 11.66±0.20(Predicted)
• CAS DataBase Reference: Vat Red 42(CAS DataBase Reference)
• NIST Chemistry Reference: Vat Red 42(2987-68-0)
• EPA Substance Registry System: Vat Red 42(2987-68-0)

Safety Data

• Hazardous Substances Data: 2987-68-0(Hazardous Substances Data)

Usage

Preparation

(a) 1,4-Diaminoanthraquinone and Benzoyl chloride condensation; (b) 1, 4 – Dichloroanthraquinone and Benzamide?(2 Moore) condensation.

Properties and Applications

yellow red. Dark red powder. Soluble in 1, 2, 3, 4 – Tetrahydronaphthalene and Xylene. In concentrated sulfuric acid for red, dilution after magenta precipitation; Alkaline reduction leuco for dark red light purple; Acid reduction leuco for yellow brown. This product is light brittle dye, with photosensitivity. Mainly used in color matching, dyeing cotton shoulds not be direct sunlight, or color shallow. Can be used for paper dyeing. Standard Ironing Fastness Chlorine bleach Light Fastness Mercerized Oxygen bleach Soaping Fading Stain ISO 3-4 5 7 5 4 3-4 4

Standard

Ironing Fastness

Fading

Stain

ISO

3-4

InChI:InChI=1/C28H18N2O4/c31-25-19-13-7-8-14-20(19)26(32)24-22(30-28(34)18-11-5-2-6-12-18)16-15-21(23(24)25)29-27(33)17-9-3-1-4-10-17/h1-16H,(H,29,33)(H,30,34)

Upstream product

• 128-95-0 1,4-diamino-9,10-anthraquinone 
• 65-85-0 benzoic acid 
• 5327-72-0 1,4-diamino-anthracene-9,10-diol 
• 98-88-4 benzoyl chloride 
• 98-95-3 nitrobenzene 
• 2475-44-7 disperse blue 14 
• 55-21-0 benzamide 
• 602-25-5 1,4-dichloroanthraquinone 

Downstream Products

• 23677-62-5 1,4-diamino-2-nitro-anthraquinone 
• 288614-81-3 1,4-bis-benzoylamino-2-nitro-anthraquinone 
• 103838-14-8 N,N'-(9,10-dihydroxy-anthracene-1,4-diyl)-bis-benzamide 
• 81-46-9 1-amino-4-benzamidoanthraquinone 

Relevant articles and documents

A Metal-Free, Nonconjugated Polymer for Solar Photocatalysis

Heterogeneous catalysts that can absorb light over the solar range are ideal for green photocatalysis. Recently, attention has been directed towards the generation of novel solar-light photocatalysts, in particular, metal-free polymers. Herein, it is demonstrated that a metal-free, nonconjugated, anthraquinone-based copolymer (poly[1,4-diamine-9,10-dioxoanthracene-alt-(benzene-1,4-dioic acid)] (COP)) with a strong absorption in the visible region is effective as a sunlight heterogeneous photocatalyst. As a proof of concept, it has been used to mineralize 2,5-dichlorophenol (2,5-DCP) in water under air and sunlight irradiation. The photocatalytic efficiency of COP compares well with that of TiO2-P25 when the reaction is carried out in a solar photoreactor in acid medium. Steady-state and time-resolved (absorption and emission) studies performed on COP suspended in 6:4 DMF/H2O have provided valuable information about the COP species generated under different pH conditions. Steady-state absorption and fluorescence data are consistent with the existence of a tautomeric equilibrium between the 9,10-keto and 1,10-iminoketo quinoid forms for the anthraquinone in the ground state. Moreover, in basic media, transient absorption measurements showed the presence of two bands ascribed to the tautomeric triplet excited states, whereas only one of the triplets was observed in acid medium. A mechanism for the photocatalyzed degradation of 2,5-DCP by COP is proposed on the basis of these observations.

Synthesis and structure-activity correlations of the cytotoxic bifunctional 1,4-diamidoanthraquinone derivatives

Anthraquinone-based compounds are attractive target for the design of new anticancer drugs. We have previously described a series of 1,5- and 1,4-difunctionalized anthraquinones, which exhibit different spectra of potency, together with human telomerase evaluation. The present study details the preparation of further, distinct series of regioisomeric difunctionalized amidoanthraquinone and examines their in vitro cytotoxicity in C6, Hepa G2, and 2.2.15 cell lines. Two structurally related compounds, mitoxantrone and adriamycin, were tested in parallel as positive controls. The structure-activity relationships indicated amido substitution may lead to a different mechanism of cytotoxicity. Compounds, which have -(CH2)n- side chains terminating in basic groups such as aminoalkyl-substituted, showed cytotoxic activity in several cell lines. The exact mode of intercalative binding may be dictated by the positional placement of substituent side chains. Implications for amidoanthraquinone cytotoxicity as potential anticancer agents are discussed. In addition, we further delineate the nature of the pharmacophore for this class of compounds, which provides a rational basis for the structure-activity relationships.