2944-12-9

Usage

Type of compound

Synthetic dye

Common uses

Red pigment in industrial applications
Coloring of textiles
Coloring of plastics
Coloring of printing inks

Known for

High colorfastness
Does not fade easily when exposed to light, heat, or water

Additional uses

Reagent in organic synthesis
Sensitizing dye in the production of photosensitive materials

Safety precautions

Potential for skin and eye irritation
Potentially harmful if swallowed or inhaled
Handle with care

InChI:InChI=1/C26H18N2O2/c29-25-19-13-7-8-14-20(19)26(30)24-22(28-18-11-5-2-6-12-18)16-15-21(23(24)25)27-17-9-3-1-4-10-17/h1-16,27-28H

Upstream product

• 602-25-5 1,4-dichloroanthraquinone 
• 62-53-3 aniline 
• 17648-03-2 9,10-Dihydroxy-2,3-dihydro-anthracene-1,4-dione 
• 2944-28-7 1-(phenylamino)anthraquinone 
• 5327-72-0 1,4-diamino-anthracene-9,10-diol 
• 112996-71-1 1,4-bis(phenylamino)-2,3-dihydro-9,10-anthraquinone 
• 28736-42-7 1,4-difluoroanthracene-9,10-dione 
• 13460-50-9 metaboric acid 
• 64-19-7 acetic acid 
• 127-08-2 potassium acetate 
• 115374-43-1 1,4,10-trihydroxy-anthrone 
• 40498-13-3 2,3-dihydro-1,4-dihydroxyanthraquinone 
• 58497-41-9 2-benzoyl-3,6-dichloro-benzoic acid 
• 96701-06-3 9,10-dioxo-9,10-dihydroanthracene-1,4-diyl bis(4-methylbenzenesulfonate) 

Downstream Products

• 2944-13-0 1,4-di(4-nitroanilino)anthraquinone 
• 84-65-1 9,10-phenanthrenequinone 
• 76788-15-3 N-(9,10-Dioxo-4-phenylamino-9,10-dihydro-anthracen-1-yl)-N-phenyl-acetamide 
• 42985-05-7 1-(phenylamino)-4-(2-hydroxyethylamino)anthraquinone 

Relevant academic research and scientific papers

ANTHRAQUINONE QUENCHER DYES, THEIR METHODS OF PREPARATION AND USE

The invention provides novel anthraquinone compositions that are useful as broad-spectrum quenchers of fluorescence and provides methods for making and using them. The anthraquinone quenchers can be conjugated to a variety of biologically relevant compounds, including lipids, nucleic acids, polypeptides, and more specifically antigens, steroids, vitamins, drugs, haptens, metabolites, toxins, environmental pollutants, amino acids, peptides, proteins, nucleotides, oligonucleotides, polynucleotides, carbohydrates, and their analogs. The invention also provides kits comprising, in one or more containers, at least one anthraquinone quencher dye composition of the present invention, and instructions for using that composition.

Synthesis and Antitumor Evaluations of Symmetrically and Unsymmetrically Substituted 1,4-Bisanthracene-9,10-diones and 1,4-Bis-5,8-dihydroxyanthracene-9,10-diones

The ipso bis displacements of fluoride from 1,4-difluoroanthracene-9,10-dione (3) and 1,4-difluoro-5,8-dihydroxyanthracene-9,10-dione (4) by excess of a diamine (or a monoamine) in pyridine at room temperature lead to the symmetrically substituted 1,4-bis-substituted analogues 5 and 6, respectively.The ipso monodisplacements of fluoride from 3 and 4 can be accomplished by treatment with less than 1 molar equiv of a diamine (or a monoamine) to yield 7 and 8, respectively.Treatment of 7 or 8 with a different diamine leads to the unsymmetrically substituted1,4-bisanthracene-9,10-diones 9 and 10, respectively.Many of the synthetic unsymmetrical analogues have been evaluated for their antitumor activity against L1210 in vitro and in vivo.Cross resistance of analogue 10a with mitoxantrone (2) and doxorubicin was evaluated against MDR lines in vitro against human colon carcinoma LOVO and its subline resistant to DOXO (LOVO/DOXO).Potential mechanisms for the observed cytotoxicity are presented and discussed.

15N NMR STUDY OF AMINO-IMINO TAUTOMERISM IN DERIVATIVES OF 1,4-BIS(SUBSTITUTED AMINO)-9,10-ANTHRAQUINONES AND 1,4-BIS(SUBSTITUTED AMINO)-2,3-DIHYDRO-9,10-ANTHRAQUINONES

The 15N chemical shifts and 1J(15N,H) coupling constants of 1,4-bis(substituted amino)-9,10-anthraquinones and 1,4-bis(substituted amino)-2,3-dihydro-9,10-anthraquinones indicate that these derivatives exist as true aminoderivatives except for 1,4-bis(phenylamino)-2,3-dihydro-9,10-anthraquinone which forms a tautomeric mixture of the amino and imino forms in deuteriochloroform and hexadeuteriodimethyl sulphoxide.