25060-18-8

Basic information

• Product Name: 1,4-DIHYDROXY-2,3-DIMETHYLANTHRAQUINONE
• Synonyms: 2,3-DIMETHYLQUINIZARIN;1,4-DIHYDROXY-2,3-DIMETHYLANTHRAQUINONE;1,4-Dihydroxy-2,3-dimethyl-9,10-anthraquinone;2,3-Dimethyl-1,4-dihydroxy-9,10-anthraquinone;Nsc321275
• CAS NO: 25060-18-8
• Molecular Formula: C₁₆H₁₂O₄
• Molecular Weight: 268.26
• Mol File: 25060-18-8.mol
• Article Data: 3

Chemical Properties

• Melting Point: 255-257 °C(lit.)
• Boiling Point: 526.9°Cat760mmHg
• Flash Point: 286.5°C
• Appearance: /
• Density: 1.423g/cm³
• Vapor Pressure: 1.02E-11mmHg at 25°C
• Refractive Index: 1.69
• CAS DataBase Reference: 1,4-DIHYDROXY-2,3-DIMETHYLANTHRAQUINONE(CAS DataBase Reference)
• NIST Chemistry Reference: 1,4-DIHYDROXY-2,3-DIMETHYLANTHRAQUINONE(25060-18-8)
• EPA Substance Registry System: 1,4-DIHYDROXY-2,3-DIMETHYLANTHRAQUINONE(25060-18-8)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• Hazardous Substances Data: 25060-18-8(Hazardous Substances Data)

Usage

General Description

1,4-Dihydroxy-2,3-dimethylanthraquinone is a chemical compound that belongs to the family of anthraquinones. It is a synthetic substance with a dark red color and is commonly used as a dye and pigment in various industrial applications. 1,4-DIHYDROXY-2,3-DIMETHYLANTHRAQUINONE is also known by the trade name "Alizarin Crimson" and is commonly used as a colorant in textiles, paints, and printing inks. In addition to its use as a dye, 1,4-dihydroxy-2,3-dimethylanthraquinone is also used in the production of certain pharmaceuticals and as a chemical intermediate in organic synthesis processes. However, it is important to handle this compound with care, as it can be harmful if ingested or inhaled and may cause skin and eye irritation.

InChI:InChI=1/C16H12O4/c1-7-8(2)14(18)12-11(13(7)17)15(19)9-5-3-4-6-10(9)16(12)20/h3-6,17-18H,1-2H3

Upstream product

• 85-44-9 phthalic anhydride 
• 608-43-5 2,3-dimethyl-1,4-dihydroxybenzene 

Downstream Products

• 75348-22-0 2,3-dimethyl-1,4-di-p-toluidino-anthraquinone 
• 128478-53-5 2-(4-Dicyanomethylene-2,3,5,6-tetrafluoro-cyclohexa-2,5-dienylidene)-malononitrile; compound with 3,4-dimethyl-1,2,5,6-tetratellura-cyclopenta[fg]aceanthrylene 
• 128478-52-4 2-(4-Dicyanomethylene-2,3,5,6-tetrafluoro-cyclohexa-2,5-dienylidene)-malononitrile; compound with 3,4-dimethyl-1,2,5,6-tetraselena-cyclopenta[fg]aceanthrylene 
• 128478-51-3 2-(4-Dicyanomethylene-2,3,5,6-tetrafluoro-cyclohexa-2,5-dienylidene)-malononitrile; compound with 3,4-dimethyl-1,2,5,6-tetrathia-cyclopenta[fg]aceanthrylene 
• 136560-05-9 2-(4-Dicyanomethylene-2,5-dimethoxy-cyclohexa-2,5-dienylidene)-malononitrile; compound with 3,4-dimethyl-1,2,5,6-tetratellura-cyclopenta[fg]aceanthrylene 
• 136560-04-8 2-(4-Dicyanomethylene-2,5-dimethoxy-cyclohexa-2,5-dienylidene)-malononitrile; compound with 3,4-dimethyl-1,2,5,6-tetraselena-cyclopenta[fg]aceanthrylene 
• 136560-03-7 2-(4-Dicyanomethylene-2,5-dimethoxy-cyclohexa-2,5-dienylidene)-malononitrile; compound with 3,4-dimethyl-1,2,5,6-tetrathia-cyclopenta[fg]aceanthrylene 
• 128517-29-3 3,4-Dimethyl-1,2,5,6-tetratellura-cyclopenta[fg]aceanthrylene; compound with 2-(4-dicyanomethylene-2,5-dimethyl-cyclohexa-2,5-dienylidene)-malononitrile 
• 128517-28-2 3,4-Dimethyl-1,2,5,6-tetraselena-cyclopenta[fg]aceanthrylene; compound with 2-(4-dicyanomethylene-2,5-dimethyl-cyclohexa-2,5-dienylidene)-malononitrile 
• 128517-27-1 3,4-Dimethyl-1,2,5,6-tetrathia-cyclopenta[fg]aceanthrylene; compound with 2-(4-dicyanomethylene-2,5-dimethyl-cyclohexa-2,5-dienylidene)-malononitrile 
• 128478-47-7 3,4-Dimethyl-1,2,5,6-tetratellura-cyclopenta[fg]aceanthrylene; compound with 2-(4-dicyanomethylene-cyclohexa-2,5-dienylidene)-malononitrile 
• 128478-46-6 3,4-Dimethyl-1,2,5,6-tetraselena-cyclopenta[fg]aceanthrylene; compound with 2-(4-dicyanomethylene-cyclohexa-2,5-dienylidene)-malononitrile 
• 128478-45-5 3,4-Dimethyl-1,2,5,6-tetrathia-cyclopenta[fg]aceanthrylene; compound with 2-(4-dicyanomethylene-cyclohexa-2,5-dienylidene)-malononitrile 
• 89024-03-3 (3aS,13aR)-5,12-Dihydroxy-2-phenyl-3a,4,13,13a-tetrahydro-2-aza-cyclopenta[b]naphthacene-1,3,6,11-tetraone 

Relevant articles and documents

Synthesis and Properties of Dimethyl and Tetramethyl Anthra-bisdichalcogenoles and Their Charge-Transfer Complexes

The dimethyl and tetramethyl derivatives of a series of anthrabisdithiole, diselenole, and ditellurole have been prepared as a new type of electron donor.The introduced methyl groups serve to enhance not only the donor strength, but also the solubility, enabling a ready formation of their charge-transfer complexes with various electron acceptors such as 7,7,8,8-tetracyanoquinodimethane (TCNQ), its 2,3,5,6-tetrafluoro derivative, 2,5-dimethyl derivative (DMTCNQ), 2,5-dimethoxy derivative (DMOTCNQ), 2,6-bis(dicyanomethylene)-2,6-dihydronaphthalene (TNAP), 3,3'-dichloro-5,5'-bis(dicyanomethylene)-Δ2,2'-bi(3-thiolene) (DCBT), and 3,3'-dibromo-5,5'-bis(dicyanomethylene)-Δ2,2'-bi(3-selenolene) (DBBS).Although the resulting complexes are mostly 1:1 stoichiometrical, the TCNQ complexes tend to favor a composition rich in acceptors; on the contrary, the DMTCNQ and DMOTCNQ complexes tend to favor a composition rich in donors.Their electrical conductivities range widely from 8 to 10-9 S cm-1, being apparently dependent on appropriate combinations of the donors and the acceptors.In general, the present donors have a tendency to form highly conductive complexes with TCNQ, TNAP, DCBT, and DBBS.These highly conductive complexes mostly show a broad electron absorption in the infrared region, being characteristic of a segregated stacked structure in a mixed valence state.On the other hand, the X-ray analysis of DMTCNQ complexes of 3,4-dimethyl, 8,9-dimethyl, and 3,4,8,9-tetramethylanthradiselenoles and 3,4,8,9-tetramethylanthradithiole have revealed that all of the crystal structures have mixed stack columns of donor-donor-acceptor type.Of them, the 3,4-dimethyl derivative complex shows an unusually high conductivity (0.53 S cm-1) for a mixed stacked structure, which is considered to be due to strong heteroatomic interactions of the intra- and inter-columns.

Simple o-Quinodimethane Route to (+/-)-4-Demethoxydaunomycinone

The anthracycline antibiotics daunorubicin and adriamycin are important clinically useful drugs in the treatment of a number of human cancers.The structurally simplified synthetic analogues 4-demethoxydaunorubicin and 4-demethoxyadriamycin show much clinical promise.The synthesis of the corresponding aglycon (+/-)-4-demethoxydaunomycinone from the inexpensive dye intermediate quinizarin, utilizing o-quinodimethane intermediates, is discussed.