6119-74-0

Basic information

• Product Name: 1,4-DIMETHOXYANTHRAQUINONE
• Synonyms: 1,4-DIMETHOXYANTHRAQUINONE;1,4-Dimethoxy-9,10-anthracenedione;1,4-Dimethoxy-9,10-anthraquinone;Quinizarin dimethyl ether;9,10-Anthracenedione, 1,4-dimethoxy-;Anthraquinone, 1,4-dimethoxy-;Nsc103059;1,4-dimethoxyanthracene-9,10-dione
• CAS NO: 6119-74-0
• Molecular Formula: C₁₆H₁₂O₄
• Molecular Weight: 268.26408
• Mol File: 6119-74-0.mol
• Article Data: 30

Chemical Properties

• Boiling Point: 462.1°C at 760 mmHg
• Flash Point: 207.9°C
• Appearance: /
• Density: 1.295g/cm³
• Vapor Pressure: 1.02E-08mmHg at 25°C
• Refractive Index: 1.612
• CAS DataBase Reference: 1,4-DIMETHOXYANTHRAQUINONE(CAS DataBase Reference)
• NIST Chemistry Reference: 1,4-DIMETHOXYANTHRAQUINONE(6119-74-0)
• EPA Substance Registry System: 1,4-DIMETHOXYANTHRAQUINONE(6119-74-0)

Safety Data

• Hazardous Substances Data: 6119-74-0(Hazardous Substances Data)

Usage

Chemical Family

Anthraquinones

Physical State

Crystalline solid

Color

Reddish-brown

Uses

a. Dye intermediate
b. Production of vat dyes

Properties

a. Excellent light and weather resistance
b. Anti-fungal
c. Anti-bacterial

Applications

a. Coloring of materials (textiles, plastics, coatings)
b. Organic electronics (building block for synthesis of functional materials)
c. Organic semiconductors
d. Dyes for solar cells
e. Development of new pharmaceuticals and agrochemicals

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

Upstream product

• 25022-95-1 1-chloro-4-methoxy-anthraquinone 
• 124-41-4 sodium methylate 
• 71192-84-2 1,4-Dimethoxyspirodioxolan>-10-one 
• 13076-29-4 1,4-dimethoxyanthracene 
• 25245-34-5 1-bromo-2,5-dimethoxybenzene 
• 27613-27-0 3-oxo-1,3-dihydroisobenzofuran-1-carbonitrile 
• 78048-05-2 9a-Chloro-1,1,4-trimethoxy-1,4,4a,9a-tetrahydro-anthraquinone 
• 78048-05-2 (4α,4aβ,9aβ)-9a-chloro-1,1,4-trimethoxy-1,4,4a,9a-tetrahydroanthraquinone 
• 81-64-1 1,4-dihydroxy-9,10-anthracenedione 
• 74-88-4 methyl iodide 
• 60-29-7 diethyl ether 
• 71-43-2 benzene 
• 77-78-1 dimethyl sulfate 
• 6383-64-8 ethylene glycol monoketal of benzocyclobutenedione 

Downstream Products

• 128-80-3 D and C green 6 
• 30605-93-7 1,4-dimethoxy-9,10-diphenyl-9,10-dihydro-anthracene-9,10-diol 
• 29420-31-3 Phenyl-10-hydroxy-10-dimethoxy-1,4-anthron 
• 30605-89-1 Di-(p-vinylphenyl)-9,10-dihydroxy-9,10-dihydro-9,10-dimethoxy-1,4-anthracen 
• 81-64-1 1,4-dihydroxy-9,10-anthracenedione 
• 69203-80-1 9,10-dihydro-9,10-[1,2]benzenoanthracene-1,4,5,8-tetraone 
• 70866-25-0 1,4-bis(4-methylphenyl)-9,10-anthracenedione 
• 17055-09-3 4,7-dimethoxy-benzo[1,3]dioxole-5-carbaldehyde 
• 85-44-9 phthalic anhydride 
• 17354-14-2 solvent blue 35 
• 82874-66-6 1-(Butylamino)-4-methoxyanthracene-9,10-dione 
• 1386983-33-0 1,4-di(4-methylphenyl)-5,8-di(2-(2-methylphenyl)ethyl)-9,10-anthracenedione 
• 1386983-31-8 1,4-di(4-methylphenyl)-5,8-bis(2-(trimethylsilyl)ethyl)-9,10-anthracenedione 

Relevant articles and documents

N,N'-Diphenyl-1,4(5)-dimethoxyanthraquinone Diimines: "Butterfly" Inversion of Anthraquinone Diimines

Model compounds for polyaromatic quinone imines were synthesized and characterized by variable-temperature 1H NMR spectroscopy and X-ray single crystal structure determination.N,N'-Diphenyl-1,4(5)-dimethoxyanthraquinone 9,10-diimines were synthesized by condensing 2 equiv of aniline with 1,5-dimethoxyanthraquinone (15DMAQ) and 1,4-dimethoxyanthraquinone (14DMAQ), respectively, in the presence of titanium tetrachloride and 1,4-diazabicyclooctane (DABCO).The X-ray single crystal structure determination of the diimine of 15DMAQ is reported.The condensation of aniline with anthraquinones results in a buckling of the anthraquinone ring system, giving it a "butterfly" conformation while the diimine of 15DMAQ has an anti configuration with the N-phenyl rings lying above the methoxy substituents.The diimine of 14DMAQ has a syn configuration, again with these N-phenyl rings lying above the methoxy substituents.The symmetrical structural butterfly conformations of the diimines allowed for the observation of a dynamic butterfly inversion by variable-temperature 1H NMR spectroscopy.The energy barriers for the butterfly inversion of N-phenyl 15DMAQ and 14DMAQ diimines are 9.5 kcal/mol.The implications of the crystal structure and molecular dynamics for the polymeric structures are discussed.

1,4-Dipole-Metalated Quinone Strategy to (+/-)-4-Demethoxydaunomycinone and (+/-)-Daunomycine. Annelation of Benzocyclobutenedione Monoketals with Lithioquinone Bisketals

A strategy for total synthesis of anthracyclinones is outlined in which a benzocyclobutenedione monoketal, serving as a 1,4-dipole equivalent, is reacted with a lithiated quinone bisketal, serving as a metalated quinone equivalent, to afford in one step a fully functionalized tetracyclic ring system.A convenient synthesis of the AB-ring system with the eventual C7 and C9 oxygen functions of the anthracyclinone present has been developed.In addition, a trimethylsilyl-mediated benzylic bromination serves as one of the key steps in a novel methylene-to-carbonyl transformation, resulting in a regiospecific route to benzocyclobutenedione monoketals.The potential general synthetic utility arising from trimethylsilyl-stabilized radical intermediates is noted.The chemistry described above resulted in a convergent, regiospecific route to (+/-)-4-demethoxydaunomycinone and (+/-)-daunomycinone

Clip[5]arenes: A new family of molecular clips

Here we report the design and syntheses of two new triptycene-based rigid acyclic C-shaped hosts, clip[5]arenes C[5]OH and C[5]ME, and the strong host–guest complexation between C[5]OH and an electron-poor bipyridinium salt, paraquat G. The Ka value for the host–guest complex C[5]OH ? G was calculated to be (1.09 ± 0.36) × 105 M?1 in acetone by using a non-linear curve-fitting method based on the UV–vis absorption titration experiments. Furthermore, based on this new host–guest recognition motif, a novel pseudopolyrotaxane-like supramolecular structure was constructed with C[5]OH threaded on polyviologen polymer VP-10.

Access to 1,2,3,4-Tetraoxygenated Benzenes via a Double Baeyer-Villiger Reaction of Quinizarin Dimethyl Ether: Application to the Synthesis of Bioactive Natural Products from Antrodia camphorata

The first systematic investigation into the Baeyer-Villiger reaction of an anthraquinone is presented. The double Baeyer-Villiger reaction of quinizarin dimethyl ether is viable, directly providing the dibenzo[b,f][1,4]-dioxocin-6,11-dione ring-system, which is otherwise difficult to prepare. This methodology provides rapid access to 1,2,3,4-tetraoxygenated benzenes, and has been exploited by application to the total synthesis of a natural occurring benzodioxole and its biphenyl dimer, which both display noteworthy biological activity. Interestingly, the axially chiral biphenyl was found to be configurationally stable, but the resolved enantiomers exhibit no optical activity at the αD-line.