13076-29-4

Basic information

• Product Name: 1,4-DIMETHOXYANTHRACENE
• Synonyms: RARECHEM AQ BD AN08;1,4-dimethoxy-anthracen;1,4-Dimethoxyantracene;ANTHRACENE,1,4-DIMETHOXY-;1,4-DIMETHOXYANTRACENE 98%;1,4-Dimethoxyanthracene,98%;1,4-DIMETHOXYANTHRACENE
• CAS NO: 13076-29-4
• Molecular Formula: C₁₆H₁₄O₂
• Molecular Weight: 238.28
• Mol File: 13076-29-4.mol
• Article Data: 13

Chemical Properties

• Melting Point: 134.5-136.5 °C
• Boiling Point: 340.88°C (rough estimate)
• Flash Point: 178.9 °C
• Appearance: /
• Density: 1.0981 (rough estimate)
• Vapor Pressure: 8.51E-07mmHg at 25°C
• Refractive Index: 1.6290 (estimate)
• CAS DataBase Reference: 1,4-DIMETHOXYANTHRACENE(CAS DataBase Reference)
• NIST Chemistry Reference: 1,4-DIMETHOXYANTHRACENE(13076-29-4)
• EPA Substance Registry System: 1,4-DIMETHOXYANTHRACENE(13076-29-4)

Safety Data

• Safety Statements: 24/25
• Hazardous Substances Data: 13076-29-4(Hazardous Substances Data)

Usage

Chemical Properties

yellow crystalline powder

InChI:InChI=1/C16H14O2/c1-17-15-7-8-16(18-2)14-10-12-6-4-3-5-11(12)9-13(14)15/h3-10H,1-2H3

Upstream product

• 67-56-1 methanol 
• 7218-35-1 1,4-dihydroxyanthracene 
• 75847-32-4 1,4-dimethoxy-5,8,9,10-tetrahydro-anthracene 
• 74-88-4 methyl iodide 
• 81-64-1 1,4-dihydroxy-9,10-anthracenedione 
• 6119-74-0 1,4-dimethoxyanthraquinone 
• 587875-29-4 dimethoxytriptycene chloroquinone 
• 635-12-1 1,4-anthraquinone 
• 77-78-1 dimethyl sulfate 
• 50259-94-4 1,4-dimethoxy-anthrone 
• 74-96-4 ethyl bromide 
• 75829-98-0 1,4-dimethoxy-9,10-dihydro-9,10-anthracenediol 

Downstream Products

• 123676-17-5 12-(p-nitrobenzoyl)-1,3-dichloro-7,10-dimethoxy-11,12-dihydro-6,11<1',2'>-benzeno-6H-dibenz<1,4>oxazocine 
• 6119-74-0 1,4-dimethoxyanthraquinone 
• 253587-67-6 2,5,8-Trimethoxy-9,10-dihydro-9,10-[1,2]benzenoanthracene-1,4-dione 
• 69203-80-1 9,10-dihydro-9,10-[1,2]benzenoanthracene-1,4,5,8-tetraone 
• 69180-08-1 9,10-Dihydro-5,8-dimethoxy-9,10-<1',2'>benzenoanthracen-1,4-diol 
• 153480-34-3 ((C₄H₉)3P)2Ni(C₁₄H₈(OCH₃)2) 

Relevant articles and documents

Conversion of Alkoxy-9,10-anthraquinones to Alkoxyanthracenes

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Syntheses and bioactivities of substituted 9,10-dihydro-9,10-[1,2]benzenoanthracene-1,4,5,8-tetrones. Unusual reactivities with amines

A number of substituted 9,10-dihydro-9,10-[1,2]benzenoanthracene-1,4,5,8-tetrones have been synthesized and their anticancer and antimalarial activities evaluated. A one-pot synthesis of 2,5,8-trimethoxy-9,10-dihydro-9,10-[1,2]benzenoanthracene-1,4-dione (4) was achieved by heating a mixture of 1,4-dimethoxyanthracene, methoxyhydroquinone, silver oxide, and zinc iodide in toluene. Regioselective bromination of 4 and 2-methoxy-9,10-dihydro-9,10-[1,2]benzenoanthracene-1,4,5,8-tetrone (7) with N-bromosuccinimide provided 2-bromo-3,5,8-trimethoxy-9,10-dihydro-9,10-[1,2]-benzenoanthracene-1,4-dione and 2-bromo-3-methoxy-9,10-dihydro-9,10-[1,2]benzenoanthracene-1,4,5,8-tetrone (1), respectively. The reactions of 1 with aliphatic primary amines and secondary amines, respectively, produced different products, a result most likely attributed to the different basicities (or nucleophilicities) and steric effects of the two kinds of amines. The structure of the displacement product, 2-bromo-3- [2-(tert-butoxycarbonyl)ethylamino]-9,10-dihydro-9,10-[1,2] benzenoanthracene-1,4,5,8-tetrone, from the reaction of 1 with tert-butyl 3-aminopropanoate was unequivocally determined by a single-crystal X-ray analysis. IC50 values of triptycene bisquinones for the inhibition of L1210 leukemia cell viability are in the 0.11-0.27 μM range and for the inhibition of Plasmodium falciparum 3D7 are in the 4.7-8.0 μM range.

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.

The reaction of triptycene haloquinones with alkoxides. An unusual route to pentiptycene quinones

Triptycene haloquinones 3 react with sodium alkoxides in refluxing alcohol to afford, besides the expected substitution products, pentiptycene quinone 4. This approach to 4 is compared with a Diels-Alder strategy to the same compound.