82-39-3

Basic information

• Product Name: 1-methoxyanthraquinone
• Synonyms: 1-methoxyanthraquinone;1-methoxyanthracene-9,10-dione;1-Methoxyquinone;1-methoxy-9,10-anthraquinone
• CAS NO: 82-39-3
• Molecular Formula: C₁₅H₁₀O₃
• Molecular Weight: 139.12868
• EINECS: 201-418-8
• Mol File: 82-39-3.mol

Chemical Properties

• Boiling Point: 340.83°C (rough estimate)
• Flash Point: 194.1°C
• Appearance: /
• Density: 1.2068 (rough estimate)
• Vapor Pressure: 1.41E-07mmHg at 25°C
• Refractive Index: 1.6000 (estimate)
• CAS DataBase Reference: 1-methoxyanthraquinone(CAS DataBase Reference)
• NIST Chemistry Reference: 1-methoxyanthraquinone(82-39-3)
• EPA Substance Registry System: 1-methoxyanthraquinone(82-39-3)

Safety Data

• Hazardous Substances Data: 82-39-3(Hazardous Substances Data)

Usage

Uses

Used in Catalyst Industry:
1-Methoxyanthraquinone is used as a catalyst to accelerate chemical reactions, enhancing the efficiency and speed of various industrial processes.
Used in Dye Production:
1-Methoxyanthraquinone is utilized in the production of dyes, contributing to the vibrant coloration of textiles, plastics, and other materials.
Used in Solar Cell Manufacturing:
As a photosensitizer, 1-Methoxyanthraquinone plays a crucial role in the production of solar cells, where it helps in capturing and converting sunlight into electricity.
Used in Pharmaceutical Manufacturing:
1-Methoxyanthraquinone is employed in the manufacturing of pharmaceuticals, potentially contributing to the development of new drugs and therapies.
Used in Organic Light-Emitting Diode (OLED) Technology:
1-Methoxyanthraquinone has been studied for its potential use in OLEDs, where it could improve the efficiency and performance of these light-emitting devices.
Used in Lithium-Ion Battery Development:
1-Methoxyanthraquinone is also considered as a component in the development of lithium-ion batteries, where it may enhance energy storage capacity and performance.

InChI:InChI=1/C15H10O3/c1-18-12-8-4-7-11-13(12)15(17)10-6-3-2-5-9(10)14(11)16/h2-8H,1H3

Upstream product

• 67-56-1 methanol 
• 82-34-8 1-nitroanthraquinone 
• 82-44-0 1-chloroanthracene-9,10-dione 
• 17613-65-9 1-phenoxy-anthraquinone 
• 30845-78-4 potassium 9,10-dihydro-9,10-dioxoanthracene-1-sulfonate 
• 77900-35-7 1-methoxy-9(10H)-anthracenone 
• 108-86-1 bromobenzene 
• 4792-33-0 4-methoxyphthalide 
• 2398-37-0 3-methoxyphenyl bromide 
• 27613-27-0 3-oxo-1,3-dihydroisobenzofuran-1-carbonitrile 
• 578-57-4 2-bromoanisole 
• 106500-34-9 1-ethoxy-3-(trimethylsilyl)isobenzofuran 
• 129237-15-6 1-(N-Benzoyl-N-benzylamino)-5-methoxy-1,4,4a,9a-tetrahydro-9,10-anthraquinone 
• 100-66-3 methoxybenzene 

Downstream Products

• 82-38-2 1-(methylamino)anthraquinone 
• 80034-12-4 1-methoxy-9,10-bis(phenylethynyl)-9,10-dihydroanthracene-9,10-diol 
• 655-04-9 1,2-anthraquinone 
• 129-43-1 1-hydroxyanthraquinone 
• 32287-29-9 1-methoxy-9,10-diphenyl-9,10-dihydro-9,10-epidioxido-anthracene 
• 13076-30-7 1-methoxy-9,10-diphenylanthracene 
• 128-80-3 D and C green 6 
• 116-85-8 4-hydroxy-1-aminoanthraquinone 
• 51580-22-4 1-methoxy-9,10-bis(phenylethynyl)anthracene 
• 77953-83-4 4-methoxy-10-(3,5-dimethylbenzyl)anthrone 
• 54458-84-3 1-methoxyanthracene 
• 7470-93-1 4-methoxy-anthrone 
• 6003-12-9 alizarin dimethyl ether 
• 1715-81-7 1-hydroxy-9(10H)-anthracenone 

Relevant articles and documents

Electrochemical Switching of Lariat Ethers: Enhanced Cation Binding by One- and Two-electron Reduction of an Anthraquinone Sidearm

The first example of cation binding enhancement by electrochemical switching in a lariat ether, accomplished by one- or two-electron reduction of a quinone sidearm, is presented.

Regioselectivity of Alkoxyisobenzofuran-Aryne Cycloadditions

The cycloaddition reactions of some unsymmetrical arynes with 1-ethoxy-3-(trimethylsilyl)isobenzofuran and a naphthofuran analogue were examined for prospective regioselectivity.The arynes, generated by lithium tetramethylpiperidide induced dehydrohalogenation of the appropriate haloaromatics, were 3-bromo, 3-chloro, 3-methoxy, and 3-methylbenzyne, 3,4-pyridyne, and 1,2-naphthalyne.Regioselectivities ranged from nil (50/50 isomer ratio with 3,4-pyridyne) to modest (ca. 80/20).The products are bridgehead trimethylsilylated ketals, which undergo a novel acid-catalyzed rearrangement to 9-alkoxy-10-anthracenes.These position-differentiated anthracenediol analogues are thought to be formed by ring opening, followed by Brook rearrangement.Isomeric ketal pairs were found to react at different rates, and this selective decomposition was used to isolate one of the cycloadduct isomers from the reaction of 3-bromobenzyne.Lithium-bromine exchange followed by methylation was used to determine its structure, and this information in turn was used to clarify the mechanism of the acid-catalyzed reaction.

Characterization of TnmH as an O-Methyltransferase Revealing Insights into Tiancimycin Biosynthesis and Enabling a Biocatalytic Strategy to Prepare Antibody-Tiancimycin Conjugates

The enediynes are among the most cytotoxic molecules known, and their use as anticancer drugs has been successfully demonstrated by targeted delivery. Clinical advancement of the anthraquinone-fused enediynes has been hindered by their low titers and lack of functional groups to enable the preparation of antibody-drug conjugates (ADCs). Here we report biochemical and structural characterization of TnmH from the tiancimycin (TNM) biosynthetic pathway, revealing that (i) TnmH catalyzes regiospecific methylation at the C-7 hydroxyl group, (ii) TnmH exhibits broad substrate promiscuity toward hydroxyanthraquinones and S-alkylated SAM analogues and catalyzes efficient installation of reactive alkyl handles, (iii) the X-ray crystal structure of TnmH provides the molecular basis to account for its broad substrate promiscuity, and (iv) TnmH as a biocatalyst enables the development of novel conjugation strategies to prepare antibody-TNM conjugates. These findings should greatly facilitate the construction and evaluation of antibody-TNM conjugates as next-generation ADCs for targeted chemotherapy.

Pyrazine compound and application thereof

The invention discloses a pyrazine compound and application thereof. In particular, the present invention provides a compound represented by the formula (I), wherein the extractant composed of the compound has a high extraction rate for lithium ions, and the organic phase is easy to enrich lithium-7 isotopes, so as to realize the extraction and separation of lithium isotopes.

Synthesis method of anthraquinone derivatives and tetracenedione derivatives through benzannulation reaction

The present invention relates to a method for synthesizing anthraquinone derivatives and tetracene dione derivatives through a benzannulation reaction, which presents a novel synthesis method, capable of processing synthesis easily, conveniently, and efficiently under mild conditions by an organic catalyst. The synthesis method uses an L-proline catalyst which is nontoxic, economical and easily available, compared to conventional production methods, thereby providing the anthraquinone derivatives and the tetracene dione derivatives through the one-pot benzannulation reaction of an α, β-unsaturated aldehyde compound, various 1,4-naphthoquinone compounds or 1,4-anthracenedione compounds. Various forms of anthraquinone derivatives or tetracene dione derivatives prepared by the synthesis method can be widely used for synthesis of natural products, dyes, and pharmaceutical products.COPYRIGHT KIPO 2017

Organocatalyzed benzannulation for the construction of diverse anthraquinones and tetracenediones

An efficient one-pot synthesis of anthraquinones and tetracenediones was achieved vial-proline catalyzed [4+2] cycloaddition of in situ generated azadiene from α,β-unsaturated aldehydes and 1,4-naphthoquinones or 1,4-anthracenedione in good to excellent yield. This protocol constitutes an unprecedented tandem benzannulation that allows one-pot construction of diverse anthraquinones and tetracenediones in the presence of organocatalysts. This methodology was applied successfully to the synthesis of naturally occurring molecules and photochemically interesting phenanthrenequinone derivatives.

Synthesis of functionalized 1,4-dihydro-9,10-anthraquinones and anthraquinones by ring closing metathesis using Grubbs' catalyst

A general and straightforward synthesis of anthraquinones was developed, in which diallylation of 1,4-naphthoquinones, followed by Ring Closing Metathesis (RCM) of the resulting diallylnaphthoquinones with Grubbs' catalyst and subsequent dehydrogenation using Pd/C afforded the desired anthraquinones with regiocontrol of substituents and in good yields.

A New Convenient Synthesis of Alkoxyanthracenes from Alkoxy-9,10- anthraquinones

Methoxy-9,10-anthraquinones with mono-, di- and tetraether groups at different positions 1a-h can be directly reduced to the corresponding methoxyanthracenes 3a-h in moderate to good yields by zinc in refluxing acetic acid. Under similar conditions, ethyl 1′-anthracenoxyacetate (3i) with the ester group unaffected and 1,8-oxybis(ethyleneoxyethyleneoxy)anthracene (5) were also conveniently synthesized in 65 and 70% yields, respectively.

Intramolecular reactivity of 1-alkoxyanthronylidenes. Disproportionation (set) of carbene-derived 1,5-biradicals

Photolyses of 1-alkoxy-9-diazoanthrones 12 in benzene induce abstraction of hydrogen from the side chain, followed by cyclization (→ 15 → 16) or disproportionation (→ 17 + 18) of the intervening biradicals 20. In alcohols, reduction of triplet anthronylidenes (314 → 21 → 22) competes with the formation of 20, and intramolecular electron transfer of 20 leads eventually to the acetals 24.

Preparation of Anthraquinones from 10-Hydroxy-9-anthracenecarbonitriles Obtained from a Novel Aryne Annulation Reaction

A new method for brief regioselective synthesis of anthraquinones via the reaction of anions of ethyl cyanoacetate or the anions of 2-(carbethoxyaryl)acetonitriles with arynes is described.