602-69-7

Basic information

• Product Name: 9,10-DIOXO-9,10-DIHYDRO-ANTHRACENE-1-CARBOXYLIC ACID
• Synonyms: 1-Anthraquinonecarboxylic acid;9,10-Dihydro-9,10-dioxo-1-anthracenecarboxylic acid;9,10-Dioxo-9,10-dihydro-1-anthracenecarboxylic acid;α-Anthraquinonecarboxylic acid
• CAS NO: 602-69-7
• Molecular Formula: C₁₅H₈O₄
• Molecular Weight: 252.22
• Mol File: 602-69-7.mol

Chemical Properties

• Boiling Point: 513°C at 760 mmHg
• Flash Point: 278.2°C
• Appearance: /
• Density: 1.469g/cm³
• Vapor Pressure: 2.38E-11mmHg at 25°C
• Refractive Index: 1.69
• CAS DataBase Reference: 9,10-DIOXO-9,10-DIHYDRO-ANTHRACENE-1-CARBOXYLIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: 9,10-DIOXO-9,10-DIHYDRO-ANTHRACENE-1-CARBOXYLIC ACID(602-69-7)
• EPA Substance Registry System: 9,10-DIOXO-9,10-DIHYDRO-ANTHRACENE-1-CARBOXYLIC ACID(602-69-7)

Safety Data

• Hazardous Substances Data: 602-69-7(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
9,10-DIOXO-9,10-DIHYDRO-ANTHRACENE-1-CARBOXYLIC ACID is used as a building block for the synthesis of various pharmaceutical drugs. Its unique structure allows for the development of new drug candidates with potential therapeutic applications.
Used in Agrochemical Industry:
In the agrochemical industry, 9,10-DIOXO-9,10-DIHYDRO-ANTHRACENE-1-CARBOXYLIC ACID is used as a precursor in the synthesis of agrochemicals, such as pesticides and herbicides. Its reactivity and stability contribute to the development of effective and environmentally friendly products.
Used in Materials Industry:
9,10-DIOXO-9,10-DIHYDRO-ANTHRACENE-1-CARBOXYLIC ACID is used as a component in the development of advanced materials, such as dyes and pigments. Its chemical properties enable the creation of materials with specific color characteristics and stability.
Used in Organic Chemistry Reactions:
As a reagent in organic chemistry, 9,10-DIOXO-9,10-DIHYDRO-ANTHRACENE-1-CARBOXYLIC ACID is utilized in various reactions, such as esterification, amidation, and condensation. Its versatility and reactivity make it a valuable tool in the synthesis of complex organic compounds.
It is crucial to handle and store 9,10-DIOXO-9,10-DIHYDRO-ANTHRACENE-1-CARBOXYLIC ACID with care, as it can pose hazards if not used or stored properly. Proper safety measures and precautions should be taken to ensure the safe use of 9,10-DIOXO-9,10-DIHYDRO-ANTHRACENE-1-CARBOXYLIC ACID in various applications.

InChI:InChI=1/C15H8O4/c16-13-8-4-1-2-5-9(8)14(17)12-10(13)6-3-7-11(12)15(18)19/h1-7H,(H,18,19)

Upstream product

• 82-05-3 7H-benz[d,e]anthracene-7-one 
• 79-37-8 oxalyl dichloride 
• 120-12-7 anthracene 
• 64-19-7 acetic acid 
• 10028-15-6 ozone 
• 954-07-4 1-methylanthraquinone 
• 7697-37-2 nitric acid 
• 613-12-7 2-methylanthracene 
• 82-03-1 2-Methylbenzanthrone 
• 607-42-1 anthracene-1-carboxylic acid 
• 6373-11-1 aceanthrenequinone 
• 7664-93-9 sulfuric acid 
• 860520-19-0 7-oxo-7H-benz[de]anthracene-1-carboxylic acid 
• 861529-42-2 3-methyl-2,3-dihydro-benz[de]anthracen-7-one 

Downstream Products

• 112022-06-7 9,10-Dioxo-9,10-dihydro-anthracene-1-carboxylic acid (2-dimethylamino-ethyl)-amide 
• 632-83-7 1-Bromoanthraquinone 
• 607-42-1 anthracene-1-carboxylic acid 
• 861075-95-8 1-(α-hydroxy-benzhydryl)-anthraquinone 
• 859938-60-6 Hydroxy-diphenyl-(9.10-dihydro-anthryl-⁽¹⁾)-methan 
• 132653-13-5 1-benzhydryl-anthraquinone 
• 859074-03-6 1-benzhydryl-9,10-dihydro-anthracene 
• 876483-46-4 9-phenyl-naphth[3,2,1-de]anthracen-5-one 
• 861608-30-2 1-(4-methoxy-benzoyl)-anthraquinone 
• 61726-79-2 1-benzoylanthraquinone 
• 860587-77-5 2-p-tolyl-anthra[9,1-bc]furan-6-one 
• 91323-95-4 2-phenyl-6H-anthra<9,1-bc>furan-6-one 
• 57449-82-8 8-amino-2-phenyl-2H-dibenzo[de,h]cinnoline-3,7-dione 
• 25308-58-1 methyl anthranylate 

Relevant articles and documents

1-(Methylamino)anthracene – An Accessible Building Block for Photoresponsive Compounds

In this paper we present a convenient and scalable synthesis of 1-(methylamino)anthracene, which is a potent building block for the construction of photoresponsive materials. With this structural motif we have synthesized an anion receptor bearing two anthracene groups. Interaction of a chloride anion with the anthracene moieties increases the association constant. Photocycloaddition allows to obtain a single macrocyclic receptor, which exhibits higher binding constants due to the macrocyclic effect.

COMPLEXATION OF AROMATIC CARBOXYLIC ACIDS WITH HEPTAKIS(2,6-DI-O-METHYL)CYCLOMALTOHEPTAOSE IN CHLOROFORM AND WATER

Complexation of various aromatic carboxylic acids with heptakis(2,6-di-O-methyl)cyclomaltoheptaose (DM-βCD) in chloroform and water has been studied by u.v. absorption, induced c.d., and n.m.r. spectroscopy.The inclusion complex of dimethylaminobenzoic acid is axial in water but equatorial or lid-type in chloroform, that of anthracene-9-carboxylic acid is axial in water and equatorial in chloroform, that of pyrene-1-carboxylic acid is lid-type in water at pH 9.0, and that of ferrocenecarboxylic acid depends on the dissociation of the carboxyl group.

X-ray crystal structures of two solvent complexes involving positionally isomeric 9,10-anthraquinonecarboxylic acids and DMSO

Two constitutionally isomeric 9,10-anthraquinonecarboxylic acids 1 and 2 are reported to yield DMSO-solvated crystals (1a and 2a) on the crystallization from DMSO. The molecular and crystal structures are described and comparatively discussed with reference to the effect implicated by the different position of the carboxylic group at the anthraquinone basis and the involvement of the solvent molecule.

Photoisomerization and Photocyclization Reactions of 1-Styrylanthracene

On triplet sensitization, 1-styrylanthracene (1SA) undergoes adiabatic cis->trans one-way isomerization (3c*->3t*) similarly to 2-anthrylethylenes.However, upon direct irradiation, cis-1SA in the singlet excited state mostly undergoes cyclization to a dihydrophenanthrene-type product (DHP), 4a,4b-dihydrobenzochrysene, competing with an inefficient intersystem crossing to 3c* followed by one-way isomerization.The produced DHP, in deaerated benzene, is reverted to cis-1SA by a thermal (Ea = 14.9 kcal mol-1) or a photochemical pathway; however, under an oxygenated atmosphere DHP gives benzochrysene.A failure in the production of a cyclized product upon the excitation of trans-1SA shows that the isomerization really takes place in a one-way fashion.

2-[(arylmethyl)amino]-2-methyl-1,3-propanediol DNA intercalators. An examination of the effects of aromatic ring variation on antitumor activity and DNA binding

The effects of variation of aromatic ring size, shape, and side-chain position on antitumor activity and DNA binding in a series of carbocyclic 2-[(arylmethyl)amino]-2-methyl-1,3-propanediols (AMAPs) were examined. In general, the interaction of AMAPs wit

Anthracene derivatives

The present invention relates to compounds of formula (I) or a monomethyl or a monoethyl ether thereof (the compound of formula (I) including these ethers may contain no more than 30 carbon atoms in total); ethers, esters thereof; acid addition salts thereof; wherein Ar is an anthracene or substituted anthracene ring system; R1 contains not more than eight carbon carbon atoms and is a group STR1 wherein m is 0 or 1; R5 is hydrogen; R6 and R7 are the same or different and each is hydrogen or C1-3 alkyl optionally substituted by hydroxy; R8 and R9 are the same or different and each is hydrogen or C1-3 alkyl; --C--C-- is a five- or six-membered saturated carbocyclic ring; R10 is hydrogen, methyl or hydroxymethyl; R11, R12 and R13 are the same or different and each is hydrogen or methyl; R14 is hydrogen, methyl, hydroxy, or hydroxymethyl.

Pigment composition

A pigment composition contains a pigment and a dispersant. The dispersant is a phosphoric ester compound represented by the following general formula: wherein at least one of the three Rs is a residuum of a polyester chain containing as principal bonds thereof ester bonds of a polycarboxylic acid and a polyalcohol.

Pigment composition

A pigment composition contains a pigment and a dispersant. The dispersant is a polyester compound which contains, per molecule, a residuum of at least two benzene rings coupled together, an aromatic ring having at least 8 carbon atoms or a heterocyclic ring having at least 8 carbon atoms, and at least one ester bond as a principal bond.

Photoenolisation. XI. Photooxydation des o-methylbenzophenones

Photoenols 2 of 2- (1a), 2,4- (1b), 2,5- (1c), 2,6- (1d), 2,2'- (1e) and 2,3'-dimethylbenzophenones (1f) were trapped by (3)O2.When a 350 nm wavelength Hg lamp (Rayonet RPR 100) was used (benzene solution) with ketones 1a-c, the corresponding 2-formyl- 4 and 2-carboxybenzophenones 8 were formed as well as 3-phenyl-phtalides 10.Compounds 4 arose from dehydration of the intermediate endoperoxydes 3.Throught photoenolisation, 2-formylbenzophenones 4 gave the intermediate ketene-enols 5 which either isomerised to phtalides 10 or added oxygen to form the corresponding endoperoxydes 6; the latter isomerised to peracids 7, which, by reaction with aldehydes 4, yielded the carboxylic acids 8.When the aerated irradiations were performed simultaneously with 350 nm light and with light above 380 nm (Hanovia 679 A-36, benzene solution), ketones 1a-f yielded the same compounds 4, 8 and 10 but also anthraquinones 13.The latter arose from reversible cyclisation of photoenols 2 E giving dihydroanthranols 11 which were trapped by oxygen, yielding the anthrones 12 which were subsequently photooxidized to anthraquinones 13.With 2,6-dimethylbenzophenone (1d), the corresponding photoenols 2 were trapped for the first time.Compounds 8d, and 13d were absent, but instead 1-carboxyanthraquinone 15 was obtained.The latter can arise from 1-methylanthraquinone 13d trough photoenolisation-oxidation process alredy reported for this compound.With 2,2'-dimethylbenzophenone 1e, 3,3'-spirobiphtalide 14 was obtained instead 2-methyl-2'-carboxybenzophenone 8e; the latter, through a photoenolisation-oxidation process analogous to that described in the second paragraph, yielded 2,2'-dicarboxybenzophenone which underwent dehydration to compound 14.Under the same conditions (Hanovia) but in acetic acid solution, anthraquinones 13 were not formed with ketones 1a-f, due to rapid reketonisation of photoenols 2 E in this medium; however, compounds 4, 8, 10 and 14 were produced.Products 8, 10, 13, 14 and 15 were isolated and characterised or identified.Yields were deduced from actual weights of the isolated compounds (carboxylic acids 8 and 15) and from GLC determinations (compounds 4, 10, 13 and 14).

Aspects of Tautomerism: Part X - Neighbouring Group Effects on the Structure and Reactivity Patterns of Acid Chlorides

The influence of neighbouring groups on the structure and reactivity patterns of over one hundred acid chlorides derived from γ- and δ-keto acids, 1,2- and 1,3-dicarboxylic acid half-esters and diacid chlorides have been examined.Contrary to reports in the literature, text books and monographs, evidence has been obtained for the non-existence of tautomerism between the isomeric pairs of either acid chlorides or half-ester acid chlorides.ce.