5132-81-0

Basic information

• Product Name: Methyl 9-Acridinecarboxylate
• Synonyms: 9-Acridinecarboxylic Acid Methyl Ester;Methyl 9-Acridinecarboxylate
• CAS NO: 5132-81-0
• Molecular Formula: C₁₅H₁₁NO₂
• Molecular Weight: 237.25
• Product Categories: Aromatics Compounds;Aromatics;Heterocycles
• Mol File: 5132-81-0.mol

Chemical Properties

• Boiling Point: 413.6°C at 760 mmHg
• Flash Point: 204°C
• Appearance: /
• Density: 1.256g/cm³
• Vapor Pressure: 4.72E-07mmHg at 25°C
• Refractive Index: 1.685
• Solubility: Chloroform
• CAS DataBase Reference: Methyl 9-Acridinecarboxylate(CAS DataBase Reference)
• NIST Chemistry Reference: Methyl 9-Acridinecarboxylate(5132-81-0)
• EPA Substance Registry System: Methyl 9-Acridinecarboxylate(5132-81-0)

Safety Data

• Hazardous Substances Data: 5132-81-0(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
Methyl 9-Acridinecarboxylate is used as a synthetic intermediate for the production of various organic compounds. Its chemical structure allows it to be a versatile component in the synthesis of a wide range of molecules, including pharmaceuticals, dyes, and other specialty chemicals.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, Methyl 9-Acridinecarboxylate is used as a key component in the development of new drugs. Its unique chemical properties make it a valuable asset in the design and synthesis of novel therapeutic agents, potentially leading to the discovery of new treatments for various diseases and medical conditions.
Used in Dye Manufacturing:
Methyl 9-Acridinecarboxylate is also utilized in the manufacturing of dyes, where its yellow solid form contributes to the color properties of the final product. Its use in this industry highlights the compound's versatility and the broad range of applications it can be employed in.
Used in Research and Development:
In addition to its practical applications, Methyl 9-Acridinecarboxylate is also used in research and development settings. Scientists and chemists employ Methyl 9-Acridinecarboxylate to study its properties and explore its potential in creating new materials and compounds with unique characteristics and applications.

InChI:InChI=1/C15H11NO2/c1-18-15(17)14-10-6-2-4-8-12(10)16-13-9-5-3-7-11(13)14/h2-9H,1H3

Upstream product

• 186581-53-3 diazomethane 
• 5336-90-3 acridine-9-carboxylic acid 
• 67-56-1 methanol 
• 66074-67-7 9-acridinecarbonyl chloride 
• 723-89-7 1-phenyl-indole-2,3-dione 
• 74-88-4 methyl iodide 
• 622-37-7 Phenyl azide 

Downstream Products

• 1070672-22-8 10-benzyl-9-methoxycarbonylacridinium trifluoromethanesulfonate 
• 153562-08-4 9-Bromomethyl-10-methyl-9,10-dihydro-acridine-9-carboxylic acid ethyl ester 
• 153562-07-3 9-ethoxycarbonyl-10-methylacridane 
• 52249-32-8 N-methyldibenzazepine 
• 5132-82-1 9-[(carbonyl)methoxy]-10-methylacridinium methylsulfate 

Relevant articles and documents

Metal Ion Assisted DNA-Intercalation of Crown Ether-linked Acridine Derivatives

Crown ether linked DNA-intercalators have shown an enhanced binding ability to DNA in the presence of certain kinds of metal ions, due to a cationic property given by the co-ordination of the crown ether moiety to the metal ions.

Acid-promoted synthesis and photophysical properties of substituted acridine derivatives

A simple and efficient synthetic protocol for the preparation of acridinium esters and amides through the cyclization and esterification or amidation of isatins with alcohols or amines as nucleophiles in the presence of CF3SO3H is established. A series of polycyclic acridine derivatives bearing large π-conjugated systems were obtained in high yields, including some key intermediates for the synthesis of biologically active molecules. The photophysical properties of these synthesized acridines were investigated, demonstrating that the sulfur heterocyclic acridine 9w was obtained in a high quantum yield. This journal is

Method for preparing 9-hydroxymethyl-9,10-dihydracridine

The invention relates to a method for preparing 9-hydroxymethyl-9,10-dihydracridine. The preparation method comprises the following steps: carrying out a reduction reaction on acridine esters shown as a formula (I) in a solvent containing a Lewis acid and a reducing agent so as to produce the 9-hydroxymethyl-9,10-dihydracridine. In the formula (I), R is C1-3 alkyl. The method for preparing 9-hydroxymethyl-9,10-dihydracridine provided by the invention has the advantages that the acridine esters serve as initial raw materials, and due to selection of the raw materials, ester groups and carbon-nitrogen double bonds having equivalent reduction difficulty participate in the reduction reaction, so that selectivity of the reduction reaction is improved, side reactions are reduced, and the reaction yield is improved.

Structure, formation, thermodynamics and interactions in 9-carboxy-10-methylacridinium-based molecular systems

9-Carboxy-10-methylacridinium chloride and trifluoromethanesulfonate, the parent compounds for a wide range of chemiluminogenic salts of practical importance, were synthesized and thoroughly investigated to address problems concerning structural and thermodynamical issues of these cognitively interesting molecular systems. Under various conditions of crystallization, the title salts disclosed three types of crystals: one built from the monomeric form of cations and two containing homoconjugated cations. The title compounds made the first described derivatives of acridine, expressing homoconjugated cationic forms, both in crystalline solid and gaseous phases. The monocrystals were characterized, employing X-ray crystallography and spectroscopic methods such as MALDI-TOF MS, ESI-QTOF MS, NMR and UV-Vis. X-ray crystallography studies revealed the occurrence of the three different molecular architectures, in which not only the counter ions and stoichiometry are different, but also the space group and number of molecules in the unit cell. The energetics and intermolecular interactions occurring within the crystals were explored, applying crystal lattice energy calculations and Hirshfeld surface analysis. In order to elucidate the thermodynamics and origin of the experimentally revealed forms, computations based on the density functional theory were performed, assuming vapour and liquid phases.

Facile synthesis of unsymmetrical acridines and phenazines by a Rh(III)-catalyzed amination/cyclization/aromatization cascade

We report formal [3 + 3] annulations of aromatic azides with aromatic imines and azobenzenes to give acridines and phenazines, respectively. These transformations proceed through a cascade process of Rh(III)-catalyzed amination followed by intramolecular electrophilic aromatic substitution and aromatization. Acridines can be directly prepared from aromatic aldehydes by in situ imine formation using catalytic benzylamine.

Diphenylmethylene hydroxamic acids as selective class IIa histone deacetylase inhibitors

We have identified a series of diphenylmethylene hydroxamic acids as novel and selective HDAC class IIa inhibitors. The original hit, N-hydroxy-2,2-diphenylacetamide (6), has sub-micromolar class IIa HDAC inhibitory activity, while the rigidified oxygen a

INHIBITORS OF HISTONE DEACETYLASE

This invention relates to compounds for the inhibition of histone deacetylase. More particularly, the invention provides for compounds of formula compounds of the Formula (I) and N-oxides, hydrates, solvates, pharmaceutically acceptable salts, prodrugs and complexes thereof, and racemic and scalemic mixtures, diastereomers and enantiomers thereof, wherein groups L, M, X and Y are as defined herein.

Ultra-Sensitive Chemiluminescent Substrates for Enzymes and Their Conjugates

New chemiluminescent compounds, stable in aqueous buffers, for use in biological assaying include acridanebased compounds and (1,2)-dioxetanes. Among the new acridanebased compounds are water-soluble acridanes, enhancer coupled acridanes, bis and trisacri

A Free Radical Route to the Benzazepines and Dibenzazepines

Free radical ring expansion of six membered azocycles provides a new entry to the preparation of benzazepines and dibenzazepines.

N-arylation of isatins

A process for the N-arylation of isatins with organo bismuth reagents is disclosed.