10228-90-7

Basic information

• Product Name: 9-methoxyacridine
• Synonyms: 9-methoxyacridine;Acridine, 9-methoxy-;Nsc 221435
• CAS NO: 10228-90-7
• Molecular Formula: C₁₄H₁₁NO
• Molecular Weight: 209.24
• Mol File: 10228-90-7.mol

Chemical Properties

• Boiling Point: 384.2°Cat760mmHg
• Flash Point: 139.7°C
• Appearance: /
• Density: 1.196g/cm³
• Vapor Pressure: 9.19E-06mmHg at 25°C
• Refractive Index: 1.688
• CAS DataBase Reference: 9-methoxyacridine(CAS DataBase Reference)
• NIST Chemistry Reference: 9-methoxyacridine(10228-90-7)
• EPA Substance Registry System: 9-methoxyacridine(10228-90-7)

Safety Data

• Hazardous Substances Data: 10228-90-7(Hazardous Substances Data)

Usage

Uses

Used in Research Applications:
9-methoxyacridine is used as a fluorescent dye for visualizing and studying cellular structures and processes in biological research. Its fluorescent properties allow for the tracking of molecules and monitoring of biochemical reactions.
Used in Pharmaceutical Development:
9-methoxyacridine is used as a potential therapeutic agent for the development of anticancer and antibacterial drugs. Its demonstrated properties make it a candidate for further research and development in the medical field.
Used in Organic Compound Preparation:
9-methoxyacridine is used as a key component in the synthesis of various organic compounds, contributing to the advancement of organic chemistry and the creation of new materials and substances.
Used in Industrial Applications:
9-methoxyacridine is utilized in the production of pharmaceuticals, where its unique properties can enhance the effectiveness and functionality of various medications.

InChI:InChI=1/C14H11NO/c1-16-14-10-6-2-4-8-12(10)15-13-9-5-3-7-11(13)14/h2-9H,1H3

Upstream product

• 110-71-4 1,2-dimethoxyethane 
• 578-95-0 10H-acridin-9-one 
• 67-56-1 methanol 
• 1207-69-8 9-Chloroacridine 
• 124-41-4 sodium methylate 

Downstream Products

• 578-95-0 10H-acridin-9-one 
• 5326-19-2 acridine-9-carbonitrile 
• 22739-29-3 N-methyl-9-acridinamine 
• 55468-69-4 N-(acridin-9-yl)glycine 
• 80129-86-8 N-(Phenylmethyl)-9-acridinamine 
• 719-54-0 10-methyl-9, 10-dihydro-9-acridinone 
• 67-56-1 methanol 
• 37070-64-7 acridin-9-yl(phenyl)methanone 
• 58880-43-6 10-carboxymethylacridanone sodium salt 
• 97869-49-3 acridin-9-yl-malononitrile 
• 130198-70-8 Acridin-9-yl-(4-{4-[bis-(2-chloro-ethyl)-amino]-benzenesulfonyl}-butyl)-amine 
• 130198-69-5 Acridin-9-yl-(3-{4-[bis-(2-chloro-ethyl)-amino]-benzenesulfonyl}-propyl)-amine 
• 130198-68-4 Acridin-9-yl-(2-{4-[bis-(2-chloro-ethyl)-amino]-benzenesulfonyl}-ethyl)-amine 
• 130031-50-4 Acridin-9-yl-(4-{4-[bis-(2-chloro-ethyl)-amino]-phenylsulfanyl}-butyl)-amine 

Relevant articles and documents

9-substituted acridines. Demethoxylation of 9-methoxyacridine and dechlorination of 9-chloroacridine in hydroxylic solvents

In methanol-water mixtures containing sodium or potassium hydroxide (up to 2.00M) the demethoxylation of 9-methoxyacridine to 9-acridone is of first order in both the free form of 9-methoxyacridine and the hydroxyl ion. The rate of the reaction is increased with an increase in the concentration of water. Sodium perchlorate has a small retarding effect on the reaction. In methanol-water mixtures containing perchloric or hydrochloric acid (up to 3.45M) the demethoxylation is of first order with respect to the protonated form of 9-methoxyacridine. The rate of the reaction decreases with an increase in the concentration of the acid or of sodium perchlorate, but when the concentration of water is increased (≈1.7 to 50M) and that of the acid is not changed, it reaches a maximum value in mixtures containing 8 to 10M-water. The dechlorination of 9-chloroacridine to 9-methoxyacridine in methanol containing sodium hydroxide or methoxide (up to 0.31M) is of first order in both the 9-chloroacridine and the hydroxyl or methoxyl ions.

Spectrophotometric determination of cycloserine with 9-methoxyacridine

Spectrophotometric assay for cycloserine based on the interaction of the drug with 9-methoxyacridine as a chromogenic agent is described. The highly colored substituted acridine product was identified as 9-(d-4-imino-3-isoxazolidinone)acridine. Color development was affected by time and temperature of heating and by the quantity of 9-methoxyacridine reagent utilized. The absorbance at 438 nm is linearly proportional to concentrations cycloserine with a detection limit of 0.3 μg/mL. The optimum range for the assay of cycloserine was from 5.0 x 10-6 to 3.0 x 10-4 M (correlation coefficient = 0.9999, n = 6). When applied to cycloserine capsules labeled to contain 250 mg, the proposed method gave mean recoveries of 101.84 ± 0.48%. The procedure is sufficiently sensitive, precise, and accurate for the determination of cycloserine in its dosage form.

Chemiluminescence Involving Acidic and Ambident Ion Light Emitters. The Chemiluminescence of the 9-Acridinepercarboxylate Anion

The reaction of phenyl 9-acridinecarboxylate (1) with an excess of peroxide ion in THF/water (67/33 mol percent) leads to the emission of either bright yellow-green light or bright blue light, depending on the reaction conditions.The blue emission is favored by high concentrations of hydrogen peroxide and water, for example. 9-Acridinepercarboxylic acid is a common intermediate in the reactions.The light emitter responsible for the blue chemiluminescence is acridone, whereas that responsible for the yellow-green chemiluminescence is the anion of acridone.The effects of base concentration and solvent composition on the relative proportions of these two emitters have produced evidence that, contrary to the expectation of simple theory, a dioxetanone is not an intermediate in the reaction.Other cases where chemiluminescence may involve percarboxylate and peroxide ions are discussed.

Palladium-catalyzed intermolecular decarboxylative coupling of 2-phenylbenzoic acids with alkynes via C-H and C-C bond activation

A novel protocol for palladium-catalyzed intermolecular formal [4 + 2] annulation of 2-phenylbenzoic acids with alkynes is described. Acridine is shown to be essential for the high reaction efficiency. Phenanthrene derivatives are formed in moderate to good yields without coupling (pseudo)halides or organometallic species.

Triethyloxonium tetrafluoroborate/l,2-dimethoxyethane -a versatile substitute for trimethyloxonium tetrafluoroborate in 0-methylation reactions

The triethyloxonium tetrafluoroborate/l,2-dimethoxyethane (TEO/DME) mixture is a versatile and cheap substitute for trimethyloxonium tetrafluoroborate in O-methylations of pyrrolin-2-ones, quinolones, acridones, and 1-oxo-β-carbolines. Undesired O-ethylat

Sulfonated diarylrhodamine dyes

Sulfonated diarylrhodamine compounds are useful as fluorescent labels of nucleosides, nucleotides, polynucleotides, and polypeptides. The compounds find particular application in the area of fluorescent nucleic acid analysis, e.g., automated DNA sequencing and fragment analysis, detection of probe hybridization in hybridization arrays, detection of nucleic acid amplification products, and the like.

On the thermally induced rearrangement of 2-alkoxypyridines to N-alkylpyridones

Analogues of 2-methoxypyridine undergo rearrangement to N-methylpyridones under flash vacuum pyrolysis (FVP) conditions. Ethoxy derivatives undergo competitive ethyl migration and elimination of ethylene. Analogues of 4-methoxypyridine do not undergo rearrangement under FVP conditions, but demethylation on silica may occur. The ease of rearrangement follows the basicity of the alkoxyhetarene to some extent. The vapour-phase rearrangements have been contrasted to condensed-phase pyrolyses. and a four-centre transition state for the former is supported by computation. The rearrangement allows structural assignment to the two products from the reaction of 2,4-dichloroquinoline with pyrrolidine.