885-23-4

Basic information

• Product Name: 9-acridinecarboxaldehyde
• Synonyms: 9-acridinecarboxaldehyde;acridine-9-carbaldehyde;ACRIDINE-9-CARBOXALDEHYDE;Acridin-9-carbaxaldehyde
• CAS NO: 885-23-4
• Molecular Formula: C₁₄H₉NO
• Molecular Weight: 207.23
• Mol File: 885-23-4.mol
• Article Data: 5

Chemical Properties

• Melting Point: 144-149°C
• Boiling Point: 416.4 °C at 760 mmHg
• Flash Point: 211.7 °C
• Appearance: /
• Density: 1.274g/cm³
• Vapor Pressure: 3.84E-07mmHg at 25°C
• Refractive Index: 1.758
• Storage Temp.: 2-8°C
• PKA: 2.70±0.10(Predicted)
• CAS DataBase Reference: 9-acridinecarboxaldehyde(CAS DataBase Reference)
• NIST Chemistry Reference: 9-acridinecarboxaldehyde(885-23-4)
• EPA Substance Registry System: 9-acridinecarboxaldehyde(885-23-4)

Safety Data

• Hazard Codes: Xn
• Statements: 22-36
• Safety Statements: 26
• WGK Germany: 3
• Hazardous Substances Data: 885-23-4(Hazardous Substances Data)

Usage

General Description

9-acridinecarboxaldehyde is a chemical compound with the molecular formula C15H11NO. It is a yellow solid with a distinct acridine odor. 9-acridinecarboxaldehyde is often used as a fluorescent dye and has been found to have antimicrobial and antifungal properties. It is also utilized as a reagent in organic synthesis and as a precursor for the production of other acridine derivatives. Additionally, 9-acridinecarboxaldehyde has been studied for its potential applications in medicine, particularly as an anti-cancer agent and in the development of new pharmaceutical drugs. Overall, this compound has a wide range of uses and potential benefits in various fields of science and industry.

InChI:InChI=1/C14H9NO/c16-9-12-10-5-1-3-7-13(10)15-14-8-4-2-6-11(12)14/h1-9H

Upstream product

• 298-46-4 carbamazepin 
• 256-96-2 dibenzoazepine 
• 36507-30-9 carbamazepine 10,11-epoxide 

Downstream Products

• 130161-06-7 acridine-9-N-(p-ethoxyphenyl)formimidoyl 
• 76062-64-1 benzophenone-9-acridinealdehyde azine 
• 95293-90-6 4-acridin-9-ylmethylene-2-phenyl-4H-oxazol-5-one 
• 102160-35-0 acridine-9-carbaldehyde-(2,4-dinitro-phenylhydrazone) 
• 102555-03-3 acridine-9-carbaldehyde-(4-nitro-phenylhydrazone) 
• 61864-84-4 acridine-9-carbaldehyde phenylhydrazone 
• 22192-31-0 (2E)-3-(acridin-9'-yl)-1-phenylprop-2-en-1-one 
• 94463-85-1 acridin-9-ylmethylen-aniline 
• 6285-36-5 1-acridin-9-yl-4-dibutylamino-butan-1-ol 
• 802-20-0 N'-acridin-9-ylmethylene-N,N-dimethyl-p-phenylenediamine 
• 59959-14-7 N-acridin-9-ylmethylene-aniline N-oxide 
• 103280-69-9 2-[acridin-9-yl-(6-imino-3-methoxy-cyclohexa-2,4-dienylidene)-methyl]-4-methoxy-aniline 
• 115292-76-7 2-[acridin-9-yl-(6-imino-3-methyl-cyclohexa-2,4-dienylidene)-methyl]-4-methyl-aniline 
• 103167-49-3 acridin-9-ylmethylene-biphenyl-4-yl-amine 

Relevant articles and documents

Online Investigation of Aqueous-Phase Electrochemical Reactions by Desorption Electrospray Ionization Mass Spectrometry

Electrochemistry (EC) combined with mass spectrometry (MS) is a powerful tool for elucidation of electrochemical reaction mechanisms. However, direct online analysis of electrochemical reaction in aqueous phase was rarely explored. This paper presents the online investigation of several electrochemical reactions with biological relevance in the aqueous phase, such as nitrosothiol reduction, carbohydrate oxidation, and carbamazepine oxidation using desorption electrospray ionization mass spectrometry (DESI-MS). It was found that electroreduction of nitrosothiols [e.g.; nitrosylated insulin B (13-23)] leads to free thiols by loss of NO, as confirmed by online MS analysis for the first time. The characteristic mass shift of 29 Da and the reduced intensity provide a quick way to identify nitrosylated species. Equally importantly, upon collision-induced dissociation (CID), the reduced peptide ion produces more fragment ions than its nitrosylated precursor ion (presumably the backbone fragmentation cannot compete with the facile NO loss for the precursor ion), thus facilitating peptide sequencing. In the case of saccharide oxidation, it was found that glucose undergoes electro-oxidation to produce gluconic acid at alkaline pH, but not at neutral and acidic pHs. Such a pH-dependent electrochemical behavior was also observed for disaccharides such as maltose and cellobiose. Upon electrochemical oxidation, carbamazepine was found to undergo ring contraction and amide bond cleavage, which parallels the oxidative metabolism observed for this drug in leucocytes. The mechanistic information of these redox reactions revealed by EC/DESI-MS would be of value in nitroso-proteome research and carbohydrate/drug metabolic studies.

Synthesis of 2,4-Diamino-6-[2′-O-(ω -carboxyalkyl)oxydibenz[b,f]azepin-5-yl]-methylpteridines as Potent and Selective Inhibitors of Pneumocystis carinii, Toxoplasma gondii, and Mycobacterium avium Dihydrofolate Reductase

Six previously undescribed N-(2,4-diaminopteridin-6-yl)methyldibenz[b,f]azepines with water-solubilizing O-carboxyalkyloxy or O-carboxybenzyloxy side chains at the 2′-position were synthesized and compared with trimethoprim (TMP) and piritrexim (PTX) as i

The Metabolism of Carbamazepine in Humans: Steric Course of the Enzymatic Hydrolysis of the 10,11-Epoxide

Carbamazepine 10,11-oxide (1a,10b-dihydro-6H-dibenzooxirenoazepine-6-carboxamide), a key intermediate in carbamazepine metabolism, was found to be unusually resistant to enzymatic hydrolysis when incubated with microsomal and cytosolic fractions from rabbit, rat, and guinea pig livers.However, its hydrolysis product, trans-10,11-dihydro-10,11-dihydroxy-5H-dibenzoazepine-5-carboxamide, was excreted, as previously reported, both in the free and in conjugated forms, as the main metabolite in the urine of humans under carbamazepine treatment.The free diol and that obtained after treatment with β-glucuronidase/arylsulfatase were both found by Mosher's method to be formed in an enantiomeric excess of 80percent, the prevalent enantiomer having the (-)-10S,11S absolute configuration, as determined by applying the CD exciton coupling method to its bis ester.This finding confirms the pronounced enantioselectivity of the microsomal epoxide hydrolase toward meso and racemic substrates, but is in contrast with the prevalent formation of (R,R)-diols in most other known cases of enzymatic hydrolysis of epoxides.Preparatively useful syntheses of the racemic trans-10,11-dihydro-10,11-diol and of 9-(hydroxymethyl)-10-carbamoylacridan, another carbamazepine metabolite, are reported for the first time.