4707-71-5

Usage

Uses

Used in Chemical Research and Development:
PHENANTHRENE-9-CARBOXALDEHYDE is used as a starting material for the synthesis of fluorescent probes due to its unique chemical properties and reactivity.
Used in Analytical Chemistry:
PHENANTHRENE-9-CARBOXALDEHYDE is used as a component in the creation of fluorescent probes for analytical chemistry applications, such as detecting and analyzing specific molecules or ions in complex samples.
Used in Biomedical Research:
In the field of biomedical research, PHENANTHRENE-9-CARBOXALDEHYDE is used as a building block for the development of fluorescent probes that can be employed in cellular imaging, drug discovery, and the study of biological processes.
Used in Environmental Science:
PHENANTHRENE-9-CARBOXALDEHYDE is utilized in the production of fluorescent probes for environmental science applications, including the detection and monitoring of pollutants and contaminants in various ecosystems.
Used in Material Science:
PHENANTHRENE-9-CARBOXALDEHYDE is employed in the development of fluorescent probes for material science, where they can be used to study the properties and behavior of new materials and their potential applications in various industries.

Purification Methods

Crystallise the aldehyde from EtOH and sublime it at 95-98o/0.07mm. The 2,4-dinitrophenylhydrazone has m 272-273o. [Beilstein 7 III 2532, 7 IV 1740.]

InChI:InChI=1/C15H10O/c16-10-12-9-11-5-1-2-6-13(11)15-8-4-3-7-14(12)15/h1-10H

Upstream product

• 85-01-8 phenanthrene 
• 408528-16-5 N-phenyl-9-phenanthrylcarboxamide 
• 38399-78-9 9-phenanthrenyllithium 
• 68-12-2 N,N-dimethyl-formamide 
• 71112-64-6 9-phenanthrylmagnesium bromide 
• 122-51-0 orthoformic acid triethyl ester 
• 109-94-4 formic acid ethyl ester 
• 219-92-1 dibenzocycloheptene 
• 546-67-8 lead(IV) tetraacetate 
• 71-43-2 benzene 
• 573-17-1 9-bromophenanthrene 
• 2591-86-8 N-Formylpiperidine 
• 883-20-5 9-methylphenanthrene 
• 4885-02-3 Dichloromethyl methyl ether 

Downstream Products

• 19893-76-6 5--4-nitro-penten-(4)-ylbenzoat 
• 724427-49-0 benzyl-[9]phenanthrylmethylen-amine 
• 21461-45-0 9-(2-nitro-vinyl)-phenanthrene 
• 51873-96-2 E-9-phenanthrenecarboxaldehyde oxime 
• 19893-69-7 1--2-nitro-penten-(1) 
• 19893-75-5 4--3-nitrobuten-(3)-ylacetat 
• 14134-06-6 9-ethenylphenanthrene 
• 17181-05-4 (E)-9-styrylphenanthrene 
• 62131-68-4 9-[(E)-2-(4-Methyl-naphthalen-1-yl)-vinyl]-phenanthrene 
• 19889-62-4 5--4-nitro-penten-(4)-ylacetat 
• 52988-13-3 9-[(E)-2-(8-Phenyl-naphthalen-2-yl)-vinyl]-phenanthrene 
• 52988-14-4 C₃₀H₂₄O 
• 13730-66-0 2-phenanthren-9-yl-4,5-diphenyl-1H-imidazole 
• 796874-03-8 (4-methoxyphenyl)(phenanthren-9-yl)methanol 

Relevant academic research and scientific papers

Bifunctional antitumor agents. Derivatives of pyrrolo[9,10-b]phenanthrene - A DNA intercalative delivery template

The preparation and intercalative ability of the pyrrolo[9,10-b]phenanthrene nucleus is described. Functionalization of the nucleus was achieved using standard indole chemistry. The utility of this template as a DNA intercalating drug delivery system is demonstrated by synthesis of a derived bis-chloroethylamine alkylating system and a hybrid DNA interactive enediyne system.

Enantioselective Lewis Acid Catalyzed ortho Photocycloaddition of Olefins to Phenanthrene-9-carboxaldehydes

Visible-light irradiation (λ=457 nm) enabled the enantioselective ortho photocycloaddition of olefins to phenanthrene-9-carboxaldehydes (15 examples, 46–93 % yield, 82–98 % ee). A chiral oxazaborolidine Lewis acid (20 mol %) was employed as the catalyst. It operates by coordination to the aldehyde inducing a bathochromic absorption shift beyond the nπ* absorption of the uncomplexed aldehyde. At long wavelengths the Lewis acid complex is exclusively excited; within the complex, one enantiotopic face of the aromatic aldehyde is efficiently shielded. Lewis acid coordination also alters the type selectivity and the simple diastereoselectivity of the photocycloaddition.

Microwave-assisted Vilsmeier-Haack formylation of aromatic substrates

A microwave-assisted Vilsmeier-Haack formylation reaction has been studied on various amines, phenols and polynuclear hydrocarbons under solvent free condition that rapidly affords higher yield of products compared to traditional thermal condition.

Stereocontrolled synthesis of anticancer β-lactams via the Staudinger reaction

Stereocontrolled synthesis of novel β-lactams using polyaromatic imines following the Staudinger reaction has been accomplished. The effects of domestic microwave irradiation on this type of reaction have been investigated. Formation of trans-β-lactams has been explained through isomerization of the enolates formed during the reaction of acid chloride (equivalent) with imines in the presence of triethylamine. A donor-acceptor complex pathway is believed to be involved in the formation of cis-β-lactams. The effect of a peri hydrogen has been found to be significant in controlling the stereochemistry of the resulting β-lactams. SAR has identified β-lactams with anticancer activity. The presence of an acetoxy group has proven obligatory for their anticancer activity.

Therapeutics for chemokine mediated diseases

The invention provides therapeutic and biological uses of chemokine-receptor-binding compounds (including chemokine receptor ligands such as chemokine receptor agonists or antagonists), such as tricyclic phenanthrene derivatives, including uses in the treatment of disease states mediated by chemokines. The relevant chemokines may for example be monocyte chemoattractant protein-one (MCP-1) or interleukin-8 (IL-8), and the relevant chemokine receptors may for example be corresponding chemokine receptors (CCR-2, CCR-4, CXCR-1, and CXCR-2). In other aspects, the invention provides corresponding pharamaceutical compositions and therapeutic methods. In one aspect, for example, the invention provides for the use of phenanthrene-9,10-dione in the treatment of multiple sclerosis.

Vilsmeier reagent for formylation in solvent-free conditions using microwaves

POCl3-DMF over silica gel has been used for the synthesis of β-chlorovinylaldehydes (1-5), 2-aryl-3-formylindoles (6-8), 2-chloro-3-formylquinolines (9-13) and other aromatic aldehydes (14-20) using solvent-free conditions and microwave irradiation.

A new method of acylation and formylation of polycyclic aromatic hydrocarbons

Polycyclic aromatic hydrocarbon radical anions, prepared by the addition of sodium to the aromatic hydrocarbon in THF, undergo acylation with carboxylic acid esters and formylation with N,N-dialkylformamides.

Barium Permanganate, Ba(MnO4)2, a versatile and mild oxidizing agent for use under aprotic and non-aqueous conditions

Barium Permanganate is an easily prepared, stable, and a versatile oxidation reagent. With this reagent different types of primary and secondary hydroxy compounds are converted to their carbonyl derivatives. Aldehydes could be transformed to their carboxylic acids. Benzylic chloride and bromides are converted to their aldehydes and carboxylic acids. Semicarbazide and 2,4-dinitrophenylhydrazine derivatives of benzylic carbonyl compounds undergo carbon-nitrogen bond cleavage selectively and yield the expected carbonyl compounds. p-Hydroquinone is converted to p-benzoguinone and aromatic amines to their azo compounds. Anthracene and phenanthrene produce their 9,10-quinones. Diphenyl acetylene and trans stilbene give benzil, and styrene produces benzaldehyde. Selective oxidations of secondary benzylic carbon-hydrogen bonds occur and the corres- ponding carbonyl compounds are produced in good yields.

Selective Oxidative Cleavage of Benzylic Carbon-Nitrogen Double Bonds Under Non-Aqueous Condition with Tetrakis(pyridine)-silver Dichromate 2Cr2O7

Carbonyl derivatives of phenylhydrazine, 2-nitrophenylhydrazine, 2,4-dinitrophenylhydrazine, semicarbozone, and hydroxylamine are converted to their corresponding carbonyl compounds with tetrakis(pyridine)silver dichromate in benzene.Selectivity is also observed for benzylic C=N cleavage.

BARIUM PERMANGANATE A USEFUL OXIDANT FOR THE SELECTIVE DEOXIMATION OF BENZYLIC OXIMES TO THEIR CORRESPONDING CARBONYL COMPOUNDS

Benzylic oximes are oxidized selectively with barium permanganate in refluxing acetonitrile and produce their corresponding carbonyl compounds in good yields.