10183-82-1

Basic information

• Product Name: N-phenylfluoren-9-imine
• Synonyms: N-phenylfluoren-9-imine;9-(PHENYLIMINO)FLUORENE
• CAS NO: 10183-82-1
• Molecular Formula: C₁₉H₁₃N
• Molecular Weight: 255.31
• Mol File: 10183-82-1.mol

Chemical Properties

• Boiling Point: 408°Cat760mmHg
• Flash Point: 193.1°C
• Appearance: /
• Density: 1.11g/cm³
• Vapor Pressure: 1.71E-06mmHg at 25°C
• Refractive Index: 1.644
• CAS DataBase Reference: N-phenylfluoren-9-imine(CAS DataBase Reference)
• NIST Chemistry Reference: N-phenylfluoren-9-imine(10183-82-1)
• EPA Substance Registry System: N-phenylfluoren-9-imine(10183-82-1)

Safety Data

• Hazardous Substances Data: 10183-82-1(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
N-phenylfluoren-9-imine is utilized as a building block in organic synthesis for the creation of functional materials and pharmaceuticals, leveraging its structural and chemical characteristics to contribute to the development of novel compounds.
Used in Optoelectronic Devices:
In the optoelectronics industry, N-phenylfluoren-9-imine is employed for its interesting electronic properties, which make it a valuable component in the design and fabrication of devices that rely on the interaction of light with electronic components.
Used in Organic Semiconductors:
N-phenylfluoren-9-imine also serves as a key component in the development of organic semiconductors, where its electronic properties are harnessed to enhance the performance of these materials in various electronic and optoelectronic applications.

InChI:InChI=1/C19H13N/c1-2-8-14(9-3-1)20-19-17-12-6-4-10-15(17)16-11-5-7-13-18(16)19/h1-13H

Upstream product

• 486-25-9 9-fluorenone 
• 62-53-3 aniline 
• 4440-33-9 fluorenone imine 
• 830-72-8 9H-fluorene-9-thione 
• 4535-09-5 N-phenyl-fluorenoneimine-N-oxide 
• 13248-13-0 2-(9-fluorenylidene)indane-1,3-dione 
• 86-73-7 9H-fluorene 
• 586-96-9 Nitrosobenzene 
• 88070-90-0 9-Anilino-9-acetyl-fluoren 
• 75-05-8 acetonitrile 
• 79817-36-0 9-(cyclopropylcarbonyl)-9-anilinofluorene 
• 622-37-7 Phenyl azide 
• 23695-65-0 adamantane-2-thione 
• 1976-60-9 9-(Phenylcarbamoyloximino)-fluoren 

Downstream Products

• 746-47-4 tetrabenzo[5.5]fulvalene 
• 1530-12-7 9,9'-bifluorenyl 
• 62-53-3 aniline 
• 31859-87-7 N-phenyl-9H-fluoren-9-amine 
• 71-43-2 benzene 
• 95820-74-9 biphenyl-4-yl-fluoren-9-yliden-amine 
• 5454-40-0 4-fluoren-9-ylidenamino-benzoic acid 
• 112045-64-4 (9-allyl-fluoren-9-yl)-phenyl-amine 
• 60253-51-2 1',1'-dioxo-3'-phenyl-1'λ⁶-spiro[fluorene-9,2'-thiazolidin]-4'-one 
• 39194-36-0 N-(9-methyl-9-fluorenyl)aniline 
• 39194-37-1 9-Methyl-9-methylanilinofluoren 
• 54930-60-8 3',3'-dimethyl-1'-phenylfluorene-9-spiro-2'-azetidin-4'-one 
• 119437-52-4 N-phenyl-9-butyl-9-aminofluorene 
• 119437-51-3 N-butyl-N-phenyl-9-aminofluorene 

Relevant articles and documents

Electrochemically Induced Chain Reactions: The Electrochemical Behavior of Nitrosobenzene in the Presence of Proton Donors in Tetrahydrofuran

The electrochemical reduction of nitrosobenzene in tetrahydrofuran with tetrabutylammonium hexafluorophosphate as the supporting electrolyte and in the presence of fluorene or indene at room temperature gives a mixture of an anil (1 or 3), a nitrone (2 or 4), and azoxybenzene and requires only a catalytic amount of electricity.Lowering the temperature and/or increasing the proportion of proton donor favors the formation of the anil at the expense of the nitrone and azoxybenzene: a 97percent yield of anil 1 was obtained from an electrolysis carried out at -30 deg C using 5 equiv of fluorene.The possible steps of the chain reactions involved are discussed on the basis of electrochemical and chemical data and digital simulation.With phenylacetylene as the proton donor, there is no reaction between nitrosobenzene and phenylacetylene and azoxybenzene is the main product formed.

Insights into the effect of ketylimine, aldimine, and vinylene group attachment and regiosubstitution on the fluorescence deactivation of fluorene

The spectroscopic and electrochemical properties of a 9-substituted fluorene ketylimine (3) were investigated and compared with those of its vinylene analogue (4) to determine the origins of the quenched fluorescence of these compounds. The predominate mo

Generation and characterization of the selenocysteinyl radical: Direct evidence from time-resolved UV/Vis, electron paramagnetic resonance, and fourier transform infrared spectroscopy

The selenocysteinyl radical 1 has been generated for the first time by laser flash photolysis (λexc = 266 nm) of dimethyl bis(N-tert-butoxycarbonyl)-L-selenocystine 2 and of [(9-fluorenylideneamino)- oxycarbonyl]methyl(N-tert-butoxycarbonyl)-L-selenocysteine 3 in acetonitrile and characterized by time-resolved (TR) UV/Vis, Fourier transform infrared (FTIR), and electron paramagnetic spectroscopy in combination with theoretical methods. A detailed product study was conducted using gas chromatography and one- and two-dimensional NMR spectroscopy. In the case of [(9-fluorenylideneamino) oxycarbonyl]methyl(N-tert-butoxycarbonyl)-L-selenocysteine 3, the (9-fluorenylideneamino)oxycarbonyl moiety serves as a photolabile protection group providing a caged selenocysteinyl radical suitable for biophysical applications. Cleavage of the diselenide bridge or the selenium-carbonyl bond by irradiation is possible in high quantum yields. Because of the lack of a good IR chromophore in the mid-IR region, the selenocysteinyl radical 1 cannot be monitored directly by TR FTIR spectroscopy. TR UV/Vis spectroscopy revealed the formation of the selenocysteinyl radical 1 from both precursors. The selenocysteinyl radical 1 has a lifetime τ ≈ 63 μs and exhibits a strong band located at λmax = 335 nm. Calculated UV absorptions of the selenocysteinyl radical (UB3LYP/6-311G(d,p)) are in good agreement with the experimental results. The use of TR UV/Vis spectroscopy permitted the determination of the decay rates of the selenocysteinyl radical in the presence of two quenchers. The product studies demonstrated the reversible photoreaction of dimethyl bis(N-tert-butoxycarbonyl) -L-selenocystine 2. Products of the photolysis of the caged selenocysteinyl radical precursor 3 are dimethyl bis(N-tert- butoxycarbonyl)-L-selenocystine 2, carbon dioxide, and some further smaller fragments. In addition, the photo-decomposition of the (9-fluorenylideneamino) oxycarbonyl moiety produced 9-fluorenone-oxime 4, 9-fluoren-imine 5, and 6 and 7 as products of the dimerization of two 9-fluorenoneiminoxy radicals 8.

Reaction of arynes with trifluoroacetylated β-diketones: Novel formation of isocoumarins and phenanthrenes

Polysubstituted isocoumarins were synthesized by the reaction of substituted 2-(trimethylsilyl)aryl triflates with trifluoromethylated β-diketones in the presence of CsF. The reaction proceeded through carbon-carbon bond insertion of aryne and intramolecular cyclization to form intermediates of alcohol anions, which extruded trifluoromethyl anion to afford isocoumarins. By using CuBr as a catalyst, 2 eq. of aryne reacted with β-diketones to afford phenanthrenes and 1,2-diarylethanones. Although reaction of 2-(trimethylsilyl)phenyl triflate with 1,1,1-trifluoro-4′-methylbenzoylacetone in the presence of CsF gave 3-(4′-methylphenyl)isocoumarin in 67% yield, addition of 0.2 eq. of CuCN resulted in the formation of 9-(4-methylbenzoyl)-10-trifluoromethylphenanthrene in 35% yield.

Selective, Oxophilic Imination of Ketones with Bis(dichloroaluminum) Phenylimide

Bis(dichloroaluminum) phenylimide, which can be readily prepared from ethylaluminum dichloride and aniline, is shown to be a highly selective iminating agent for aldehydes, ketones, and acid chlorides.Especially the transformation of α,β-unsaturated keton

Bildung von 1,2,4-Trithiolanen in Dreikomponenten-Gemischen aus Phenyl-azid, aromatischen Thioketonen und 2,2,4,4-Tetramethylcyclobutan-thionen: Eine Schwefel-Transfer-Reaktion unter Bildung von 'Thiocarbonyl-thiolaten' ((Alkylidensulfonio)thiolaten) als

The reaction of PhN3 and aromatic thioketones 18 (two-component reaction) at 80 degree yields only the corresponding imines 22, S, and N2.Under similar conditions, in the presence of sterically crowded 2,2,4,4-tetramethyl-cyclobutanethiones 19 (three-comp

Photoredox-Catalyzed Synthesis of α-Amino Acid Amides by Imine Carbamoylation

An operationally simple protocol for the photocatalytic carbamoylation of imines is reported. Easily available, bench-stable 4-amido Hantzsch ester derivatives serve as precursors to carbamoyl radicals that undergo rapid addition to N-aryl imines. The reaction proceeds under blue light irradiation in the presence of the photocatalyst 3DPAFIPN and Br?nsted/Lewis acid additives. Mechanistic studies indicated a photoredox mechanism that involves carbamoyl radicals.

Photoredox Radical/Polar Crossover Enables Construction of Saturated Nitrogen Heterocycles

Photoredox-mediated radical/polar crossover (RPC) processes offer new avenues for the synthesis of cyclic molecules. This process has been realized for the construction of medium-sized saturated nitrogen heterocycles. Photocatalytically generated alkyl ra

Preparation method of 10H-spiro[acridine-9,9'-fluorene] and derivative thereof

The invention provides a preparation method of 10H-spiro[acridine-9,9'-fluorene] and a derivative thereof, and belongs to the technical field of organic synthesis. According to the invention, an iminecompound, potassium fluoride, 18-corona-6 and methanesu

Photocatalytic and Chemoselective Transfer Hydrogenation of Diarylimines in Batch and Continuous Flow

A visible-light photocalytic method for the chemoselective transfer hydrogenation of imines in batch and continuous flow is described. The reaction utilizes Et3N as both hydrogen source and single-electron donor, enabling the selective reduction of imines derived from diarylketimines containing other reducible functional groups including nitriles, halides, esters, and ketones. The dual role of Et3N was confirmed by fluorescence quenching measurements, transient absorption spectroscopy, and deuterium-labeling studies. Continuous-flow processing facilitates straightforward scale-up of the reaction.