Production Method 1

2039-77-2

947-73-9

Reaction Conditions

1.1 Reagents: Ethyl N-[(phenylsulfonyl)oxy]ethanimidate Catalysts: p-Toluenesulfonic acid Solvents: Methanol ;  24 h, 23 °C
1.2 Reagents: Sodium bicarbonate Solvents: Water

Reference

Deacetylative Amination of Acetyl Arenes and Alkanes with C-C Bond Cleavage

Hyodo, Kengo ; Hasegawa, Genna; Maki, Hiroya; Uchida, Kingo, Organic Letters, 2019, 21(8), 2818-2822

Production Method 2

2097331-94-5

947-73-9

Reaction Conditions

1.1 Reagents: Chlorotrimethylsilane ,  Titanium isopropoxide ,  Magnesium Solvents: Tetrahydrofuran ;  4 h, 50 °C

Reference

Electrochemical oxidation induced intermolecular aromatic C-H imidation

Hu, Xia; Zhang, Guoting; Nie, Lei; Kong, Taige; Lei, Aiwen, Nature Communications, 2019, 10(1), 1-10

Production Method 3

573-17-1

947-73-9

Reaction Conditions

1.1 Reagents: Hydrochloric acid ,  Ammonia ,  Sodium amide Solvents: Diethyl ether

Reference

New route to 9-phenanthrylamine

Altiparmakian, R. H.; Braithwaite, Richard S. W., Journal of the Chemical Society [Section] C: Organic, 1967, (19),

Production Method 4

68572-87-2

947-73-9

Reaction Conditions

1.1 Reagents: Sodium hydroxide ,  Hydroxylamine-O-sulfonic acid Solvents: Acetonitrile ,  Water ;  16 h, rt

Reference

Transition-Metal-Free Access to Primary Anilines from Boronic Acids and a Common +NH2 Equivalent.

Voth, Samantha; Hollett, Joshua W.; McCubbin, J. Adam, Journal of Organic Chemistry, 2015, 80(5), 2545-2553

Production Method 5

19853-10-2

947-73-9

Reaction Conditions

1.1 Reagents: Sulfuric acid

Reference

A new cyclization reaction

Bradsher, Charles K.; Beavers, Dorothy J.; Little, Edwin D., Journal of the American Chemical Society, 1954, 76,

Production Method 6

60883-93-4

947-73-9

Reaction Conditions

1.1 Reagents: Lithium aluminum hydride

Reference

New synthetic route to 9,10-iminophenanthrene

Denis, J. N.; Krief, A., Tetrahedron, 1979, 35(24), 2901-3

Production Method 7

573-17-1

947-73-9

Reaction Conditions

1.1 Reagents: Sodium tert-butoxide ,  Ammonia Catalysts: [4-Methoxy-3,5,6-trimethyl-2′,4′,6′-tris(1-methylethyl)[1,1′-biphenyl]-2-yl]diph… ,  [5-Methoxy-3,4,6-trimethyl-2′,4′,6′-tris(1-methylethyl)[1,1′-biphenyl]-2-yl]diph… ,  [2′-(Amino-κN)[1,1′-biphenyl]-2-yl-κC](methanesulfonato-κO)[[5-methoxy-3,4,6-tri… Solvents: 1,4-Dioxane ;  rt; 24 h, 100 °C

Reference

Mild and Highly Selective Palladium-Catalyzed Monoarylation of Ammonia Enabled by the Use of Bulky Biarylphosphine Ligands and Palladacycle Precatalysts

Cheung, Chi Wai; Surry, David S.; Buchwald, Stephen L., Organic Letters, 2013, 15(14), 3734-3737

Production Method 8

947-73-9

Reaction Conditions

1.1 Reagents: Cesium carbonate ,  Benzophenone imine Catalysts: Bis(1,5-cyclooctadiene)nickel ,  1,2-Bis(dicyclohexylphosphino)ethane Solvents: Toluene ;  12 h, 100 °C; 100 °C → rt
1.2 Reagents: Hydrochloric acid Solvents: Tetrahydrofuran ,  Water ;  3 - 5 h, rt
1.3 Reagents: Potassium hydroxide Solvents: Water ;  pH 10 - 14
1.4 Reagents: Sodium borohydride Solvents: Methanol ;  rt

Reference

Nickel-Catalyzed Synthesis of Primary Aryl and Heteroaryl Amines via C-O Bond Cleavage

Yue, Huifeng; Guo, Lin; Liu, Xiangqian; Rueping, Magnus, Organic Letters, 2017, 19(7), 1788-1791

Production Method 9

573-17-1

947-73-9

Reaction Conditions

1.1 Reagents: Ammonia Catalysts: Copper oxide (Cu2O) Solvents: N-Methyl-2-pyrrolidone ,  Water ;  25 h, 110 °C

Reference

Material for organic electroluminescent device and organic electroluminescent device including the same

, United States, , ,

Production Method 10

573-17-1

947-73-9

Reaction Conditions

1.1 Reagents: Ammonia Catalysts: Copper oxide (Cu2O) Solvents: N-Methyl-2-pyrrolidone ;  25 h, 110 °C

Reference

Monoamine derivatives having dibenzothiophene structures and organic electroluminescence devices using them

, Japan, , ,

Production Method 11

109567-89-7

947-73-9

Reaction Conditions

1.1 Reagents: Dimethylbarbituric acid Catalysts: Tetrakis(triphenylphosphine)palladium Solvents: Dichloromethane

Reference

Efficient Synthesis of 9-Aminophenanthrenes and Heterocyclic Analogues by Electrocyclization of Biaryl Keteniminium Salts

Quinodoz, Pierre ; Kolleth, Amandine; Dagoneau, Dylan ; Yoshimura, Masahiko; Reyes Mendez, Lucia; et al, Helvetica Chimica Acta, 2022, 105(11),

Production Method 12

459410-52-7

947-73-9

Reaction Conditions

1.1 Reagents: Hydrochloric acid

Reference

Derivatives of phenanthrene. The preparation of 9-amino-, 9-iodo-, and 9-fluorophenanthrene

Goldberg, M. A.; Ordas, E. P.; Carsch, G., Journal of the American Chemical Society, 1947, 69, 260-2

Production Method 13

573-17-1

947-73-9

Reaction Conditions

1.1 Reagents: Cesium carbonate ,  Benzophenone imine Catalysts: Bis(dibenzylideneacetone)palladium ,  BINAP Solvents: Toluene ;  1 d, rt

Reference

Aryl amine derivative and application in organic electroluminescent device

, China, , ,

Production Method 14

573-17-1

947-73-9

Reaction Conditions

1.1 Reagents: Sodium ,  Ammonia Catalysts: Iron chloride (FeCl3) Solvents: Ammonia
1.2 180 min, -33 °C
1.3 Reagents: Ammonium nitrate

Reference

Synthesis of triaryls: hydroxy and amine dinaphthyl and diphenanthryl aryls by one-pot electron-transfer nucleophilic substitution reactions

Jimenez, Liliana B.; Torres, Natalia V.; Borioni, Jose L.; Pierini, Adriana B., Tetrahedron, 2014, 70(22), 3614-3620

Production Method 15

573-17-1

947-73-9

Reaction Conditions

1.1 Reagents: Sodium ,  Ammonia Catalysts: Iron chloride (FeCl3) Solvents: Ammonia ;  -33 °C
1.2 180 min, -33 °C
1.3 Reagents: Ammonium nitrate

Reference

A different route to the synthesis of 9,10-disubstituted phenanthrenes

Tempesti, Tomas C.; Pierini, Adriana B.; Baumgartner, Maria T., Journal of Organic Chemistry, 2005, 70(16), 6508-6511

Production Method 16

573-17-1

947-73-9

Reaction Conditions

1.1 Reagents: Ammonia Catalysts: Copper oxide (Cu2O) Solvents: N-Methyl-2-pyrrolidone ,  Water ;  25 h, 110 °C

Reference

Monoamine derivatives for use as hole transfer layers in organic electroluminescent devices

, United States, , ,

Production Method 17

573-17-1

947-73-9

Reaction Conditions

1.1 Reagents: Ammonia Catalysts: Copper oxide (Cu2O) Solvents: N-Methyl-2-pyrrolidone ,  Water ;  25 h, 110 °C

Reference

Mono amine derivatives and organic electroluminescent device including the same

, United States, , ,

Production Method 18

573-17-1

947-73-9

Reaction Conditions

1.1 Reagents: Copper oxide (Cu2O) ,  Ammonia Solvents: N-Methyl-2-pyrrolidone ,  Water ;  25 h, 110 °C

Reference

Materials for organic electroluminescent devices for improved emission life, and organic electroluminescent devices using the materials

, United States, , ,

Production Method 19

573-17-1

947-73-9

Reaction Conditions

1.1 Reagents: L-Hydroxyproline ,  Calcium carbonate ,  Ammonia ,  Cuprous iodide Solvents: Dimethyl sulfoxide ,  Water ;  100 °C; 2 h, 100 °C

Reference

Novel substituted heterocyclic compounds as electroluminescent host material for an organic electroluminescent device

, Korea, , ,

Production Method 20

68572-87-2

947-73-9

Reaction Conditions

1.1 Reagents: O-(2,4-Dinitrophenyl)hydroxylamine Solvents: Toluene ;  24 h, 50 °C

Reference

Elusive Metal-Free Primary Amination of Arylboronic Acids: Synthetic Studies and Mechanism by Density Functional Theory

Zhu, Chen; Li, Gongqiang; Ess, Daniel H.; Falck, John R.; Kurti, Laszlo, Journal of the American Chemical Society, 2012, 134(44), 18253-18256

9-Aminophenanthrene Raw materials

• 2-(1,1'-Biphenyl-2-yl)acetonitrile
• 1-(9-Phenanthrenyl)piperidine
• 9-Phenanthreneboronic Acid
• Phenanthrene, 9-azido-
• N-9-Phenanthrenyl-N-(phenylsulfonyl)benzenesulfonamide
• 9-Bromophenanthrene
• 9-Acetylphenanthrene

9-Aminophenanthrene Preparation Products

• 9-Aminophenanthrene (947-73-9)

• 1. Excess electrons in lithium–ethylamine solutions—density, electrical conductivity and EPR studies
  Phys. Chem. Chem. Phys., 1999,1, 3561-3565
• 2. Embedding cyclic nitrone in mesoporous silica particles for EPR spin trapping of superoxide and other radicals?
  Eric Besson,Stéphane Gastaldi,Emily Bloch,Selma Aslan,Hakim Karoui,Olivier Ouari,Micael Hardy Analyst, 2019,144, 4194-4203
• 3. Fatty acid positional distribution in colostrum and mature milk of women living in Inner Mongolia, North Jiangsu and Guangxi of China?
  Long Deng,Qian Zou,Biao Liu,Wenhui Ye,Chengfei Zhuo,Li Chen,Ze-Yuan Deng,Ya-Wei Fan,Jing Li Food Funct., 2018,9, 4234-4245
• 4. Emerging investigator series: kinetics of diopside reactivity for carbon mineralization in mafic–ultramafic rocks
  BrianaAguila,LandonHardee,H.ToddSchaef,SiavashZare,MohammadJavadAbdolhosseiniQomi,JarrodV.Crum,JadeE.HollimanJr.,ElenaTajueloRodriguez,LawrenceM.Anovitz,KevinM.Rosso,QuinR.S.Miller
• 5. Excimer–monomer switch: a reaction-based approach for selective detection of fluoride?
  Qiao Song,Angela Bamesberger,Lingyun Yang,Haley Houtwed,Haishi Cao Analyst, 2014,139, 3588-3592

Recent Advances in the Study of 9-Aminophenanthrene (CAS 947-73-9): Implications for Chemical Biology and Pharmaceutical Research

9-Aminophenanthrene (CAS 947-73-9) is a polycyclic aromatic amine that has garnered significant attention in recent years due to its potential applications in chemical biology and pharmaceutical research. This compound, characterized by its phenanthrene backbone and an amino group at the 9-position, exhibits unique photophysical and biochemical properties. Recent studies have explored its utility as a fluorescent probe, its interactions with biological macromolecules, and its potential as a scaffold for drug development. This research brief synthesizes the latest findings on 9-Aminophenanthrene, highlighting its mechanistic insights and translational potential.

A key area of investigation has been the photophysical properties of 9-Aminophenanthrene. A 2023 study published in the Journal of Physical Chemistry demonstrated that this compound exhibits strong fluorescence emission in the blue-green spectrum, making it a promising candidate for bioimaging applications. The study further elucidated the compound's solvatochromic behavior, which is attributed to intramolecular charge transfer (ICT) between the amino group and the phenanthrene ring. These findings suggest that 9-Aminophenanthrene could serve as a sensitive probe for monitoring microenvironmental changes in biological systems.

In the realm of drug discovery, researchers have explored the potential of 9-Aminophenanthrene as a pharmacophore. A recent Bioorganic & Medicinal Chemistry paper (2024) reported the synthesis of novel derivatives by modifying the amino group, resulting in compounds with enhanced binding affinity for DNA G-quadruplex structures. These derivatives showed selective cytotoxicity against cancer cell lines, particularly those with elevated telomerase activity. Molecular docking studies revealed that the planar structure of 9-Aminophenanthrene facilitates intercalation into G-quadruplex DNA, disrupting telomere maintenance in cancer cells.

The metabolic fate and toxicological profile of 9-Aminophenanthrene have also been subjects of recent investigation. A 2023 toxicokinetic study published in Chemical Research in Toxicology characterized the compound's hepatic metabolism, identifying cytochrome P450 1A2 as the primary enzyme responsible for its oxidation. The study also detected several hydroxylated metabolites, some of which exhibited increased genotoxic potential compared to the parent compound. These findings underscore the need for careful evaluation of 9-Aminophenanthrene derivatives in drug development pipelines.

From a synthetic chemistry perspective, novel methodologies for 9-Aminophenanthrene production have emerged. A 2024 Organic Letters publication described a palladium-catalyzed amination approach that significantly improves yield (82%) compared to traditional nitration-reduction routes. This advancement not only enhances the accessibility of 9-Aminophenanthrene for research purposes but also enables the preparation of isotopically labeled variants for mechanistic studies.

Looking forward, the unique properties of 9-Aminophenanthrene position it as a versatile tool in chemical biology and a promising scaffold for therapeutic development. Ongoing research is exploring its applications in super-resolution microscopy, targeted drug delivery systems, and as a molecular rotor for viscosity sensing in live cells. As our understanding of this compound deepens, it is likely to find increasing utility across multiple domains of biomedical research.

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