Production Method 1

90-30-2

Reaction Conditions

1.1 Reagents: Lithium bis(trimethylsilyl)amide Catalysts: (SP-4-4)-[2′-(Amino-κN)[1,1′-biphenyl]-2-yl-κC][4-(diphenylphosphino-κP)-6-(diph… Solvents: 1,2-Dimethoxyethane ;  48 h, 80 °C; 80 °C → rt
1.2 Solvents: Water ;  rt

Reference

NIXANTPHOS: a highly active ligand for palladium catalyzed Buchwald-Hartwig amination of unactivated aryl chlorides

Mao, Jianyou; Zhang, Jiadi; Zhang, Shuguang; Walsh, Patrick J., Dalton Transactions, 2018, 47(26), 8690-8696

Production Method 2

98-80-6

90-30-2

Reaction Conditions

1.1 Reagents: Triethylamine Catalysts: 2000229-99-0 Solvents: Ethanol ;  5 h, 25 °C

Reference

Copper complexes of 1,4-diazabutadiene ligands: Tuning of metal oxidation state and, application in catalytic C-C and C-N bond formation

Mukherjee, Aparajita; Basu, Semanti; Bhattacharya, Samaresh, Inorganica Chimica Acta, 2020, 500,

Production Method 3

90-11-9

90-30-2

Reaction Conditions

1.1 Reagents: Sodium tert-butoxide Catalysts: 2299268-90-7 ;  24 h, 110 °C

Reference

Mixed er-NHC/phosphine Pd(II) complexes and their catalytic activity in the Buchwald-Hartwig reaction under solvent-free conditions

Ageshina, Alexandra A.; Sterligov, Grigorii K.; Rzhevskiy, Sergey A.; Topchiy, Maxim A.; Chesnokov, Gleb A.; et al, Dalton Transactions, 2019, 48(10), 3447-3452

Production Method 4

86-53-3

90-30-2

Reaction Conditions

1.1 Reagents: Potassium bis(trimethylsilyl)amide Catalysts: (T-4)-[1,1′-Bis(diphenylphosphino-κP)ferrocene]dichloronickel Solvents: Toluene ;  2 min, rt; 6 h, 140 °C; cooled
1.2 Solvents: Water

Reference

Nickel-Catalyzed Amination of Aryl Nitriles for Accessing Diarylamines through C-CN Bond Activation

Wu, Ke; Rong, Qiang; Sun, Nan; Hu, Baoxiang; Shen, Zhenlu; et al, Advanced Synthesis & Catalysis, 2021, 363(20), 4708-4713

Production Method 5

622-37-7

90-30-2

Reaction Conditions

1.1 Reagents: Trifluoromethanesulfonic acid Solvents: Dichloromethane

Reference

Synthetic methods and reactions. 188. Triflic acid catalyzed phenylamination of aromatics with phenyl azide

Olah, George A.; Ramaiah, Pichika; Wang, Qi; Prakash, G. K. Surya, Journal of Organic Chemistry, 1993, 58(24), 6900-1

Production Method 6

100-68-5

90-30-2

Reaction Conditions

1.1 Reagents: Sodium bis(trimethylsilyl)amide Catalysts: Bis(1,5-cyclooctadiene)nickel ,  1,2-Bis(dicyclohexylphosphino)ethane Solvents: Toluene ;  12 h, 100 °C

Reference

Nickel-catalyzed Amination of Aryl Thioethers: A Combined Synthetic and Mechanistic Study

Bismuto, Alessandro ; Delcaillau, Tristan; Muller, Patrick; Morandi, Bill, ACS Catalysis, 2020, 10(8), 4630-4639

Production Method 7

90-30-2

Reaction Conditions

1.1 Catalysts: p-Toluenesulfonic acid Solvents: 1,2-Dichloroethane ;  rt; 24 h, 80 °C; 80 °C → rt
1.2 Solvents: Water ;  rt

Reference

Diels-Alder cycloadditions of N-arylpyrroles via aryne intermediates using diaryliodonium salts

Chen, Huangguan; Han, Jianwei ; Wang, Limin, Beilstein Journal of Organic Chemistry, 2018, 14, 354-363

Production Method 8

90-30-2

Reaction Conditions

1.1 Reagents: Tripotassium phosphate Catalysts: Palladium acetylacetonate ,  Imidazo[1,5-a]pyridinium, 2-(2,6-diethyl-4-methylphenyl)-5-[2,4,6-tris(1-methyle… Solvents: 1,4-Dioxane ;  30 min, rt; 24 h, 130 °C

Reference

Well-Designed N-Heterocyclic Carbene Ligands for Palladium-Catalyzed Denitrative C-N Coupling of Nitroarenes with Amines

Chen, Wei; Chen, Kai; Chen, Wanzhi ; Liu, Miaochang ; Wu, Huayue, ACS Catalysis, 2019, 9(9), 8110-8115

Production Method 9

90-30-2

Reaction Conditions

1.1 Reagents: Sodium tert-butoxide Catalysts: Stereoisomer of [1,3-bis[2,6-bis(1-methylethyl)phenyl]tetrahydro-2(1H)-pyrimidin… ;  12 h, 110 °C

Reference

Solvent-Free Buchwald-Hartwig (Hetero)arylation of Anilines, Diarylamines, and Dialkylamines Mediated by Expanded-Ring N-Heterocyclic Carbene Palladium Complexes

Topchiy, Maxim A.; Dzhevakov, Pavel B.; Rubina, Margarita S.; Morozov, Oleg S.; Asachenko, Andrey F.; et al, European Journal of Organic Chemistry, 2016, 2016(10), 1908-1914

Production Method 10

90-30-2

Reaction Conditions

1.1 Reagents: Sodium tert-butoxide Catalysts: 1,1-Bis(diphenylphosphino)ferrocene ,  (T-4)-[1,1′-Bis(diphenylphosphino-κP)ferrocene]bis(triphenyl phosphite-κP)nickel Solvents: Toluene ;  18 h, 100 °C; cooled
1.2 Reagents: Hydrogen peroxide Solvents: Water ;  2 h, cooled

Reference

Stable nickel(0) phosphites as catalysts for C-N cross-coupling reactions

Kampmann, Sven S.; Sobolev, Alexandre N.; Koutsantonis, George A.; Stewart, Scott G., Advanced Synthesis & Catalysis, 2014, 356(9), 1967-1973

Production Method 11

1144-13-4

90-30-2

Reaction Conditions

1.1 Reagents: Sodium tert-butoxide Catalysts: 2584981-19-9 Solvents: tert-Butanol ,  Water ;  18 h, 110 °C

Reference

Broad-Scope Amination of Aryl Sulfamates Catalyzed by a Palladium Phosphine Complex

Monti, Andrea ; Lopez-Serrano, Joaquin; Prieto, Auxiliadora; Nicasio, M. Carmen, ACS Catalysis, 2023, 13(16), 10945-10952

Production Method 12

90-30-2

Reaction Conditions

1.1 Reagents: Potassium carbonate ,  Tetrabutylammonium bromide Catalysts: Palladium diacetate ,  2,6-Bis(diphenylphosphino)pyridine Solvents: Dimethylacetamide ;  3 h, 135 °C; 135 °C → rt
1.2 Reagents: Water ;  rt

Reference

2,6-Bis(diphenylphosphino)pyridine: a simple ligand showing high performance in palladium-catalyzed C-N coupling reactions

Nadri, Shirin; Rafiee, Ezzat; Jamali, Sirous; Joshaghani, Mohammad, Tetrahedron Letters, 2014, 55(30), 4098-4101

Production Method 13

90-11-9

90-30-2

Reaction Conditions

1.1 Reagents: Sodium tert-butoxide Catalysts: Palladium diacetate ,  1H-Imidazolium, 1,3-bis[2,6-bis(1-methylethyl)phenyl]-2-[(dicyclohexylphosphino)… Solvents: 1,4-Dioxane ;  10 min, 120 °C

Reference

Recyclable Catalysts for Palladium-Catalyzed Aminations of Aryl Halides

Dumrath, Andreas; Luebbe, Christa; Neumann, Helfried; Jackstell, Ralf; Beller, Matthias, Chemistry - A European Journal, 2011, 17(35), 9599-9604

Production Method 14

130-14-3

1865-45-8

90-30-2

Reaction Conditions

Reference

Reaction of sodium salts of aromatic sulfonic acids with alkali metal arylides

Shein, S. M.; Rusov, V. P.; Sokolenko, V. I., Zhurnal Organicheskoi Khimii, 1980, 16(11), 2356-8

Production Method 15

130-14-3

1865-45-8

90-30-2

Reaction Conditions

Reference

Replacement of an aromatically bound sulfo group with an arylamino group

Shein, S. M.; Rusov, V. P.; Sokolenko, V. I., Zhurnal Organicheskoi Khimii, 1979, 15(11), 2426-7

Production Method 16

90-11-9

90-30-2

Reaction Conditions

1.1 Reagents: Cesium carbonate Catalysts: Palladium diacetate ,  BINAP Solvents: Toluene ;  12 h, 110 °C

Reference

A wearable AIEgen-based lateral flow test strip for rapid detection of SARS-CoV-2 RBD protein and N protein

Zhang, Guo-Qiang; Gao, Zhiyuan; Zhang, Jingtian; Ou, Hanlin; Gao, Heqi; et al, Cell Reports Physical Science, 2022, 3(2),

Production Method 17

98-80-6

90-30-2

Reaction Conditions

1.1 Reagents: Potassium carbonate Catalysts: Iron ,  Palladium Solvents: Water ;  5 h, rt

Reference

Facile synthesis of Fe@Pd nanowires and their catalytic activity in ligand-free C-N bond formation in water

Nasrollahzadeh, Mahmoud; Azarian, Abbas; Ehsani, Ali; Zahraei, Ali, Tetrahedron Letters, 2014, 55(17), 2813-2817

Production Method 18

90-11-9

90-30-2

Reaction Conditions

1.1 Reagents: Sodium tert-butoxide Catalysts: 2882827-29-2 Solvents: Toluene ;  1 h, 22 °C

Reference

Amines as Activating Ligands for Phosphine Palladium(II) Precatalysts: Effect of Amine Ligand Identity on the Catalyst Efficiency

Pierce, Jordan K.; Hiatt, Lindsey D.; Howard, James R.; Hu, Huaiyuan; Qu, Fengrui ; et al, Organometallics, 2022, 41(24), 3861-3871

N-Phenyl-1-napthyl Amine Raw materials

• Sodium naphthalene-1-sulfonate
• Phenylboronic acid
• Thioanisol
• Benzenamine, monosodium salt
• 1-Cyanonaphthalene
• Sulfamic acid, N,N-dimethyl-, 1-naphthalenyl ester
• azidobenzene
• 1-Bromonaphthalene

N-Phenyl-1-napthyl Amine Preparation Products

• N-Phenyl-1-napthyl Amine (90-30-2)

• 1. Excimer and exciplex formation in a pair of bright phosphorescent isomers constructed from Cu3(pyrazolate)3 and Cu3I3 coordination luminophores?
  Shun-Ze Zhan,Mian Li,Xiao-Ping Zhou,Dan Li,Seik Weng Ng RSC Adv., 2011,1, 1457-1459
• 2. Excellent peroxidase mimicking property of CuO/Pt nanocomposites and their application as an ascorbic acid sensor?
  Xinhuan Wang,Shuangfei Cai,Cui Qi Analyst, 2017,142, 2500-2506
• 3. Etching of glass microchips with supercritical water?
  Pavel Karásek,Jakub Grym,Michal Roth,Josef Planeta,Franti?ek Foret Lab Chip, 2015,15, 311-318
• 4. Excimer emission and magnetoluminescence of radical-based zinc(ii) complexes doped in host crystals?
  Shojiro Kimura,Tetsuro Kusamoto Chem. Commun., 2020,56, 11195-11198
• 5. 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

• Solvents and Organic Chemicals Organic Compounds Benzenoids Naphthalenes Naphthalenes
• Solvents and Organic Chemicals Organic Compounds Benzenoids Naphthalenes
• Solvents and Organic Chemicals Organic Compounds Amines/Sulfonamides

N-Phenyl-1-naphthyl amine: A Comprehensive Overview

N-Phenyl-1-naphthyl amine, also known by its CAS number CAS No. 90-30-2, is a versatile organic compound with significant applications in various fields of chemistry and materials science. This compound, characterized by its unique structure combining a phenyl group and a naphthyl moiety, has garnered attention due to its electronic properties and potential uses in advanced materials. Recent studies have further elucidated its role in modern chemical research, particularly in the development of novel materials for electronic devices and pharmaceuticals.

The molecular structure of N-Phenyl-1-naphthyl amine consists of a naphthalene ring system substituted with an amino group (-NH2) at the 1-position, which is further connected to a phenyl group via an N atom. This arrangement imparts the compound with distinct electronic characteristics, making it suitable for applications in organic electronics. Researchers have explored its ability to act as a building block for constructing π-conjugated systems, which are crucial for materials exhibiting semiconducting properties.

Recent advancements in materials science have highlighted the potential of N-Phenyl-1-naphthyl amine as a precursor for synthesizing organic semiconductors. These materials are increasingly being used in thin-film transistors (TFTs) and organic light-emitting diodes (OLEDs), where their electronic properties play a pivotal role in device performance. Studies published in leading journals such as Advanced Materials and Nature Electronics have demonstrated how the compound's structure can be tailored to enhance charge transport properties, thereby improving device efficiency.

In addition to its role in electronics, N-Phenyl-1-naphthyl amine has found applications in pharmaceutical chemistry. Its ability to form stable complexes with metal ions has made it a valuable ligand in coordination chemistry. Recent research has focused on its use as a chelating agent in drug delivery systems, where it can bind to metal ions such as copper or zinc, enhancing the bioavailability of therapeutic agents.

The synthesis of CAS No. 90-30-2 involves a multi-step process that typically begins with the preparation of 1-naphthylamine, followed by nucleophilic substitution with phenyl groups under controlled conditions. Optimization of reaction conditions has been a focus of recent studies, with researchers exploring greener synthesis methods that minimize environmental impact while maintaining high yields.

From an environmental standpoint, understanding the fate and transport of N-Phenyl-1-naphthyl amine in natural systems is crucial for assessing its ecological impact. Recent toxicological studies have evaluated its biodegradability and potential toxicity to aquatic organisms, providing insights into its safe handling and disposal.

In conclusion, N-Phenyl-1-naphthyl amine, or CAS No. 90-30-2, stands as a testament to the ingenuity of modern chemical research. Its diverse applications across electronics, pharmaceuticals, and materials science underscore its importance as a versatile compound. As research continues to uncover new facets of its properties and potential uses, this compound is poised to play an even greater role in shaping future technological advancements.

• 3920-79-4(9-Phenanthrenamine, N-phenyl-)
• 498572-37-5(9-Phenanthrenamine, N-1-naphthalenyl-)
• 101228-53-9(9-Anthracenamine, N-1-naphthalenyl-)
• 28258-64-2(Naphthalenamine,N-phenyl-)
• 2233-88-7(9,10-Anthracenediamine,N9,N10-diphenyl-)
• 65838-93-9(1-Pyrenamine, N-phenyl-)
• 4669-06-1(N-naphthalen-1-ylnaphthalen-2-amine)
• 98683-00-2(N-Phenyl-1-anthraMine)
• 79227-35-3(1,4-Naphthalenediamine, N-1-naphthalenyl-)
• 737-89-3(1,1'-Dinaphthylamine)