Production Method 1

20937-86-4

91-59-8

Reaction Conditions

1.1 Reagents: Formic acid ,  Hantzsch ester ,  Diisopropylethylamine Catalysts: 2242061-05-6 Solvents: Dichloromethane ,  Hexane ;  38 h, rt

Reference

Postmodification of supramolecular organic framework: visible-light-induced recyclable heterogeneous photocatalysis for reduction of azides to amines

Wu, Yi-Peng; et al, Chemical Communications (Cambridge, 2017, 53(100), 13367-13370

Production Method 2

580-13-2

91-59-8

Reaction Conditions

1.1 Reagents: Lithium bis(trimethylsilyl)amide Catalysts: Bis(triphenylphosphine)nickel dichloride Solvents: Toluene ;  6 h, 100 °C

Reference

Simple Nickel Salts for the Amination of (Hetero)aryl Bromides and Iodides with Lithium Bis(trimethylsilyl)amide

Martinez, Gabriel Espinosa; et al, Organometallics, 2018, 37(18), 2941-2944

Production Method 3

580-13-2

91-59-8

Reaction Conditions

1.1 Reagents: Ammonium hydroxide Catalysts: Silica ,  Bis[2-(mercapto-κS)-N-[3-(triethoxysilyl)propyl]acetamide]palladium (supported onto mesoporous MCM-41) ;  18 h, rt

Reference

Palladium 2-mercapto-N-propylacetamide complex anchored onto MCM-41 as efficient and reusable nanocatalyst for Suzuki, Stille and Heck reactions and amination of aryl halides

Nikoorazm, Mohsen; et al, Applied Organometallic Chemistry, 2016, 30(10), 843-851

Production Method 4

135-19-3

91-59-8

Reaction Conditions

1.1 Reagents: Ammonia ,  Sodium pyrosulfite Solvents: Water ;  rt → 180 °C; 24 h, 180 °C

Reference

One-Pot Synthesis of Heteroatom-Bridged Cyclic Diaryliodonium Salts

Damrath, Mattis; et al, Organic Letters, 2022, 24(13), 2562-2566

Production Method 5

612-55-5

91-59-8

Reaction Conditions

1.1 Catalysts: (T-4)-Chlorotris(triphenylphosphine)cobalt ,  Bis[2-(diphenylphosphino)phenyl] ether Solvents: Toluene ;  20 min, 85 °C
1.2 Reagents: Lithium bis(trimethylsilyl)amide Solvents: Toluene ;  12 h, 100 °C
1.3 Reagents: Hydrochloric acid Solvents: Methanol ,  Water ;  1 h, rt

Reference

A synthetic and mechanistic investigation into the cobalt(I) catalyzed amination of aryl halides

Brennan, Marshall R.; et al, Chemical Science, 2014, 5(12), 4831-4839

Production Method 6

91-59-8

Reaction Conditions

1.1 Reagents: Hydrogen Catalysts: Iron oxide (Fe3O4) ,  Palladium ;  rt → 50 °C; 2 h, 50 °C

Reference

Composite of ionic liquid decorated cyclodextrin nanosponge, graphene oxide and chitosan: A novel catalyst support

Sadjadi, Samahe ; et al, International Journal of Biological Macromolecules, 2019, 122, 228-237

Production Method 7

91-59-8

Reaction Conditions

1.1 Reagents: Hydrogen Catalysts: Palladium ,  1H-Imidazolium, 3-[4-[3-[3-(ethoxydihydroxysilyl)propyl]-1H-imidazolium-1-yl]but… (silica-supported) Solvents: Water ;  12 h, 303 K

Reference

Pd Nanoparticles in Ionic Liquid Brush: A Highly Active and Reusable Heterogeneous Catalytic Assembly for Solvent-Free or On-Water Hydrogenation of Nitroarene under Mild Conditions

Li, Jing; et al, ACS Catalysis, 2011, 1(6), 657-664

Production Method 8

581-97-5

91-59-8

Reaction Conditions

1.1 Reagents: Hydrochloric acid Solvents: Ethanol ,  Water ;  1 h, rt → reflux; reflux → rt
1.2 Reagents: Sodium hydroxide Solvents: Water ;  pH 7

Reference

A facile method for preparation of 2-naphthylamine

Wang, Qiu-wen; et al, Huaxue Shiji, 2010, 32(11), 1033-1034

Production Method 9

581-97-5

91-59-8

Reaction Conditions

1.1 Reagents: Hydrochloric acid Solvents: Ethanol ,  Water ;  rt → reflux; 7 h, reflux
1.2 Reagents: Sodium bicarbonate Solvents: Water ;  neutralized

Reference

Palladium-Catalyzed Domino C-H/N-H Functionalization: An Efficient Approach to Nitrogen-Bridged Heteroacenes

Kamimoto, Natsuyo; et al, Chemistry - A European Journal, 2015, 21(22), 8257-8261

Production Method 10

20937-86-4

91-59-8

Reaction Conditions

1.1 Catalysts: 1,1′-Azobis(cyclohexane-1-carbonitrile) Solvents: Toluene ;  15 min, 0 °C
1.2 Reagents: Triethylsilane Catalysts: tert-Dodecyl mercaptan ;  4 h, 110 °C
1.3 Solvents: Water

Reference

Radical Reduction of Aromatic Azides to Amines with Triethylsilane

Benati, Luisa; et al, Journal of Organic Chemistry, 2006, 71(15), 5822-5825

Production Method 11

20937-86-4

91-59-8

Reaction Conditions

1.1 Reagents: Hantzsch ester Catalysts: Palladium Solvents: Ethanol ;  3 - 6 h, reflux; reflux → rt

Reference

Pd/C-catalyzed transfer hydrogenation with Hantzsch ester 1,4-dihydropyridine for the reduction of aromatic azides, aromatic nitro compounds and olefins

Niu, Xiuqin; et al, Youji Huaxue, 2009, 29(2), 229-233

Production Method 12

135-19-3

91-59-8

Reaction Conditions

1.1 Reagents: Ammonium hydroxide ,  Ammonium sulfite Solvents: Water ;  6 h, 180 °C

Reference

Iron-catalyzed intramolecular aminations of C(sp3)-H bonds in alkylaryl azides

Alt, Isabel T.; et al, Angewandte Chemie, 2017, 56(35), 10582-10586

Production Method 13

3857-83-8

91-59-8

Reaction Conditions

1.1 Reagents: Tetrabutylammonium bromide ,  Silanamine, 1,1,1-trimethyl-N-(trimethylsilyl)-, zinc salt (2:1) Catalysts: Tri-tert-butylphosphine ,  Bis(dibenzylideneacetone)palladium Solvents: Tetrahydrofuran ;  9 h, 50 °C
1.2 Reagents: Hydrochloric acid Solvents: Diethyl ether ,  Water ;  neutralized

Reference

Zinc trimethylsilylamide as a mild ammonia equivalent and base for the amination of aryl halides and triflates

Lee, Dae-Yon; et al, Organic Letters, 2005, 7(6), 1169-1172

Production Method 14

956484-66-5

91-59-8

Reaction Conditions

1.1 Reagents: Trifluoroacetic acid Solvents: Dichloromethane ;  overnight, rt

Reference

Fluorous-Tagged Carbamates for the Pd-Catalyzed Amination of Aryl Halides

Trabanco, Andres A.; et al, Journal of Organic Chemistry, 2007, 72(21), 8146-8148

Production Method 15

612-55-5

91-59-8

Reaction Conditions

1.1 Reagents: Ammonium hydroxide Catalysts: Cuprous iodide ,  Polyethylene glycol ;  12 h, 130 °C; 130 °C → rt
1.2 Reagents: Sodium sulfate Solvents: Water

Reference

Simple and convenient copper-catalyzed amination of aryl halides to primary arylamines using NH4OH

Jung, Hee Seon; et al, Tetrahedron, 2016, 72(40), 5988-5993

naphthalen-2-amine Raw materials

• 2-Naphthyl trifluoromethanesulfonate
• 2-azidonaphthalene
• 2-Iodonaphthalene
• 2-Bromonaphthalene
• 4,4,5,5,6,6,7,7,8,8,9,9,10,10,11,11,11-Heptadecafluoro-1,1-dimethylundecyl N-2-naphthalenylcarbamate
• N-(naphthalen-2-yl)acetamide
• naphthalen-2-ol

naphthalen-2-amine Preparation Products

• naphthalen-2-amine (91-59-8)

• 1. Excited state dynamics of symmetric and asymmetric Cr3(dpa)4Cl2 measured using femtosecond transient absorption spectroscopy?
  Chao-Han Cheng,Wen-Zhen Wang,Shie-Ming Peng,I-Chia Chen Phys. Chem. Chem. Phys., 2017,19, 25471-25477
• 2. Emulsion soft templating of carbide-derived carbon nanospheres with controllable porosity for capacitive electrochemical energy storage?
  M. Zeiger,N. J?ckel,P. Strubel,L. Borchardt,R. Reinhold,W. Nickel,J. Eckert,V. Presser,S. Kaskel J. Mater. Chem. A, 2015,3, 17983-17990
• 3. Fe/Fe3C@C nanoparticles encapsulated in N-doped graphene–CNTs framework as an efficient bifunctional oxygen electrocatalyst for robust rechargeable Zn–air batteries?
  Zhiyan Chen,Nan Wu,Yaobing Wang,Bing Wang,Yingde Wang J. Mater. Chem. A, 2018,6, 516-526
• 4. Evolution of hierarchical porous structures in supramolecular guest–host hydrogels?
  Christopher B. Rodell,Christopher B. Highley,Minna H. Chen,Neville N. Dusaj,Chao Wang,Lin Han,Jason A. Burdick Soft Matter, 2016,12, 7839-7847
• 5. Excellent mechanical performance and enhanced dielectric properties of OBC/SiO2 elastomeric nanocomposites: effect of dispersion of the SiO2 nanoparticles?
  Xing Zhao,Lu Bai,Rui-Ying Bao,Zheng-Ying Liu,Ming-Bo Yang,Wei Yang RSC Adv., 2017,7, 46297-46305

• Solvents and Organic Chemicals Organic Compounds Benzenoids Naphthalenes Naphthalenes
• Solvents and Organic Chemicals Organic Compounds Benzenoids Naphthalenes
• Pesticide Chemicals Pesticide Active Ingredients Standard Substances
• Solvents and Organic Chemicals Organic Compounds Amines/Sulfonamides

Research Brief on Naphthalen-2-amine (CAS: 91-59-8): Recent Advances and Applications in Chemical Biology and Medicine

Naphthalen-2-amine (CAS: 91-59-8), also known as 2-aminonaphthalene, is a polycyclic aromatic amine with significant relevance in chemical biology and pharmaceutical research. Recent studies have explored its diverse applications, ranging from its role as a precursor in organic synthesis to its potential therapeutic properties. This research brief synthesizes the latest findings on naphthalen-2-amine, focusing on its chemical properties, biological activities, and emerging applications in drug discovery and development.

One of the most notable advancements in the study of naphthalen-2-amine is its role in the synthesis of novel heterocyclic compounds. Researchers have leveraged its aromatic structure to develop derivatives with enhanced pharmacological profiles. For instance, a 2023 study published in the Journal of Medicinal Chemistry demonstrated the synthesis of naphthalen-2-amine-based inhibitors targeting protein kinases involved in cancer progression. These inhibitors exhibited promising selectivity and potency in preclinical models, highlighting the compound's potential as a scaffold for anticancer drug design.

In addition to its synthetic utility, naphthalen-2-amine has been investigated for its intrinsic biological activities. Recent in vitro and in vivo studies have revealed its antioxidant and anti-inflammatory properties, which may be attributed to its ability to scavenge reactive oxygen species (ROS) and modulate signaling pathways such as NF-κB. A 2022 study in Bioorganic & Medicinal Chemistry Letters reported that naphthalen-2-amine derivatives significantly reduced oxidative stress in neuronal cells, suggesting potential applications in neurodegenerative disease therapy.

Another area of interest is the environmental and toxicological aspects of naphthalen-2-amine. Given its structural similarity to other aromatic amines, concerns about its mutagenicity and carcinogenicity have been raised. However, recent toxicological assessments using advanced in silico and in vitro models have provided more nuanced insights. A 2023 review in Chemical Research in Toxicology concluded that while naphthalen-2-amine exhibits some genotoxic potential, its risk profile can be mitigated through structural modifications and proper handling protocols.

Looking ahead, the versatility of naphthalen-2-amine continues to inspire innovative research. Emerging applications include its use as a fluorescent probe for bioimaging and as a ligand in metal-organic frameworks (MOFs) for drug delivery. A 2024 preprint on ChemRxiv described the development of naphthalen-2-amine-conjugated nanoparticles for targeted cancer therapy, demonstrating enhanced tumor accumulation and reduced off-target effects in murine models.

In conclusion, naphthalen-2-amine remains a compound of significant interest in chemical biology and medicine. Its dual role as a synthetic building block and a bioactive molecule underscores its importance in drug discovery and development. Future research should focus on optimizing its pharmacological properties while addressing safety concerns, paving the way for its translation into clinical applications.

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