Production Method 1

85-81-4

90-52-8

Reaction Conditions

1.1 Reagents: Hydrochloric acid ,  Stannous chloride Solvents: Water ;  4 h, rt
1.2 Reagents: Sodium hydroxide Solvents: Water ;  30 min, neutralized, rt

Reference

Primacenes: Novel non-cytotoxic primaquine-ferrocene conjugates with anti-Pneumocystis carinii activity

Matos, Joana; Vale, Nuno; Collins, Margaret S.; Gut, Jiri; Rosenthal, Philip J.; et al, MedChemComm, 2010, 1(3), 199-201

Production Method 2

63457-03-4

90-52-8

Reaction Conditions

1.1 Reagents: Hydrogen Catalysts: Palladium Solvents: Ethanol ;  1 h, 25 °C

Reference

Synthesis and biological evaluation of benzhydryl-based antiplasmodial agents possessing Plasmodium falciparum chloroquine resistance transporter (PfCRT) inhibitory activity

Relitti, Nicola ; Federico, Stefano ; Pozzetti, Luca ; Butini, Stefania ; Lamponi, Stefania ; et al, European Journal of Medicinal Chemistry, 2021, 215,

Production Method 3

85-81-4

90-52-8

Reaction Conditions

1.1 Reagents: Carbon ,  Hydrazine hydrate (1:1) Catalysts: Iron chloride (FeCl3) Solvents: Methanol ;  12 h, 80 °C

Reference

Uncatalyzed, on water oxygenative cleavage of inert C-N bond with concomitant 8,7-amino shift in 8-aminoquinoline derivatives

Botla, Vinayak; Pilli, NavyaSree; Malapaka, Chandrasekharam, Green Chemistry, 2019, 21(7), 1735-1742

Production Method 4

85-81-4

90-52-8

Reaction Conditions

1.1 Reagents: Stannous chloride Solvents: Ethanol ;  1 h, reflux; reflux → rt
1.2 Reagents: Sodium hydroxide Solvents: Ethyl acetate ,  Water ;  pH 11, rt

Reference

Systematic ligand variation to modulate the electrochemical properties of iron and manganese complexes

Rohner, Stefan S.; Kinzel, Niklas W.; Werle, Christophe; Leitner, Walter, Dalton Transactions, 2019, 48(35), 13205-13211

Production Method 5

85-81-4

90-52-8

Reaction Conditions

1.1 Reagents: Hydrogen Catalysts: Palladium Solvents: Methanol ,  Dichloromethane ;  48 h, rt

Reference

Influence of Functionalized Substituents on the Electron-Transfer Abilities of Copper Guanidinoquinoline Complexes

Stanek, Julia; Konrad, Marc; Mannsperger, Johannes; Hoffmann, Alexander; Herres-Pawlis, Sonja, European Journal of Inorganic Chemistry, 2018, 2018(46), 4997-5006

Production Method 6

85-81-4

90-52-8

Reaction Conditions

1.1 Reagents: Hydrogen Catalysts: Nickel Solvents: Ethanol ;  45 min, 45 psi, rt

Reference

Ring-substituted quinolines as potential anti-tuberculosis agents

Vangapandu, Suryanarayana; Jain, Meenakshi; Jain, Rahul; Kaur, Sukhraj; Singh, Prati Pal, Bioorganic & Medicinal Chemistry, 2004, 12(10), 2501-2508

Production Method 7

85-81-4

90-52-8

Reaction Conditions

1.1 Reagents: Hydrogen Catalysts: Palladium Solvents: Methanol ;  rt; 24 h, rt

Reference

Novel squaramides with in vitro liver stage antiplasmodial activity

Ribeiro, Carlos J. A.; Espadinha, Margarida; Machado, Marta; Gut, Jiri; Goncalves, Lidia M.; et al, Bioorganic & Medicinal Chemistry, 2016, 24(8), 1786-1792

Production Method 8

90-52-8

Reaction Conditions

1.1 Reagents: Hydrochloric acid Solvents: Ethanol

Reference

Transition metal free oxygenation of 8-aminoquinoline amides in water

Yao, Xinghui; Weng, Xin; Wang, Kaixuan; Xiang, Haifeng; Zhou, Xiangge, Green Chemistry, 2018, 20(11), 2472-2476

Production Method 9

85-81-4

90-52-8

Reaction Conditions

1.1 Solvents: Water

Reference

Reduction of heteroaromatic nitro compounds with baker's yeast

Takeshita, Mitsuhiro; Yoshida, Sachiko, Heterocycles, 1990, 31(12), 2201-4

Production Method 10

85-81-4

90-52-8

Reaction Conditions

1.1 Reagents: L-Ascorbic acid Catalysts: Tris(2,2′-bipyridyl)ruthenium(II) chloride Solvents: Methanol ,  Water ;  5 h, rt
1.2 Reagents: Triethylamine ;  rt

Reference

Visible-light-photocatalyzed reductions of N-heterocyclic nitroaryls to anilines utilizing ascorbic acid reductant

Todorov, Aleksandar R.; Aikonen, Santeri ; Muuronen, Mikko ; Helaja, Juho, Organic Letters, 2019, 21(10), 3764-3768

Production Method 11

85-81-4

90-52-8

Reaction Conditions

1.1 Reagents: Carbon ,  Hydrazine hydrate (1:1) Catalysts: Iron chloride (FeCl3) Solvents: Methanol ;  12 h, 80 °C

Reference

Visible Light-Promoted Photocatalytic C-5 Carboxylation of 8-Aminoquinoline Amides and Sulfonamides via a Single Electron Transfer Pathway

Sen, Chiranjit; Sahoo, Tapan; Singh, Harshvardhan; Suresh, Eringathodi ; Ghosh, Subhash Chandra, Journal of Organic Chemistry, 2019, 84(16), 9869-9896

Production Method 12

85-81-4

90-52-8

Reaction Conditions

1.1 Reagents: Iron chloride (FeCl3) ,  Hydrazine hydrate (1:1) Solvents: Methanol ;  12 h, 80 °C

Reference

5-Position-selective C-H trifluoromethylation of 8-aminoquinoline derivatives

Kuninobu, Yoichiro; Nishi, Mitsumi; Kanai, Motomu, Organic & Biomolecular Chemistry, 2016, 14(34), 8092-8100

Production Method 13

85-81-4

90-52-8

Reaction Conditions

1.1 Reagents: Hydrogen Catalysts: Palladium (MOF-74(Zn)-supported) ,  Titanium, hexakis[μ-[1,4-benzenedicarboxylato(2-)-κO1:κO′1]]tetra-μ-hydroxyocta-… Solvents: Water ;  12 h, 1 atm, rt

Reference

The selective hydrogenation of nitroarenes and alkenes catalyzed by Pd@MOFs: The role of electronic interactions between Pd nanoparticles and MOFs on the reaction

Xu, Jiaxian; Chen, Fei; Xu, Xuran; Lu, Guo-Ping, Molecular Catalysis, 2020, 495,

Production Method 14

85-81-4

90-52-8

Reaction Conditions

1.1 Reagents: Phenylsilane Catalysts: Dicobalt octacarbonyl Solvents: Tetrahydrofuran ;  3 h, 100 °C

Reference

Cobalt catalyzed chemoselective reduction of nitroarenes: hydrosilylation under thermal and photochemical reaction conditions

Panda, Surajit; Nanda, Amareshwar; Behera, Rakesh R.; Ghosh, Rahul; Bagh, Bidraha, Chemical Communications (Cambridge, 2023, 59(30), 4527-4530

Production Method 15

90-34-6

90-52-8

Reaction Conditions

1.1 Reagents: Piperidine Catalysts: (OC-6-14)-[[2,3-Butanedione 2,3-di(oximato-κN)](1-)][2,3-butanedione 2,3-di(oxim… ,  Iridium(1+), [4,4′-bis(1,1-dimethylethyl)-2,2′-bipyridine-κN1,κN1′]bis[2-(2-pyri… Solvents: Acetonitrile ;  rt → -78 °C; 72 h, -78 °C

Reference

Minimization of Back-Electron Transfer Enables the Elusive sp3 C-H Functionalization of Secondary Anilines

Zhao, Huaibo; Leonori, Daniele, Angewandte Chemie, 2021, 60(14), 7669-7674

6-methoxyquinolin-8-amine Raw materials

• 6-Methoxy-8-nitroquinoline
• Primaquine
• 4-chloro-6-methoxy-8-nitroquinoline

6-methoxyquinolin-8-amine Preparation Products

• 6-methoxyquinolin-8-amine (90-52-8)

• 1. An amino group functionalized metal–organic framework as a luminescent probe for highly selective sensing of Fe3+ ions?
  Zhonghua Xiang,Chuanqi Fang,Sanhua Leng,Dapeng Cao J. Mater. Chem. A, 2014,2, 7662-7665
• 2. An asymmetric supercapacitor based on controllable WO3 nanorod bundle and alfalfa-derived porous carbon?
  Kanjun Sun,Fengting Hua,Shuzhen Cui,Yanrong Zhu,Hui Peng,Guofu Ma RSC Adv., 2021,11, 37631-37642
• 3. An air-stable organometallic polymer containing titanafluorene moieties obtained by the Sonogashira–Hagihara cross-coupling polycondensation?
  Alvin Tanudjaja,Shinsuke Inagi,Fusao Kitamura,Toshikazu Takata,Ikuyoshi Tomita Dalton Trans., 2021,50, 3037-3043
• 4. An atom efficient route to N-aryl and N-alkyl pyrrolines by transition metal catalysis?
  Supaporn Sawadjoon,Joseph S. M. Samec Org. Biomol. Chem., 2011,9, 2548-2554
• 5. An automatic determination of thoria in thoria-urania mixtures
  Analyst, 1966,91, 208-210

• Solvents and Organic Chemicals Organic Compounds Organoheterocyclic compounds Quinolines and derivatives Aminoquinolines and derivatives

6-Methoxyquinolin-8-amine (CAS No. 90-52-8): A Versatile Chemical Compound with Diverse Applications

6-Methoxyquinolin-8-amine (CAS No. 90-52-8) is a significant chemical compound that has garnered attention in various scientific and industrial fields. This compound, also known as 8-amino-6-methoxyquinoline, belongs to the quinoline family, which is renowned for its diverse biological and chemical properties. The unique structure of 6-methoxyquinolin-8-amine makes it a valuable intermediate in the synthesis of pharmaceuticals, agrochemicals, and specialty chemicals.

The molecular formula of 6-methoxyquinolin-8-amine is C₁₀H₁₀N₂O, and it features a methoxy group at the 6-position and an amino group at the 8-position of the quinoline ring. This structural arrangement contributes to its distinct chemical reactivity and solubility properties. Researchers and industry professionals often seek 6-methoxyquinolin-8-amine for its potential applications in drug discovery, material science, and catalysis.

One of the most prominent applications of 6-methoxyquinolin-8-amine is in the pharmaceutical industry. The quinoline scaffold is a common motif in many bioactive molecules, and modifications such as the introduction of a methoxy group can significantly alter the compound's pharmacological properties. Recent studies have explored the use of 6-methoxyquinolin-8-amine as a building block for antimalarial, anticancer, and antimicrobial agents. Its ability to interact with biological targets makes it a promising candidate for further drug development.

In addition to its pharmaceutical applications, 6-methoxyquinolin-8-amine is also utilized in the agrochemical sector. The compound's structural features enable it to act as a key intermediate in the synthesis of pesticides and herbicides. With the growing demand for sustainable agricultural practices, researchers are investigating the potential of 6-methoxyquinolin-8-amine-derived compounds to develop eco-friendly crop protection solutions.

The chemical industry also benefits from the versatility of 6-methoxyquinolin-8-amine. Its reactivity allows it to participate in various organic transformations, making it a valuable reagent in synthetic chemistry. For instance, it can be used in the preparation of dyes, pigments, and fluorescent markers. The compound's ability to form stable complexes with metals has also sparked interest in its use for catalytic applications and material science.

Recent advancements in synthetic methodologies have made 6-methoxyquinolin-8-amine more accessible to researchers and manufacturers. Innovations in green chemistry and continuous flow synthesis have improved the efficiency and sustainability of its production. These developments align with the global trend toward environmentally friendly chemical processes, making 6-methoxyquinolin-8-amine a compound of interest for sustainable industrial applications.

The market for 6-methoxyquinolin-8-amine is expected to grow in the coming years, driven by its expanding applications in pharmaceuticals, agrochemicals, and specialty chemicals. Industry reports highlight the increasing demand for quinoline derivatives, with 6-methoxyquinolin-8-amine being a key player in this market. Companies specializing in fine chemicals and custom synthesis are actively offering this compound to meet the needs of research institutions and industrial clients.

For researchers working with 6-methoxyquinolin-8-amine, it is essential to consider its physical and chemical properties. The compound typically appears as a light yellow to brown crystalline powder, with a melting point ranging between 120-125°C. It is soluble in organic solvents such as ethanol, methanol, and dimethyl sulfoxide (DMSO), but has limited solubility in water. Proper handling and storage conditions are recommended to maintain its stability and purity.

In conclusion, 6-methoxyquinolin-8-amine (CAS No. 90-52-8) is a multifaceted compound with significant potential across multiple industries. Its unique chemical structure and reactivity make it a valuable asset in drug discovery, agrochemical development, and material science. As research continues to uncover new applications for this compound, its importance in the chemical and pharmaceutical sectors is expected to rise. For those seeking a reliable and versatile chemical intermediate, 6-methoxyquinolin-8-amine is undoubtedly a compound worth considering.

• 67472-57-5(5-hydroxy-6-methoxy-8-aminoquinoline)
• 1216228-63-5(3-Amino-7-methoxyquinoline dihydrochloride)
• 61895-55-4(8-Quinolinamine, 6-methoxy-5-(4-methoxyphenoxy)-)
• 6938-02-9(5,6-Dimethoxy-8-quinolinamine)
• 29507-86-6(6-Methoxyquinolin-3-amine)
• 30465-68-0(5-methoxyquinolin-8-amine)
• 312693-53-1(8-Quinolinamine,6-methoxy-, hydrobromide (1:1))
• 13838-47-6(5-Methoxy-1H-indol-7-amine)
• 87199-83-5(7-Methoxyquinolin-3-amine)
• 881668-93-5(5-methoxyquinolin-3-amine)