Production Method 1

2238191-79-0

94444-96-9

Reaction Conditions

1.1 Reagents: Hantzsch ester Catalysts: Diisopropylethylamine ,  Copper(1+), [1,1′-[1,1′-binaphthalene]-2,2′-diylbis[1,1-diphenylphosphine-κP]](2… Solvents: Tetrahydrofuran ;  24 h

Reference

Visible-Light-Mediated N-Desulfonylation of N-Heterocycles Using a Heteroleptic Copper(I) Complex as a Photocatalyst

Hunter, Cameron J.; Boyd, Michael J. ; May, Gregory D.; Fimognari, Robert, Journal of Organic Chemistry, 2020, 85(13), 8732-8739

Production Method 2

249933-71-9

94444-96-9

Reaction Conditions

1.1 Reagents: Magnesium Solvents: Methanol ;  3 h, rt

Reference

Preparation of indazole and application of said indazole in synthesis of medicine

, China, , ,

Production Method 3

102-50-1

94444-96-9

Reaction Conditions

1.1 Reagents: Sodium nitrite Solvents: Acetic acid ,  Water
1.2 Reagents: Triethylamine

Reference

Aminopiperidine indazoles as orally efficacious melanin concentrating hormone receptor-1 antagonists

Vasudevan, Anil; Souers, Andrew J.; Freeman, Jennifer C.; Verzal, Mary K.; Gao, Ju; et al, Bioorganic & Medicinal Chemistry Letters, 2005, 15(23), 5293-5297

Production Method 4

102-50-1

94444-96-9

Reaction Conditions

1.1 Reagents: Acetic anhydride ,  Triethylamine Solvents: Dichloromethane ;  rt → 0 °C; 1 h, rt; rt → 0 °C
1.2 Reagents: Hydrochloric acid Solvents: Acetic acid ,  Water ;  rt → -5 °C
1.3 Reagents: Sodium nitrite Solvents: Water ;  1 h, -5 °C
1.4 Reagents: Water ;  10 min, 0 °C
1.5 Solvents: Toluene ;  1.5 h, rt → 80 °C

Reference

Preparation of benzimidazoles and analogs and their use as protein kinase inhibitors

, World Intellectual Property Organization, , ,

Production Method 5

94444-96-9

Reaction Conditions

Reference

New Practical Synthesis of Indazoles via Condensation of o-Fluorobenzaldehydes and Their O-Methyloximes with Hydrazine

Lukin, Kirill; Hsu, Margaret C.; Fernando, Dilinie; Leanna, M. Robert, Journal of Organic Chemistry, 2006, 71(21), 8166-8172

Production Method 6

249933-71-9

94444-96-9

Reaction Conditions

1.1 Reagents: Magnesium Solvents: Methanol ;  3 h, rt
1.2 Solvents: Water ;  rt

Reference

Copper(I) Oxide-Mediated Cyclization of o-Haloaryl N-Tosylhydrazones: Efficient Synthesis of Indazoles

Tang, Meng; Kong, Yuanfang; Chu, Bingjie; Feng, Dan, Advanced Synthesis & Catalysis, 2016, 358(6), 926-939

Production Method 7

14874-70-5

94444-96-9

Reaction Conditions

1.1 Reagents: Potassium acetate Catalysts: 18-Crown-6 Solvents: Chloroform ;  rt; 3 h, rt

Reference

Toward Biophysical Probes for the 5-HT3 Receptor: Structure-Activity Relationship Study of Granisetron Derivatives

Vernekar, Sanjeev Kumar V.; Hallaq, Hasan Y.; Clarkson, Guy; Thompson, Andrew J.; Silvestri, Linda; et al, Journal of Medicinal Chemistry, 2010, 53(5), 2324-2328

Production Method 8

14874-70-5

94444-96-9

Reaction Conditions

1.1 Reagents: Potassium acetate Catalysts: 18-Crown-6 Solvents: Chloroform ;  2 h, rt

Reference

Synthesis of new dehydro 2-azatryptophans and derivatives via Heck cross-coupling reactions of 3-iodoindazoles with methyl 2-(acetylamino)acrylate

Crestey, Francois; Collot, Valerie; Stiebing, Silvia; Rault, Sylvain, Synthesis, 2006, (20), 3506-3514

Production Method 9

7507-86-0

94444-96-9

Reaction Conditions

1.1 Reagents: Cesium carbonate Catalysts: Palladium diacetate ,  BINAP Solvents: Toluene ;  10 min, 80 °C
1.2 Reagents: Benzophenone hydrazone ;  16 h, 100 °C
1.3 Reagents: p-Toluenesulfonic acid Solvents: Tetrahydrofuran ,  Water ;  1 h, 100 °C

Reference

A general synthesis of diversely substituted indazoles and hetero-aromatic derivatives from o-halo-(het)arylaldehydes or -phenones

Dubost, Emmanuelle; Stiebing, Silvia; Ferrary, Thibault; Cailly, Thomas; Fabis, Frederic; et al, Tetrahedron, 2014, 70(44), 8413-8418

Production Method 10

94444-96-9

Reaction Conditions

Reference

Competitive pathways in the reaction between aromatic azosulfides and enolates in DMSO

Dell'erba, Carlo; Novi, Marino; Petrillo, Giovanni; Tavani, Cinzia, Phosphorus, 1993, 74(1-4), 409-10

Production Method 11

14874-70-5

94444-96-9

Reaction Conditions

1.1 Reagents: Potassium acetate ,  18-Crown-6 Solvents: Chloroform

Reference

Sonogashira cross-coupling reaction of 3-iodoindazoles with various terminal alkynes: a mild and flexible strategy to design 2-aza tryptamines

Arnautu, Anca; Collot, Valerie; Ros, Javier Calvo; Alayrac, Carole; Witulski, Bernhard; et al, Tetrahedron Letters, 2002, 43(15), 2695-2697

Production Method 12

94444-96-9

Reaction Conditions

1.1 Reagents: Cesium carbonate Catalysts: N,N′-Dimethylethylenediamine ,  Cuprous iodide Solvents: Dimethylformamide ;  5 h, 120 °C

Reference

A novel copper-catalyzed, hydrazine-free synthesis of N-1 unsubstituted 1H-indazoles using stable guanylhydrazone salts as substrates

Rekowski, Szymon P.; Kroener, Bettina K.; Kathuria, Deepika; Wani, Aabid A.; Chourasiya, Sumit S.; et al, Tetrahedron, 2021, 91,

Production Method 13

67567-42-4

94444-96-9

Reaction Conditions

1.1 Reagents: Sodium hydroxide Solvents: Methanol ;  overnight, 80 °C; 80 °C → rt
1.2 Reagents: Hydrochloric acid Solvents: Water ;  pH 1

Reference

Synthesis of 3-(2-Hydroxyaryl)indazole Derivatives through Radical O-Arylation and [3,3]-Rearrangement from N-Hydroxyindazoles and Diaryliodonium Salts

Nie, Shu-Min; Zhang, Xu; Wang, Zhi-Xin; Su, Gui-Fa ; Pan, Cheng-Xue; et al, Advanced Synthesis & Catalysis, 2022, 364(22), 3782-3788

Production Method 14

672-13-9

94444-96-9

Reaction Conditions

1.1 Reagents: Hydrazine hydrochloride (1:?) Solvents: Ethanol ;  3 h, reflux

Reference

Synthesis, antifungal activity and qsar of novel pyrazole amides as succinate dehydrogenase inhibitors

Du, Shijie; Li, Zhonghao; Tian, Zaimin; Xu, Lu, Heterocycles, 2018, 96(1), 74-85

Production Method 15

102-50-1

94444-96-9

Reaction Conditions

1.1 Reagents: Acetic acid ,  Sodium nitrite ,  Hydrochloric acid ,  Ammonium tetrafluoroborate Solvents: Water ;  0 °C → rt
1.2 Reagents: Potassium acetate Solvents: Ethyl acetate

Reference

Discovery and SAR of spirochromane Akt inhibitors

Kallan, Nicholas C.; Spencer, Keith L.; Blake, James F.; Xu, Rui; Heizer, Justin; et al, Bioorganic & Medicinal Chemistry Letters, 2011, 21(8), 2410-2414

Production Method 16

14874-70-5

94444-96-9

Reaction Conditions

1.1 Reagents: Potassium acetate Catalysts: 18-Crown-6 Solvents: Chloroform ;  2 h, rt

Reference

Preparation of quinolines, indazoles, and their analogs as thyroid receptor agonists

, World Intellectual Property Organization, , ,

Production Method 17

102-50-1

94444-96-9

Reaction Conditions

Reference

Product class 2: 1H- and 2H-indazoles

Stadlbauer, W., Science of Synthesis, 2002, 12, 227-324

5-Methoxy-1H-indazole Raw materials

• 2-Hydroxy-5-methoxybenzaldehyde
• 5-Methoxy-1-[(4-methylphenyl)sulfonyl]-1H-indazole
• Borate(1-),tetrafluoro-
• 4-Methoxy-2-methylaniline
• 2-Bromo-5-methoxybenzaldehyde
• (5-methoxy-2-nitrophenyl)methanamine
• 1H-Indazole, 5-methoxy-1-(phenylsulfonyl)-

5-Methoxy-1H-indazole Preparation Products

• 5-Methoxy-1H-indazole (94444-96-9)

• 1. Fe3O4 nanoclusters highly dispersed on a porous graphene support as an additive for improving the hydrogen storage properties of LiBH4?
  Guang Xu,Wei Zhang,Ying Zhang,Xiaoxia Zhao,Ping Wen,Di Ma RSC Adv., 2018,8, 19353-19361
• 2. Evidence of CO2 molecule acting as an electron acceptor on a nanoporous metal–organic-framework MIL-53 or Cr3+(OH)(O2C–C6H4–CO2)?
  Alexandre Vimont,Arnaud Travert,Philippe Bazin,Jean-Claude Lavalley,Marco Daturi,Christian Serre,Gérard Férey,Sandrine Bourrelly,Philip L. Llewellyn Chem. Commun., 2007, 3291-3293
• 3. Fate of single walled carbon nanotubes in wetland ecosystems?
  Joseph H. Bisesi,Tara Sabo-Attwood Environ. Sci.: Nano, 2014,1, 574-583
• 4. Emergence of microfluidic wearable technologies
  Joo Chuan Yeo,Kenry Lab Chip, 2016,16, 4082-4090
• 5. Establishment and implications of a characterization method for magnetic nanoparticle using cell tracking velocimetry and magnetic susceptibility modified solutions
  Huading Zhang,Lee R. Moore,Maciej Zborowski,P. Stephen Williams,Shlomo Margel,Jeffrey J. Chalmers Analyst, 2005,130, 514-527

Comprehensive Overview of 5-Methoxy-1H-indazole (CAS No. 94444-96-9): Properties, Applications, and Research Insights

5-Methoxy-1H-indazole (CAS No. 94444-96-9) is a heterocyclic organic compound belonging to the indazole family, characterized by a methoxy group at the 5-position of its aromatic ring. This structural feature enhances its reactivity and makes it a valuable intermediate in pharmaceutical and agrochemical research. The compound's molecular formula, C₈H₈N₂O, and its unique indazole core have attracted significant attention in medicinal chemistry due to its potential bioactivity.

Recent studies highlight the growing interest in 5-Methoxy-1H-indazole derivatives for their role in drug discovery, particularly in targeting kinase inhibitors and GPCR modulators. Researchers are exploring its applications in designing novel therapeutics for inflammation, oncology, and neurological disorders. The compound's methoxy substitution is pivotal for improving metabolic stability and binding affinity, addressing key challenges in modern drug development.

From an industrial perspective, CAS 94444-96-9 is synthesized via multi-step organic reactions, including palladium-catalyzed cross-coupling and cyclization techniques. Its purity (>98%) and scalability are critical for high-value applications. Analytical methods such as HPLC and NMR spectroscopy ensure quality control, meeting stringent regulatory standards for research use.

Environmental and safety assessments of 5-Methoxy-1H-indazole emphasize its low ecotoxicity, aligning with green chemistry principles. Its biodegradability and minimal hazardous byproducts make it a sustainable choice for industrial applications. This aligns with the increasing demand for eco-friendly synthetic intermediates in the chemical sector.

In the context of AI-driven drug discovery, computational models predict 5-Methoxy-1H-indazole's interactions with biological targets, accelerating lead optimization. Platforms like AlphaFold and molecular docking simulations leverage its structural data to identify potential therapeutic pathways. Such innovations address frequent user queries on "indazole-based drug design" and "CAS 94444-96-9 applications in precision medicine."

Market trends indicate rising demand for custom indazole synthesis, driven by pharmaceutical R&D investments. Suppliers of 94444-96-9 prioritize GMP compliance and batch-to-batch consistency to support global research initiatives. This responds to common searches like "reliable 5-Methoxy-1H-indazole suppliers" and "indazole derivatives for clinical trials."

Future research directions may explore 5-Methoxy-1H-indazole's role in photopharmacology, where light-activated compounds offer spatiotemporal control in therapy. Its modifiable scaffold also holds promise for covalent inhibitor development, a hotspot in oncology research. These advancements cater to trending topics like "next-generation indazole therapeutics" and "CAS 94444-96-9 in targeted drug delivery."

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