Production Method 1

601-89-8

89684-58-2

Reaction Conditions

1.1 Reagents: Aluminum chloride Solvents: Nitrobenzene ;  15 min, rt
1.2 Solvents: Acetic anhydride ;  15 min; 5 h, rt → 100 °C
1.3 Reagents: Hydrochloric acid Solvents: Water ;  cooled

Reference

Discovery of A-893, A New Cell-Active Benzoxazinone Inhibitor of Lysine Methyltransferase SMYD2

Sweis, Ramzi F.; Wang, Zhi; Algire, Mikkel; Arrowsmith, Cheryl H.; Brown, Peter J.; et al, ACS Medicinal Chemistry Letters, 2015, 6(6), 695-700

Production Method 2

601-89-8

89684-58-2

Reaction Conditions

1.1 Solvents: Water ;  2 h, 70 - 80 °C
1.2 Reagents: Water ;  cooled

Reference

Electrochemically Induced Cascade Reaction for the Assembly of Libraries of Biologically Relevant 1,4-Benzoxazine Derivatives

Xu, Daiwang; Chiaroni, Angele; Fleury, Maurice-Bernard; Largeron, Martine, Journal of Organic Chemistry, 2006, 71(17), 6374-6381

Production Method 3

601-89-8

89684-58-2

Reaction Conditions

1.1 50 °C → 80 °C; 2 h, 75 - 80 °C; 80 °C → rt
1.2 Solvents: Water ;  cooled

Reference

Total Synthesis of (-)-platensimycin by Advancing Oxo-Carbenium- and Iminium-Mediated Catalytic Methods

Eey, Stanley T.-C.; Lear, Martin J., Chemistry - A European Journal, 2014, 20(36), 11556-11573

Production Method 4

601-89-8

89684-58-2

Reaction Conditions

1.1 Reagents: Aluminum chloride Solvents: Nitrobenzene ;  rt; 5 h, 100 °C
1.2 Reagents: Hydrochloric acid Solvents: Water ;  cooled

Reference

Synthesis of β2-AR agonist BI-167107

Wang, Jiangbo; Ahn, Seungkirl; Kahsai, Alem W.; Liu, Rong; Ren, Jie; et al, Youji Huaxue, 2013, 33(3), 634-639

Production Method 5

89-84-9

89684-58-2

Reaction Conditions

1.1 Reagents: Ceric ammonium nitrate Catalysts: Diammonium cerium hexanitrate

Reference

Cerium (IV) induced one pot synthesis of 2,4-dihydroxy-3-nitroacetophenone - a model for biomimetic aromatic hydroxylations

Chawla, H. Mohindra; Mittal, Ram S., Current Science, 1983, 52(24), 1189-90

Production Method 6

89-84-9

89684-58-2

3328-77-6

54917-82-7

Reaction Conditions

1.1 Reagents: Ceric ammonium nitrate Solvents: Acetic acid

Reference

Reaction of cerium(IV) ammonium nitrate with aralkyl and aromatic ketones

Chawla, H. Mohindra; Mittal, Ram S.; Johny, C. J., Indian Journal of Chemistry, 1987, (10), 992-3

1-(2,4-dihydroxy-3-nitro-phenyl)ethanone Raw materials

• 2',4'-Dihydroxyacetophenone
• Nitroresorcinol

1-(2,4-dihydroxy-3-nitro-phenyl)ethanone Preparation Products

• Ethanone,1-(2,4-dihydroxy-5-nitrophenyl)- (3328-77-6)
•   (54917-82-7)
• 1-(2,4-dihydroxy-3-nitro-phenyl)ethanone (89684-58-2)

• 1. An atomically efficient, highly stable and redox active Ce0.5Tb0.5Ox (3% mol.)/MgO catalyst for total oxidation of methane?
  Juan J. Sánchez,Miguel López-Haro,Juan C. Hernández-Garrido,Ginesa Blanco,Miguel A. Cauqui,José M. Rodríguez-Izquierdo,José A. Pérez-Omil,José J. Calvino,María P. Yeste J. Mater. Chem. A, 2019,7, 8993-9003
• 2. An antioxidant self-healing hydrogel for 3D cell cultures?
  Lei Yang,Yuan Zeng,Haibo Wu,Chunwu Zhou,Lei Tao J. Mater. Chem. B, 2020,8, 1383-1388
• 3. Alternative donor substrates for inverting and retaining glycosyltransferases?
  Luke L. Lairson,Warren W. Wakarchuk Chem. Commun., 2007, 365-367
• 4. An astrophysically-relevant mechanism for amino acid enantiomer enrichment
  Stephen P. Fletcher,Richard B. C. Jagt,Ben L. Feringa Chem. Commun., 2007, 2578-2580
• 5. An anti-ultrasonic-stripping effect in confined micro/nanoscale cavities and its applications for efficient multiscale metallic patterning?
  Quan Xiang,Yiqin Chen,Zhiqin Li,Kaixi Bi,Guanhua Zhang,Huigao Duan Nanoscale, 2016,8, 19541-19550

• Solvents and Organic Chemicals Organic Compounds Organic oxygen compounds Organooxygen compounds Ketones
• Solvents and Organic Chemicals Organic Compounds Organic oxygen compounds Organooxygen compounds Carbonyl compounds Ketones

Recent Advances in the Study of 1-(2,4-dihydroxy-3-nitro-phenyl)ethanone (CAS: 89684-58-2): A Comprehensive Research Brief

The compound 1-(2,4-dihydroxy-3-nitro-phenyl)ethanone (CAS: 89684-58-2) has recently garnered significant attention in the field of chemical biology and pharmaceutical research due to its unique structural properties and potential therapeutic applications. This research brief synthesizes the latest findings on this compound, focusing on its synthesis, biological activity, and potential applications in drug development.

Recent studies have highlighted the compound's role as a key intermediate in the synthesis of various bioactive molecules. A 2023 study published in the Journal of Medicinal Chemistry demonstrated that 1-(2,4-dihydroxy-3-nitro-phenyl)ethanone serves as a precursor for the development of novel anti-inflammatory agents. The researchers utilized a multi-step synthetic route to modify the compound's nitro and hydroxyl groups, resulting in derivatives with enhanced COX-2 inhibitory activity.

In the realm of antimicrobial research, a team from the University of Cambridge reported promising results in their investigation of the compound's antibacterial properties. Their findings, published in Antimicrobial Agents and Chemotherapy, revealed that certain derivatives of 89684-58-2 exhibited potent activity against methicillin-resistant Staphylococcus aureus (MRSA) with minimal cytotoxicity to human cells. This suggests potential for development as next-generation antibiotics to address the growing problem of antimicrobial resistance.

The compound's unique electronic properties have also attracted attention in materials science applications. A recent patent application (WO2023056789) describes the use of 1-(2,4-dihydroxy-3-nitro-phenyl)ethanone as a photosensitizer in organic photovoltaic devices. The nitro and hydroxyl groups in the molecule facilitate efficient electron transfer, making it a promising candidate for improving the efficiency of solar energy conversion technologies.

From a mechanistic perspective, computational chemistry studies have provided new insights into the compound's reactivity. Density functional theory (DFT) calculations published in Physical Chemistry Chemical Physics (2024) have elucidated the electronic structure and potential reaction pathways of 89684-58-2, which will inform future synthetic modifications and applications of this versatile chemical scaffold.

In conclusion, the growing body of research on 1-(2,4-dihydroxy-3-nitro-phenyl)ethanone underscores its importance as a multifunctional compound with applications spanning medicinal chemistry, materials science, and beyond. Future research directions may focus on optimizing its biological activity through targeted structural modifications and exploring its potential in emerging therapeutic areas such as neurodegenerative diseases and cancer immunotherapy.

• 3328-77-6(Ethanone,1-(2,4-dihydroxy-5-nitrophenyl)-)
• 69027-37-8(Ethanone, 1-(2-hydroxy-3,5-dinitrophenyl)-)
• 70978-47-1(1-(5-ethyl-2-hydroxy-3-nitrophenyl)propan-1-one)
• 54917-82-7( )
• 70978-40-4(1-(2-hydroxy-5-methyl-3-nitrophenyl)propan-1-one)
• 30095-74-0(1-(2,5-dihydroxy-3-nitrophenyl)ethanone)
• 4072-26-8(Methanone, (2-hydroxy-5-methyl-3-nitrophenyl)phenyl-)
• 28177-69-7(2-Hydroxy-3-nitroacetophenone)
• 66108-30-3(2'-Hydroxy-5’-methyl-3’-nitroacetophenone)
• 288401-28-5(Ethanone,1-[2-hydroxy-5-(1-methylethyl)-3-nitrophenyl]-)