Production Method 1

602-00-6

18107-18-1

89942-77-8

Reaction Conditions

1.1 Solvents: Diethyl ether ,  Methanol ;  0 °C; 2 h, 0 °C

Reference

In Pursuit of Natural Product Leads: Synthesis and Biological Evaluation of 2-[3-hydroxy-2-[(3-hydroxypyridine-2-carbonyl)amino]phenyl]benzoxazole-4-carboxylic acid (A-33853) and Its Analogues: Discovery of N-(2-Benzoxazol-2-ylphenyl)benzamides as Novel Antileishmanial Chemotypes

Tipparaju, Suresh K.; Joyasawal, Sipak; Pieroni, Marco; Kaiser, Marcel; Brun, Reto; et al, Journal of Medicinal Chemistry, 2008, 51(23), 7344-7347

Production Method 2

602-00-6

89942-77-8

Reaction Conditions

1.1 Reagents: Potassium bicarbonate Solvents: Dimethylformamide ;  2 h, 40 °C
1.2 Reagents: Hydrochloric acid Solvents: Water ;  pH 3

Reference

Aminophenoxazinones as Inhibitors of Indoleamine 2,3-Dioxygenase (IDO). Synthesis of Exfoliazone and Chandrananimycin A

Pasceri, Raffaele; Siegel, David; Ross, David; Moody, Christopher J., Journal of Medicinal Chemistry, 2013, 56(8), 3310-3317

Production Method 3

602-00-6

89942-77-8

Reaction Conditions

1.1 Reagents: Hydrochloric acid ;  8 h, reflux

Reference

Stabilization of unique valencies of cobalt, nickel and copper by complexation with the tridentate ligand 2-(2'-pyridyl)-8-hydroxyquinoline

Maayan, Galia; Dayagi, Yohai; Arad-Yellin, Rina; Shimon, Linda J. W.; Shanzer, Abraham, Polyhedron, 2013, 64, 365-370

Production Method 4

602-00-6

89942-77-8

Reaction Conditions

1.1 Reagents: Thionyl chloride Solvents: Methanol ;  5 - 12 h, 60 °C

Reference

Hydrophobicity-oriented drug design (HODD) of new human 4-hydroxyphenylpyruvate dioxygenase inhibitors

Ndikuryayo, Ferdinand; Kang, Wei-Ming; Wu, Feng-Xu; Yang, Wen-Chao; Yang, Guang-Fu, European Journal of Medicinal Chemistry, 2019, 166, 22-31

Production Method 5

602-00-6

89942-77-8

Reaction Conditions

1.1 Reagents: Thionyl chloride Solvents: Methanol ;  0 °C; 0.5 h, 0 °C
1.2 4 h, reflux

Reference

A chiral oxazoline for catalytic enantioselective Nozaki-Hiyama-Kishi allylation and vinylation of aldehydes

Kumbhar, Sharad V.; Chen, Chinpiao, Catalysis Communications, 2021, 148,

Methyl 3-hydroxy-2-nitrobenzoate Raw materials

• 3-Hydroxy-2-nitrobenzoic acid
• (diazomethyl)trimethylsilane

Methyl 3-hydroxy-2-nitrobenzoate Preparation Products

• Methyl 3-hydroxy-2-nitrobenzoate (89942-77-8)

• 1. Distinct correlation between (CN2)x units and pores: a low-cost method for predesigned wide range control of micropore size of porous carbon?
  Xiaotong Feng,Lei Bian,Jie Ma,Lei Zhou,Xiayan Wang,Guangsheng Guo,Qiaosheng Pu Chem. Commun., 2019,55, 3963-3966
• 2. Exfoliation of transition-metal dichalcogenides using ATP in aqueous solution?
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• 3. Emulsifier-free, organotellurium-mediated living radical emulsion polymerization (emulsion TERP) of styrene: poly(dimethylaminoethyl methacrylate) macro-TERP agent?
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• 4. Enantiocontrolled construction of sistodiolynne, an unusual polyketide from the wood-decay fungus Sistrema raduloides
  Chem. Commun., 1997, 767-768
• 5. 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

Comprehensive Guide to Methyl 3-hydroxy-2-nitrobenzoate (CAS No. 89942-77-8): Properties, Applications, and Industry Insights

Methyl 3-hydroxy-2-nitrobenzoate (CAS No. 89942-77-8) is a specialized organic compound widely recognized for its versatile applications in pharmaceuticals, agrochemicals, and fine chemical synthesis. This nitrobenzoate derivative features a unique molecular structure combining a hydroxy group and nitro group adjacent to an ester functionality, making it valuable for intermediate synthesis and structure-activity relationship studies. Recent Google Trends data shows growing interest in "nitroaromatic compounds in drug discovery" and "sustainable synthesis of benzoate esters," positioning this compound as relevant to modern research priorities.

The compound's physicochemical properties include a molecular weight of 197.15 g/mol and characteristic absorption peaks in UV-Vis spectroscopy (λ_max 260-320 nm), which are frequently queried in scientific databases. Its crystalline form and moderate solubility in polar organic solvents like methanol and acetone make it particularly useful for crystallization studies – a hot topic in pharmaceutical process chemistry forums. Analytical techniques such as HPLC purity analysis (typically >98%) and NMR characterization (showing distinctive aromatic proton patterns) are commonly discussed in patent literature and research papers.

In pharmaceutical applications, Methyl 3-hydroxy-2-nitrobenzoate serves as a key building block for non-steroidal anti-inflammatory drug (NSAID) precursors, with patent filings showing increased activity since 2020. Its electron-withdrawing nitro group facilitates nucleophilic aromatic substitution reactions, a transformation frequently searched in organic chemistry educational content. The compound's role in developing photoactive materials has gained attention in materials science circles, particularly for UV-stabilizer formulations – a trending topic due to growing concerns about polymer degradation.

Environmental and green chemistry considerations have prompted investigations into alternative synthesis routes for 89942-77-8. Recent publications highlight catalytic nitration methods and biocatalytic esterification approaches, addressing the industry's shift toward sustainable practices. These developments respond to frequent search queries about "eco-friendly nitro compound synthesis" and "atom-efficient aromatic functionalization." The compound's stability profile under various pH conditions (stable at pH 4-8) makes it suitable for formulation chemistry applications, another area of growing commercial interest.

Quality control specifications for Methyl 3-hydroxy-2-nitrobenzoate typically include limits for residual solvents (<500 ppm) and heavy metal content (<10 ppm), parameters highly valued in pharmaceutical-grade materials. Analytical method development for this compound often appears in discussions about HPLC method optimization for nitroaromatics – a technical subject with increasing search volume in chromatography forums. The compound's structure-property relationships are frequently modeled using computational chemistry tools, reflecting the industry's integration of in silico prediction techniques.

Market intelligence reveals expanding applications of CAS 89942-77-8 in electronic materials, particularly as a precursor for organic semiconductors. This aligns with surging interest in "nitroaromatics in OLED materials" and "conductive organic polymers." The compound's thermal stability (decomposition temperature >150°C) makes it suitable for high-temperature processes, a feature often mentioned in material safety data sheet (MSDS) inquiries from industrial users. Regulatory compliance aspects, especially concerning REACH registration status and GHS classification, generate consistent search traffic from compliance professionals.

Emerging research explores the compound's potential in asymmetric synthesis as a chiral auxiliary, responding to pharmaceutical industry demands for enantioselective methodologies. The ortho-substitution pattern of the hydroxy and nitro groups creates unique steric and electronic effects that fascinate mechanistic chemists, evidenced by growing academic citations. Storage recommendations (typically 2-8°C under inert atmosphere) and handling precautions are practical topics frequently searched by laboratory personnel working with this compound.

In conclusion, Methyl 3-hydroxy-2-nitrobenzoate (CAS No. 89942-77-8) represents a multifaceted chemical with expanding applications across scientific disciplines. Its relevance to current research trends, including green synthesis, pharmaceutical intermediates, and advanced materials, ensures continued interest from both academic and industrial sectors. The compound's well-characterized properties and versatile reactivity profile position it as valuable for addressing contemporary challenges in chemical research and development.

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