39835-11-5

Usage

Uses

Used in Organic Synthesis:
2-Hydroxy-5-methoxybenzonitrile is used as a chemical intermediate for the synthesis of various organic compounds. Its unique structure, which includes a methoxy and hydroxy group on the benzene ring, allows it to participate in a range of chemical reactions, making it a valuable building block in the creation of more complex molecules.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 2-Hydroxy-5-methoxybenzonitrile is used as a precursor in the development of new drugs. Its reactivity and functional groups enable it to be incorporated into the molecular structures of potential therapeutic agents, contributing to the discovery of novel medications.
Used in Chemical Research:
2-Hydroxy-5-methoxybenzonitrile is also utilized in academic and industrial research settings as a model compound for studying the properties and reactions of benzonitriles. Its behavior under different conditions can provide insights into the broader class of nitrile compounds and their potential applications in various fields.

InChI:InChI=1/C8H7NO2/c1-11-7-3-2-6(5-9)8(10)4-7/h2-4,10H,1H3

Upstream product

• 17861-16-4 2-hydroxy-4-methoxybenzaldehyde oxime 
• 108-24-7 acetic anhydride 
• 556-64-9 methyl thiocyanate 
• 150-19-6 O-methylresorcine 
• 5446-02-6 4-methoxymethylsalicylate 
• 39835-05-7 6-methoxybenzo[d]isoxazole 
• 673-22-3 2-Hydroxy-4-methoxybenzaldehyde 
• 4107-65-7 2,4-dimethoxybenzonitrile 
• 94610-82-9 2-fluoro-4-methoxyphenyl nitrile 
• 79-24-3 Nitroethane 
• 6745-77-3 2-hydroxy-4-methoxy-benzamide 
• 82380-18-5 2-fluoro-4-hydroxybenzonitrile 
• 155912-26-8 1-[4-((E)-4-methoxyl-2-hydroxybenzylidene)]oxime 

Downstream Products

• 860594-96-3 2-(2,5-dimethoxy-3-methyl-phenoxy)-4-methoxy-benzonitrile 
• 4107-65-7 2,4-dimethoxybenzonitrile 
• 24599-58-4 2,5-dimethoxy toluene 
• 860562-27-2 2-(2,5-dimethoxy-3-methyl-phenoxy)-4-methoxy-benzoic acid 
• 224789-17-7 2-ethoxy-4-methoxybenzonitrile 
• 869789-23-1 C₁₁H₁₁NO₃ 
• 548472-47-5 2-isopropoxy-4-methoxy-benzonitrile 
• 548473-68-3 2-cyclopentyloxy-4-methoxy-benzonitrile 
• 398136-85-1 3-amino-N-(2,4-dichlorophenyl)-6-methoxybenzofuran-2-carboxamide 
• 182123-86-0 (3-Amino-6-methoxy-benzofuran-2-yl)-(3-nitro-phenyl)-methanone 
• 138642-60-1 (2-cyano-5-methoxyphenyl)trifluoromethanesulphonate 
• 1072878-89-7 (3-amino-6-methoxybenzofuran-2-yl)(3,4,5-trimethoxyphenyl)-methanone 
• 1422548-62-6 C₁₉H₁₈N₄O₂ 
• 1422548-37-5 C₁₇H₁₃N₃O₂ 

Relevant academic research and scientific papers

para-Selective Arylation of Arenes: A Direct Route to Biaryls by Norbornene Relay Palladation

Biaryl compounds are extremely important structural motifs in natural products, biologically active components and pharmaceuticals. Selective synthesis of biaryls by distinguishing the subtle reactivity difference of distal arene C?H bonds are significantly challenging. Herein, we describe para-selective C?H arylation, which is acheived by a unique combination of a meta-directing group and norbornene as a transient mediator. Upon direct meta-C?H palladation, one-bond relay palladation occurs in presence of norbornene and subsequently para-C?H arylation is achieved for sulfonates, phosphonates and phenols bearing 2,6-disubstitution patterns. The protocol is amenable to electron-deficient aryl iodides. Multisubstituted arenes and phenols are obtained by postsynthetic modification of the products. The protocol allows the synthesis of hexa-substituted benzene by sequential selective distal C?H functionalization.

Lewis acid-promoted site-selective cyanation of phenols

An efficient Lewis acid-promoted site-selective electrophilic cyanation of 3-substituted and 3,4-disubstituted phenols has been developed. The cyanation reactions using MeSCN as the cyanating reagent proceeded efficiently to afford a wide range of 2-hydroxybenzonitriles with high efficiency and excellent regioselectivity. This protocol could provide a practical method for the synthesis and modification of biologically active molecules.

Palladium-Catalyzed Remote meta-Selective C-H Bond Silylation and Germanylation

Selective meta-C-H activation of arenes to date has met with a limited number of functionalizations. Expanding the horizon of meta-C-H functionalization, herein we disclose an unprecedented meta-silylation and -germanylation protocol by employing a simple nitrile-based directing template. Longer linkers between the target site and the directing template were successfully explored for meta-silylation (sp2-? and sp2-ζ). Additionally, synthetic utility was demonstrated with several postsynthetic elaborations and with a formal synthesis of TAC101, a promising drug for the treatment of lung cancer.

Rhodium-Catalyzed meta-C?H Functionalization of Arenes

Rhodium-catalyzed ortho-C?H functionalization is well known in the literature. Described herein is the Xphos-supported rhodium catalysis of meta-C?H olefination of benzylsulfonic acid and phenyl acetic acid frameworks with the assistance of a para-methoxy-substituted cyano phenol as the directing group. Complete mono-selectivity is observed for both scaffolds. A wide range of olefins and functional groups attached to arene are tolerated in this protocol.

Perfluoroalkanosulfonyl fluoride: A useful reagent for dehydration of aldoximes to nitriles

The reaction of a variety of aldoximes with perfluoroalkanosulfonyl fluoride in the presence of 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) in dichloromethane smoothly generated the corresponding nitriles in 70%-95% yields.

Chromatography-free entry to substituted salicylonitriles: Mitsunobu-triggered domino reactions of salicylaldoximes

A mild and efficient one-pot procedure is described to transform salicylaldoximes into salicylonitriles using Mitsunobu chemistry. The reactions proceed through the corresponding 1,2-benzisoxazoles that undergo the Kemp elimination in situ to generate the

Utility of Nitrogen Extrusion of Azido Complexes for the Synthesis of Nitriles, Benzoxazoles, and Benzisoxazoles

The utility of the nitrogen extrusion reaction of azido complexes, generated in situ from the corresponding aldehydes or ketones with TMSN3 in the presence of ZrCl4 or TfOH, has been described. These azido complexes could undergo three different pathways, depending on the substrates. First, azido methanolate complexes or imine diazonium ions could lead to benzisoxazole products via an intramolecular nucleophilic substitution. Second, imine diazonium ions could also undergo either the elimination of proton to provide nitrile products in good to excellent yields or an aryl migration, followed by an intramolecular nucleophilic addition, to give benzoxazole products in good yields.

Synthesis and biological evaluation of N-aryl-7-methoxybenzo[b]furo[3,2-d] pyrimidin-4-amines and their N-arylbenzo[b]thieno[3,2-d]pyrimidin-4-amine analogues as dual inhibitors of CLK1 and DYRK1A kinases

Novel N-aryl-7-methoxybenzo[b]furo[3,2-d]pyrimidin-4-amines (1) and their N-arylbenzo[b]thieno[3,2-d]pyrimidin-4-amine analogues (2) were designed and prepared for the first time via microwave-accelerated multi-step synthesis. Various anilines were conden

Heterogeneous catalytic method for the conversion of aldoximes into nitriles using molecular sieve modified with Copper(II)

A simple heterogeneous metal-catalyzed method was developed for the transformation of aldoximes into nitriles. Molecular sieve (4 A) modified with copper(II) proved to be an efficient catalyst for the conversion. Supplemental materials are available for this article. Go to the publisher's online edition of Synthetic Communications to view the free supplemental file.

A catalytic route to ampakines and their derivatives

A catalytic domino reaction that efficiently provides access to an important class of heterocycles, the ampakines, is reported. Our approach is based on the cobalt-catalyzed hydroformylation of dihydrooxazines and allows for the facile synthesis of the pharmaceutically interesting compound CX-614 and related substances.