51282-90-7

Usage

Uses

Used in Pharmaceutical Industry:
2-Hydroxy-5-methylbenzonitrile is used as an intermediate in the synthesis of various drugs, including hydroxychloroquine, which is utilized for treating malaria and autoimmune diseases.
Used in Agrochemical Industry:
2-hydroxy-5-methylbenzonitrile also serves as an intermediate in the production of pesticides, contributing to the development of agrochemicals that protect crops and enhance agricultural productivity.
Used for Antimicrobial Purposes:
2-Hydroxy-5-methylbenzonitrile is used as an antimicrobial agent due to its inherent antimicrobial properties, making it a potentially valuable compound for applications where microbial control is necessary.
Used for Antioxidant Applications:
The antioxidant properties of 2-hydroxy-5-methylbenzonitrile make it suitable for use in formulations that require protection against oxidative damage, which can be beneficial in various industrial and pharmaceutical settings.

Upstream product

• 53078-70-9 2-methoxy-5-methylbenzonitrile 
• 1269431-24-4 2-(methoxymethoxy)-5-methylbenzonitrile 
• 106-44-5 p-cresol 
• 556-64-9 methyl thiocyanate 
• 1116093-68-5 5-methyl-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzonitrile 
• 620-22-4 3-Methylbenzonitrile 
• 55305-43-6 N-cyano-N-phenyl-p-toluenesulfonamide 
• 613-84-3 2-hydroxy-5-methylbenzaldehyde 
• 22002-45-5 2-bromo-4-methylanisole 

Downstream Products

• 1268833-76-6 2-(5,6-dihydro-4H-1,3-oxazin-2-yl)-4-methylphenol 
• 73289-79-9 5-formyl-2-hydroxybenzonitrile 
• 1380495-84-0 C₁₀H₁₀N₂O₂ 
• 1293960-99-2 C₁₆H₁₂N₂O 
• 1293960-91-4 C₁₇H₁₅NO₃ 
• 51282-88-3 2-Cyan-4-methylphenoxyessigsaeure-aethylester 
• 1042334-14-4 (2-cyano-4-methylphenyl)trifluoromethanesulphonate 

Relevant academic research and scientific papers

Phosphination of Phenol Derivatives and Applications to Divergent Synthesis of Phosphine Ligands

We describe a general and efficient protocol for the synthesis of organophosphine compounds from phenols and phosphines (R2PH) via a metal-free C-O bond cleavage and C-P bond formation process. This approach exhibits broad substrate scope and excellent functional group tolerance. The synthetic utilities of this protocol were demonstrated by the synthesis of chiral ligands via the various transformations of cyano groups and their applications in asymmetric catalysis.

Sequential Ir/Cu-Mediated Method for the Meta-Selective C-H Radiofluorination of (Hetero)Arenes

This article describes a sequential Ir/Cu-mediated process for the meta-selective C-H radiofluorination of (hetero)arene substrates. In the first step, Ir-catalyzed C(sp2)-H borylation affords (hetero)aryl pinacolboronate (BPin) esters. The intermediate organoboronates are then directly subjected to copper-mediated radiofluorination with [18F]tetrabutylammonium fluoride to afford fluorine-18 labeled (hetero)arenes in high radiochemical yield and radiochemical purity. This entire process is performed on a benchtop without Schlenk or glovebox techniques and circumvents the need to isolate (hetero)aryl boronate esters. The reaction was automated on a TracerLab FXFN module with 1,3-dimethoxybenzene and a meta-tyrosine derivative. The products, [18F]1-fluoro-3,5-dimethoxybenzene and an 18F-labeled meta-tyrosine derivative, were obtained in 37 ± 5% isolated radiochemical yield and >99% radiochemical purity and 25% isolated radiochemical yield and 99% radiochemical purity, and 0.52 Ci/μmol (19.24 GBq/μmol) molar activity (Am), respectively.

Lewis Acid-Mediated Cyanation of Phenols Using N-Cyano-N-phenyl-p-toluenesulfonamide

Lewis acid-mediated cyanation of phenol derivatives with N-cyano-N-phenyl-p-toluenesulfonamide (NCTS) has been developed. The reaction proceeded efficiently with high regioselectivity to produce aromatic nitriles in moderate to excellent yields, which provides a direct and practical access to valuable products. (Figure presented.).

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

Facile one-pot transformation of phenols into o-cyanophenols

The treatment of phenols with paraformaldehyde in the presence of MgCl2 and Et3N in THF at 80 C, followed by reaction with molecular iodine and aq. ammonia at room temperature provided the corresponding o-cyanophenols in moderate to good yields. The present reaction is a one-pot transformation of phenols into o-cyanophenols using much less expensive reagents than are typically used; the reaction is free of both transition-metals and cyanide. The utility of this reaction was highlighted during our preparation of Febuxostat from p-bromophenol.

One-pot conversion of aromatic bromides and aromatics into aromatic nitriles via aryllithiums and their DMF adduct

Various aromatic bromides and iodides were smoothly converted into the corresponding aromatic nitriles in good to moderate yields by the treatment with n-butyllithium and subsequently DMF, followed by treatment with molecular iodine in aq NH3. The same treatment of typical aromatics and heteroaromatics with n-butyllithium and subsequently DMF, followed by treatment with molecular iodine in aq NH3 also provided the corresponding aromatic nitriles in good yields. Moreover, the same treatment of aromatic bromides and aromatics with half amount of DIH (1,3-diiodo-5,5- dimethylhydantoin) instead of molecular iodine worked effectively to give the corresponding aromatic nitriles, respectively, in good yields. These reactions are novel and environmentally benign one-pot methods for the preparation of aromatic nitriles from aromatic bromides and aromatics, respectively, through the formation of aryllithiums and their DMF adducts.

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.

BENZOFUROPYRIMIDINONES AS PROTEIN KINASE INHIBITORS

A compound according to formula I: or a pharmaceutically acceptable salt thereof; wherein R1, R2, R3a, R3b, R3c and R3d are as defined in the specification, pharmaceutical compositions thereof, and methods of use thereof.

MODULATORS OF THE METABOTROPIC GLUTAMATE RECEPTOR SUBTYPE 5 AND USES THEREOF

Disclosed are compounds and pharmaceutically acceptable salts, which are modulators of the metabotropic glutamate receptor 5, for use in treating drug abuse and other mental disorders, for example, a compound of Formula (I), wherein X, Y, and R1/sup

CARBAMOYL-TYPE BENZOFURAN DERIVATIVES

The present invention provides a carbamoyl-type benzofuran derivative of the formula [1]: wherein Ring Z is a group of the formula: etc.; A is a single bond, and the like; Y is a cycloalkanediyl group, etc.; R4 and R5 are the same or different and each is an optionally substituted lower alkyl group, etc.; R1 is a halogen atom, etc.; Ring B of the formula: is an optionally substituted benzene ring; and R3 is a hydrogen atom, etc., or a pharmaceutically acceptable salt thereof, which is useful as an FXa inhibitor.