51282-90-7

Basic information

• Product Name: 2-hydroxy-5-methylbenzonitrile
• Synonyms: 2-hydroxy-5-methylbenzonitrile;2-Cyano-4-methylphenol;2-Cyano-p-cresol;5-Methyl-2-hydroxybenzonitrile
• CAS NO: 51282-90-7
• Molecular Formula: C₈H₇NO
• Molecular Weight: 133.14728
• Mol File: 51282-90-7.mol
• Article Data: 14

Chemical Properties

• Melting Point: 100-102 °C
• Boiling Point: 277.4±28.0 °C(Predicted)
• Appearance: /
• Density: 1.17±0.1 g/cm3(Predicted)
• PKA: 7.47±0.18(Predicted)
• CAS DataBase Reference: 2-hydroxy-5-methylbenzonitrile(CAS DataBase Reference)
• NIST Chemistry Reference: 2-hydroxy-5-methylbenzonitrile(51282-90-7)
• EPA Substance Registry System: 2-hydroxy-5-methylbenzonitrile(51282-90-7)

Safety Data

• Hazardous Substances Data: 51282-90-7(Hazardous Substances Data)

Usage

Description

2-Hydroxy-5-methylbenzonitrile, also known as salicylmandelonitrile, is a chemical compound belonging to the class of benzonitriles. It features a hydroxyl group and a nitrile group attached to a benzene ring, which imparts it with unique chemical properties suitable for a variety of applications.

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

Downstream Products

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

Relevant articles and documents

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.

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.).

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.