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

General Description

2-hydroxy-5-methylbenzonitrile, also known as salicylmandelonitrile, is a chemical compound that belongs to the class of benzonitriles. It is commonly used in the pharmaceutical and agrochemical industries as an intermediate in the synthesis of various drugs and pesticides. 2-hydroxy-5-methylbenzonitrile has a hydroxyl group and a nitrile group attached to a benzene ring, giving it unique chemical properties that make it suitable for a wide range of applications. 2-hydroxy-5-methylbenzonitrile is known for its involvement in the synthesis of salicylaldehyde, which is a key part of the synthesis of the drug hydroxychloroquine, used to treat malaria and autoimmune diseases. Additionally, it is known to possess antimicrobial and antioxidant properties, making it a potentially valuable compound for various industrial and pharmaceutical purposes.

Upstream product

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

Downstream Products

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

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.