14143-26-1

Basic information

• Product Name: 4-hydroxy-2-Methylbenzonitrile
• Synonyms: 4-hydroxy-2-Methylbenzonitrile;4-Cyano-3-methylphenol;NSC 210797;3-Methyl-4-cyanophenol
• CAS NO: 14143-26-1
• Molecular Formula: C₈H₇NO
• Molecular Weight: 133.14728
• Mol File: 14143-26-1.mol
• Article Data: 20

Chemical Properties

• Boiling Point: 297.4 °C at 760mmHg
• Flash Point: 133.7 °C
• Appearance: /
• Density: 1.17 g/cm³
• Vapor Pressure: 0.000764mmHg at 25°C
• Refractive Index: 1.575
• Storage Temp.: Inert atmosphere,Room Temperature
• PKA: 7.95±0.18(Predicted)
• CAS DataBase Reference: 4-hydroxy-2-Methylbenzonitrile(CAS DataBase Reference)
• NIST Chemistry Reference: 4-hydroxy-2-Methylbenzonitrile(14143-26-1)
• EPA Substance Registry System: 4-hydroxy-2-Methylbenzonitrile(14143-26-1)

Safety Data

• Hazardous Substances Data: 14143-26-1(Hazardous Substances Data)

Usage

General Description

4-hydroxy-2-Methylbenzonitrile, also known as p-cresol or 4-methylphenol, is a chemical compound with the formula C7H8O. It is a colorless to white crystalline solid with a distinctive phenolic odor. This chemical is commonly used in the production of antioxidants, as a disinfectant, and as an intermediate in the production of pharmaceuticals. It is also found in coal tar and tobacco smoke, and exposure to p-cresol can cause irritation to the skin, eyes, and respiratory tract. Additionally, it is considered to be a potential carcinogen.

InChI:InChI=1/C8H7NO/c1-6-4-8(10)3-2-7(6)5-9/h2-4,10H,1H3

Upstream product

• 7677-24-9 trimethylsilyl cyanide 
• 553-97-9 2-Methyl-1,4-benzoquinone 
• 122-46-3 3-acetoxytoluene 
• 1147550-11-5 ammonium thiocyanate 
• 108-39-4 3-methyl-phenol 
• 333-20-0 potassium thioacyanate 
• 505-14-6 thiocyanogen 
• 578-39-2 4-hydroxy-2-methylbenzoic acid 
• 888019-41-8 4-hydroxy-2-methylbenzamide 
• 50712-68-0 4-chloro-2-methylbenzonitrile 
• 67832-11-5 4-bromo-2-methylbenzonitrile 
• 21883-13-6 4-methoxy-2-methylbenzonitrile 
• 155912-29-1 4-hydroxy-2-methyl-benzaldehyde-oxime 
• 41438-18-0 4-hydroxy-2-methyl-benzaldehyde 

Downstream Products

• 1369807-40-8 4-iso-propoxy-2-methylbenzonitrile 
• 628333-29-9 3-(4-hydroxy-2-methyl-phenyl)-propionic acid ethyl ester 
• 41438-18-0 4-hydroxy-2-methyl-benzaldehyde 
• 1579956-88-9 4-((tert-butyldimethylsilyl)oxy)-2-methylbenzonitrile 
• 1259517-48-0 2-methyl-4-[({[2-(trimethylsilyl)ethyl]oxy}methyl)oxy]benzonitrile 
• 1259517-55-9 2-methyl-4-{[2-(methyloxy)ethyl]oxy}benzonitrile 
• 64580-34-3 2-methyl-4-(1-methyl-5-nitro-1H-imidazol-2-ylmethoxy)-benzonitrile 
• 644985-31-9 [4-(4,4-dimethyl-5-oxo-4,5-dihydro-1H-pyrazol-3-yl)-3-methyl-phenyl]-carbamic acid benzyl ester 
• 914296-76-7 4-(benzyloxy)-2-methylbenzonitrile 
• 57556-31-7 4-hydroxy-2-methylbenzoic acid methyl ester 
• 129249-09-8 4-(5-Hexyl-pyrimidin-2-yl)-benzoic acid 4-cyano-3-methyl-phenyl ester 

Relevant articles and documents

Discovery and characterization of a novel perylenephotoreductant for the activation of aryl halides

To develop a photocatalyst with catalytical activity for substrates with low reactivities is always highly desired. Herein, based on the principle of structure–property relationships, we rationally designed the natural product cercosporin, the naturally occurring perylenequinonoid pigment, to develop a novel organic perylenephotoreductant, hexacetyl reduced cercosporin (HARCP), through structural manipulation. Compared with cercosporin, HARCP shows prominent electrochemical and photophysical characteristics with greatly improved photoreductive activity, fluorescence lifetime and fluorescence quantum yield. These properties allowed HARCP as a powerful photoreductant to efficiently realize a series of benchmark reactions, including photoreduction, alkoxylation and hydroxylation to construct C–H and C–O bonds using aryl halides as substrates under mild conditions, all of which have never been achieved by the same photocatalyst. Thus, this study well supports the notion that the principle between structural manipulation and photocatalytic activity is of great significance to design customized photocatalysts for photoredox chemistry.

Photoinduced Hydroxylation of Organic Halides under Mild Conditions

Presented in this paper is photoinduced hydroxylation of organic halides, providing a mild access to a range of functionalized phenols and aliphatic alcohols. These reactions generally proceed under mild reaction conditions with no need for a photocatalyst or a strong base and show a wide substrate scope as well as excellent functional group tolerance. This work highlights the unique role of NaI that allows a challenging transformation to proceed under mild reaction conditions.

Synthesis of Phenols: Organophotoredox/Nickel Dual Catalytic Hydroxylation of Aryl Halides with Water

A highly effective hydroxylation reaction of aryl halides with water under synergistic organophotoredox and nickel catalysis is reported. The OH group of the resulting phenols originates from water, following deprotonation facilitated by an intramolecular base group on the ligand. Significantly, aryl bromides as well as less reactive aryl chlorides served as effective substrates to afford phenols with a wide range of functional groups. Without the need for a strong inorganic base or an expensive noble-metal catalyst, this process can be applied to the efficient preparation of diverse phenols and enables the hydroxylation of multifunctional pharmaceutically relevant aryl halides.