58537-99-8

Basic information

• Product Name: 4-HYDROXY-2,6-DIMETHYLBENZONITRILE
• Synonyms: 2,6-DIMETHYL-4-HYDROXYBENZONITRILE;4-HYDROXY-2,6-DIMETHYLBENZONITRILE;4-HYDROXY-2,6-DIMETHYLBENZONITRILE ---POWDER, 98%---;4-Cyano-3,5-dimethylphenol, 2-Cyano-5-hydroxy-m-xylene;Benzonitrile, 4-hydroxy-2,6-dimethyl-
• CAS NO: 58537-99-8
• Molecular Formula: C₉H₉NO
• Molecular Weight: 147.17
• Product Categories: Aromatic Nitriles;Phenyls & Phenyl-Het;Phenyls & Phenyl-Het
• Mol File: 58537-99-8.mol
• Article Data: 6

Chemical Properties

• Melting Point: 176 °C
• Boiling Point: 313.7°Cat760mmHg
• Flash Point: 143.5°C
• Appearance: off-white Solid Not available
• Density: 1.13g/cm³
• Vapor Pressure: 0.000265mmHg at 25°C
• Refractive Index: 1.563
• Storage Temp.: Sealed in dry,Room Temperature
• PKA: 8.08±0.23(Predicted)
• CAS DataBase Reference: 4-HYDROXY-2,6-DIMETHYLBENZONITRILE(CAS DataBase Reference)
• NIST Chemistry Reference: 4-HYDROXY-2,6-DIMETHYLBENZONITRILE(58537-99-8)
• EPA Substance Registry System: 4-HYDROXY-2,6-DIMETHYLBENZONITRILE(58537-99-8)

Safety Data

• Hazard Codes: Xn,Xi
• Statements: 20/21/22-36/37/38-36
• Safety Statements: 26-36/37/39-36/37-22
• RIDADR: 3276
• Hazardous Substances Data: 58537-99-8(Hazardous Substances Data)

Usage

Chemical Properties

White crystal

InChI:InChI=1/C9H9NO/c1-6-3-8(11)4-7(2)9(6)5-10/h3-4,11H,1-2H3

Upstream product

• 7463-51-6 4-bromo-3,5-dimethylphenol 
• 557-21-1 dicyanozinc 
• 333-20-0 potassium thioacyanate 
• 108-68-9 3,5-Dimethylphenol 
• 378185-88-7 tert-butyl(4-iodo-3,5-dimethylphenoxy)dimethylsilane 
• 80826-86-4 4-iodo-3,5-dimethylphenol 
• 1004-36-0 2,6-dimethylpyrone 
• 105-56-6 ethyl 2-cyanoacetate 
• 7677-24-9 trimethylsilyl cyanide 
• 527-61-7 2,6-dimethyl-1,4-benzoquinone 
• 854854-57-2 4-acetoxy-2,6-dimethyl-benzonitrile 

Downstream Products

• 415913-74-5 4-hydroxy-2,6-dimethyl-3-nitro-benzonitrile 
• 913346-13-1 4-(1-Cyclopropanecarbonyl-2-cyclopropyl-2-oxo-ethoxy)-2,6-dimethyl-benzonitrile 
• 913346-19-7 4-(2-cyclopropyl-2-oxoethoxy)-2,6-dimethylbenzonitrile 
• 913346-12-0 4-[1-(cyclopropylcarbonyl)-2-oxopropoxy]-2,6-dimethylbenzonitrile 
• 1174495-39-6 C₂₅H₂₄N₂O₄ 
• 1174495-31-8 4-({3-cyclopropyl-5-methyl-1-[(methylsulfanyl)methyl]-1H-pyrazol-4-yl}oxy)-2,6-dimethylbenzonitrile 
• 1174495-34-1 C₁₈H₂₁N₃OS 
• 807628-83-7 3-bromo-4-methoxy-2,6-dimethylbenzonitrile 
• 1207102-01-9 C₉H⁽²⁾H₈NO 
• 114820-17-6 4-methoxy-2,6-dimethyl-benzoic acid amide 

Relevant articles and documents

Metal-Free Regioselective Monocyanation of Hydroxy-, Alkoxy-, and Benzyloxyarenes by Potassium Thiocyanate and Silica Sulfuric Acid as a Cyanating Agent

A novel and efficient metal- and solvent-free regioselective para-C-H cyanation of hydroxy-, alkoxy-, and benzyloxyarene derivatives has been introduced, using nontoxic potassium thiocyanate as a cyanating reagent in the presence of silica sulfuric acid (SSA). The desired products are obtained in good to high yields without any toxic byproducts.

A general methodology for the synthesis of substituted phenols from pyranone precursors

Phenols are an important group of organic compounds,1 with many natural products such as polyketides, coumarins and flavonoids containing mono- or poly-phenolic moieties. The synthesis of substituted phenols from pyranone precursors is presented. A variety of pronucleophiles were used in combination with tert-butanol as solvent and potassium tert-butoxide as base, using both conventional heating methods and microwave conditions. Copyright

The Room-Temperature Palladium-Catalyzed Cyanation of Aryl Bromides and Iodides with Tri-t-butylphosphine as Ligand

The palladium-catalyzed cyanation of aryl bromides and iodides to the corresponding nitriles occurs at room temperature when tri-t-butylphosphine is used as ligand, Zn(CN)2 as the cyanide source and Zn dust as a co-catalyst in DMF as solvent. A variety of aromatic halides, including electron-withdrawing and electron-donating, can be efficiently cyanated under these conditions. The reactions are completed in less than 1 hour and products are produced in good to excellent yield.