52805-46-6

Basic information

• Product Name: 3-Hydroxy-4-methoxybenzonitrile
• Synonyms: ISOVANILLONITRILE;CBI-BB ZERO/005397;3-HYDROXY-4-METHOXYBENZONITRILE;3-HYDROXY-4-METHOXYBENZONITRILE (ISOVANILLONITRILE);3-Hydroxy-4-methoxybenzonitril;Benzonitrile, 3-hydroxy-4-Methoxy-;5-Cyano-2-methoxyphenol;Gefitinib IMpurity (3-Hydroxy-4-Methoxybenzonitrile)
• CAS NO: 52805-46-6
• Molecular Formula: C₈H₇NO₂
• Molecular Weight: 149.15
• Product Categories: Aromatic Nitriles;Gefitinib
• Mol File: 52805-46-6.mol
• Article Data: 26

Chemical Properties

• Boiling Point: 300.8 °C at 760 mmHg
• Flash Point: 135.7 °C
• Appearance: /
• Density: 1.24 g/cm³
• Vapor Pressure: 0.000613mmHg at 25°C
• Refractive Index: 1.568
• Storage Temp.: Inert atmosphere,Room Temperature
• PKA: 8.59±0.10(Predicted)
• CAS DataBase Reference: 3-Hydroxy-4-methoxybenzonitrile(CAS DataBase Reference)
• NIST Chemistry Reference: 3-Hydroxy-4-methoxybenzonitrile(52805-46-6)
• EPA Substance Registry System: 3-Hydroxy-4-methoxybenzonitrile(52805-46-6)

Safety Data

• Hazardous Substances Data: 52805-46-6(Hazardous Substances Data)

Usage

General Description

3-Hydroxy-4-methoxybenzonitrile, also known as Vanillonitrile or 3-Methoxy-4-hydroxybenzonitrile, is a chemical compound often used in various industries particularly in laboratory settings for experimentation or for certain chemical reactions. Its molecular formula is C8H7NO2. It belongs to the benzonitriles chemical group, which is characterized by a benzene ring bonded to a cyano group. This substance is classified under aromatic homomonocyclic compounds. It is generally a solid and displays a light yellow color. Its handling should be done carefully taking safety precautions, as exposure can cause skin and eye irritation.

InChI:InChI=1/C8H7NO2/c1-11-8-3-2-6(5-9)4-7(8)10/h2-4,10H,1H3

Upstream product

• 636-93-1 5-nitroguaiacol 
• 52805-37-5 3-benzyloxy-4-methoxybenzonitrile 
• 2024-83-1 veratronitrile 
• 831222-65-2 tert-butyl-(2-methoxy-5-vinylphenoxy)dimethylsilane 
• 874-90-8 4-methoxybenzonitrile 
• 621-59-0 isovanillin 
• 141-53-7 sodium formate 
• 51673-94-0 3-hydroxy-4-methoxy-benzaldehyde (E)-oxime 
• 2150-38-1 methyl 3,4-dimethoxybenzoate 
• 859767-02-5 3-acetoxy-4-methoxy-benzonitrile 
• 6346-05-0 3-benzyloxy-4-methoxybenzaldehyde 

Downstream Products

• 3147-34-0 3-<5-Cyan-2-methoxy-phenyl>-propylbromid 
• 93758-09-9 1,2,3,4,6,7,8,9-octahydro-1,6-dioxo-2-methyl-5-(2-methoxy-5-cyanophenoxy)-9-carbomethoxyisoquinoline 
• 93758-08-8 1,2,3,4,6,7,8,9-octahydro-1,6-dioxo-2-methyl-5-(2-methoxy-5-cyanophenoxy)-9-carbethoxyisoquinoline 
• 93757-86-9 1,2,3,4,6,7,8,9-octahydro-2,9-dicarbomethoxy-5-(2-methoxy-5-cyanophenoxy)-6-oxoisoquinoline 
• 78388-71-3 3-(3-Allyl-2-methyl-6-oxo-cyclohex-1-enyloxy)-4-methoxy-benzonitrile 
• 183307-05-3 3-[(3,5,6-trifluoro-4-methylpyridin-2-yl)oxy]-4-methoxybenzonitrile 
• 106662-35-5 3-allyloxy-4-methoxy-benzonitrile 
• 850856-55-2 2-bromo-5-hydroxy-4-methoxy-benzonitrile 
• 850856-57-4 2-bromo-3-hydroxy-4-methoxy-benzonitrile 
• 645-08-9 Isovanillic acid 
• 89702-89-6 5-(aminomethyl)-2-methoxyphenol 
• 192869-56-0 5-benzyloxy-4-methoxy-2-nitro-benzonitrile 
• 17345-61-8 3,4-dihydroxybenzonitrile 

Relevant articles and documents

Design, synthesis, and antitumor activity of novel quinazoline derivatives

In an attempt to explore a new class of epidermal growth factor receptor (EGFR) inhibitors, novel 4-stilbenylamino quinazoline derivatives were synthesized through a Dimorth rearrangement reaction and characterized via IR, 1H-NMR, 13C-NMR, and HRMS. Methoxyl, methyl, halogen, and trifluoromethyl groups on stilbeneamino were detected. These synthesized compounds were evaluated for antitumor activity in vitro against eight human tumor cell lines with an MTS assay. Most synthesized compounds exhibited more potent activity (IC50 = ~2.0 μM) than gefitinib (IC50 > 10.0 μM) against the A431, A549, and BGC-823 cell lines. Docking methodology of compound 6c and 6i binding into the ATP site of EGFR was carried out. The results showed that fluorine and trifluoromethyl played an important role in efficient cell activity.

Method for promoting iron-catalyzed oxidation of aromatic compound carbon - hydrogen bond to synthesize phenol by ligand

The method comprises the following steps: iron is used as - a catalyst metal; a sulfur-containing amino acid or cystine-derived dipeptide is a ligand; and under the common action of hydrogen peroxide as an oxidizing agent, an aromatic compound is synthesized to prepare a phenol. Under the action of an acid as an accelerant and hydrogen peroxide as an oxidizing agent, the aryl carbon - hydrogen bond is directly hydroxylated to form a phenolic compound, and the method for preparing the phenol by the catalytic oxidation reaction has a plurality of advantages. The reaction raw materials, the oxidant and the promoter are wide in source, low in price, environment-friendly and good in stability. The aromatic compound carbon - hydrogen bonds directly participate in the reaction to react in one step to form phenol. The reaction condition is mild, the functional group compatibility and the application range are wide. The reaction selectivity is good; under the optimized reaction conditions, the target product separation yield can reach 85%.

Preparation method of high-purity gefitinib key intermediate

The invention belongs to the field of drug synthesis, and particularly relates to a preparation method of a high-purity gefitinib key intermediate 6-hydroxy-7-methoxy-3H-quinazoline-4-ketone. The synthesis method is simple to operate, the yield is high, t