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

Downstream Products

• 3147-34-0 3-<5-Cyan-2-methoxy-phenyl>-propylbromid 
• 183307-50-8 3-[(6-(5-cyano-2-methoxyphenoxy)-3,5-difluoro-4-methylpyridin-2-yl)oxy]-N,N-dimethylbenzamide 
• 850856-55-2 2-bromo-5-hydroxy-4-methoxy-benzonitrile 
• 850856-57-4 2-bromo-3-hydroxy-4-methoxy-benzonitrile 
• 675126-28-0 4-methoxy-3-[3-(morpholin-4-yl)propoxy]benzonitrile 
• 183307-05-3 3-[(3,5,6-trifluoro-4-methylpyridin-2-yl)oxy]-4-methoxybenzonitrile 
• 17345-61-8 3,4-dihydroxybenzonitrile 
• 60758-86-3 3-ethoxy-4-methoxybenzenecarbonitrile 

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.

Iron-catalyzed arene C-H hydroxylation

The sustainable, undirected, and selective catalytic hydroxylation of arenes remains an ongoing research challenge because of the relative inertness of aryl carbon-hydrogen bonds, the higher reactivity of the phenolic products leading to over-oxidized by-products, and the frequently insufficient regioselectivity. We report that iron coordinated by a bioinspired L-cystine-derived ligand can catalyze undirected arene carbon-hydrogen hydroxylation with hydrogen peroxide as the terminal oxidant. The reaction is distinguished by its broad substrate scope, excellent selectivity, and good yields, and it showcases compatibility with oxidation-sensitive functional groups, such as alcohols, polyphenols, aldehydes, and even a boronic acid. This method is well suited for the synthesis of polyphenols through multiple carbon-hydrogen hydroxylations, as well as the late-stage functionalization of natural products and drug molecules.

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