4468-59-1

Basic information

• Product Name: 4-HYDROXY-3-METHOXYPHENYLACETONITRILE
• Synonyms: HOMOVANILLONITRILE;4-HYDROXY-3-METHOXYPHENYLACETONITRILE;Homovanillonitrile (4-hydroxy-3-methoxy-phenyl)acetonitrile;4-HYDROXY-3-METHOXYPHENYLACETONITRILE, 9 9%;3-Methoxy-4-hydroxybenzeneacetonitrile;4-Hydroxy-3-methoxybenzeneacetonitrile;4-Hydroxy-3-methoxybenzyl cyanide;2-(4-Hydroxy-3-methoxyphenyl)acetonitrile
• CAS NO: 4468-59-1
• Molecular Formula: C₉H₉NO₂
• Molecular Weight: 163.17
• EINECS: 224-739-5
• Product Categories: Aromatic Nitriles;Building Blocks;C8 to C9;Chemical Synthesis;Cyanides/Nitriles;Nitrogen Compounds;Organic Building Blocks
• Mol File: 4468-59-1.mol
• Article Data: 12

Chemical Properties

• Melting Point: 56-57 °C(lit.)
• Boiling Point: 135-145 °C2 mm Hg(lit.)
• Flash Point: 153.1 °C
• Appearance: /
• Density: 1.2021 (rough estimate)
• Vapor Pressure: 0.000269mmHg at 25°C
• Refractive Index: 1.5270 (estimate)
• PKA: 9.69±0.18(Predicted)
• CAS DataBase Reference: 4-HYDROXY-3-METHOXYPHENYLACETONITRILE(CAS DataBase Reference)
• NIST Chemistry Reference: 4-HYDROXY-3-METHOXYPHENYLACETONITRILE(4468-59-1)
• EPA Substance Registry System: 4-HYDROXY-3-METHOXYPHENYLACETONITRILE(4468-59-1)

Safety Data

• Hazard Codes: Xn,Xi
• Statements: 20/21/22-36/37/38
• Safety Statements: 26-37/39
• WGK Germany: 3
• HazardClass: IRRITANT-HARMFUL
• Hazardous Substances Data: 4468-59-1(Hazardous Substances Data)

Usage

General Description

4-Hydroxy-3-methoxyphenylacetonitrile is a phenolic glycoside which is isolated from commercial Adenophora roots.

InChI:InChI=1/C9H9NO2/c1-12-9-6-7(4-5-10)2-3-8(9)11/h2-3,6,11H,4H2,1H3

Upstream product

• 4468-58-0 3-hydroxy-4-methoxyphenylacetonitrile 
• 5447-36-9 2-hydroxyimino-3-(4-hydroxy-3-methoxy-phenyl)-propionic acid 
• 1252085-63-4 4-hydroxy-3-methoxyphenylacetonitrile 4-O-α-L-rhamnopyranosyl(1->6)-β-D-glucopyranoside 
• 1252085-62-3 4-hydroxy-3-methoxyphenylacetonitrile 4-O-β-D-glucopyranosyl(1->6)-β-D-glucopyranoside 
• 1252085-61-2 4-hydroxy-3-methoxyphenylacetonitrile 4-O-β-D-glucopyranoside 
• 773837-37-9 sodium cyanide 
• 498-00-0 4-hydroxymethyl-2-methoxyphenol 
• 1058649-06-1 2-methoxy-4-((methoxymethoxy)methyl) phenol 
• 10442-39-4 tetra-n-butylammonium cyanide 
• 1058649-10-7 4-((ethoxymethoxy)methyl)-2-methoxy phenol 
• 121-33-5 vanillin 
• 93-17-4 3,4-dimethoxyphenylacetonitrile 
• 143-33-9 sodium cyanide 
• 5438-51-7 (4-acetoxy-3-methoxy-phenyl)-acetonitrile 

Downstream Products

• 93-51-6 2-Methoxy-4-methylphenol 
• 88449-50-7 2-(4-isopropoxy-3-methoxyphenyl)acetic acid 

Relevant articles and documents

Synthesis of N-benzyl-des-D-ring lamellarin K via an acyl-Claisen/Paal-Knorr approach

Lamellarin K is a complex pyrrole natural product and member of the lamellarin family – a group of natural products known for their potent biological activities, such as, antiproliferative activity and inhibition of P-gp mediated drug efflux pumps. We herein describe the synthesis of the N-benzyl-des-D ring analogue of lamellarin K using a route that centres on an acyl-Claisen reaction to eventually prepare a highly-functionalised 1-aryl-4-methyl-1,4-diketone. Paal-Knorr pyrrole formation using this diketone undergoes auto-oxidation to give a fully-substituted 5-formyl pyrrole which was converted into the natural lactone B ring. Antiproliferative testing of the N-benzyl-des-D ring analogue gave an IC50 of 2.63?μM against the MDA-MB-231 breast cancer cell line.

Microwave-promoted, one-pot conversion of alkoxymethylated protected alcohols into their corresponding nitriles, bromides, and iodides using [bmim][InCl4] as a green catalyst

The Lewis acid room temperature ionic liquid, [bmim][InCl4], was found to be an efficient and green catalyst for the highly chemoselective and one-pot conversion of MOM- or EOM-ethers into their corresponding nitriles, bromides, and iodides under microwave irradiation. The procedures are simple, rapid, and high yielding. The catalyst exhibited a remarkable reactivity and is reusable.

Syntheses of NAMDA derivatives inhibiting NO production in BV-2 cells stimulated with lipopolysaccharide

Sixteen derivatives of N-acetyl-3-O-methyldopamine (NAMDA), an inhibitor of BH4 synthesis, were designed and synthesized. The ability of these derivatives to inhibit NO and BH4 production by lipopolysaccharide- stimulated BV-2 microglial cells was determined. While NAMDA at 100 μM inhibited NO and BH4 production by only about 20%, its catecholamide 8, indole 23 derivative, 13, and N-acetyl tetrahydroisoquinoline 25 inhibited the NO production by >50% at the same concentration. In particular, 13 and 25 inhibited both NO and BH4 production to similar degrees, which suggested that these compounds might inhibit NO production by blocking BH 4-dependent dimerization of the newly synthesized iNOS monomer.