4468-59-1

Usage

Uses

Used in Pharmaceutical Industry:
4-Hydroxy-3-methoxyphenylacetonitrile is used as a pharmaceutical compound for its potential therapeutic properties. 4-HYDROXY-3-METHOXYPHENYLACETONITRILE's unique structure may allow it to interact with biological targets, making it a candidate for the development of new drugs or therapies.
Used in Chemical Synthesis:
4-Hydroxy-3-methoxyphenylacetonitrile can be used as a starting material or intermediate in the synthesis of various organic compounds. Its unique functional groups make it a versatile building block for creating a wide range of molecules with different applications.
Used in Research and Development:
As a naturally occurring compound with unique properties, 4-Hydroxy-3-methoxyphenylacetonitrile can be used in research and development to study its chemical behavior, reactivity, and potential applications in various fields.
Used in Analytical Chemistry:
4-HYDROXY-3-METHOXYPHENYLACETONITRILE can be used as a reference material or standard in analytical chemistry for the development and validation of analytical methods, such as high-performance liquid chromatography (HPLC) or mass spectrometry (MS), for the identification and quantification of similar compounds in complex samples.

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

• 1239584-73-6 C₂₃H₃₁NO₃ 
• 93-51-6 2-Methoxy-4-methylphenol 

Relevant academic research and scientific papers

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.

Novel phenolic glycosides, adenophorasides A-E, from Adenophora roots

Five novel phenolic glycosides, adenophorasides A (1), B (2), C (3), D (4), and E (5), were isolated from commercial Adenophora roots, together with vanilloloside (6), 3,4-dimethoxybenzyl alcohol 7-O-β-D-glucopyranoside (7), and lobetyolin (8). The structures of the new compounds (1-5) were characterized as 4-hydroxy-3-methoxyphenylacetonitrile 4-O-β-D- glucopyranoside (1), 4-hydroxy-3-methoxyphenylacetonitrile 4-O-β-D- glucopyranosyl-1→6)-b-D-glucopyranoside (2), 4-hydroxy-3- methoxyphenylacetonitrile 4-O-α-L-rhamnopyranosyl-(1→6)-β-D- glucopyranoside (3), 4-hydroxyphenylacetonitrile 4-O-β-D-glucopyranosyl- (1→6)-β-D-glucopyranoside (4),and 4-hydroxy-3-methoxybenzyl alcohol 4-O-β-D-glucopyranosyl-(1→6)-β-D-glucopyranoside (5), respectively, by means of spectroscopic and chemical analyses. The Japanese Society of Pharmacognosy and Springer 2010.

The palladium-catalyzed preparation of condensed tetracyclic heterocycles and their application to the synthesis of rac-mangochinine

Dihydroisoquinoline derivatives and their analogues, prepared by the Bischler-Napieralsky reaction, were converted to their indole-fused derivatives. Scope and limitations of the palladium-catalyzed reaction, proceeding through the tautomeric enamine forms of these compounds, were studied and the process was extended to the preparation of racemic mangochinine. Georg Thieme Verlag Stuttgart.

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.

Degradation of 3-aryl-2-hydroxyiminopropionic acids into arylacetonitriles using 1,1'-carbonyldiimidazole or 2,2'-oxalyldi(o-sulfobenzimide)

1,1'-Carbonyldiimidazole (1) is a useful reagent for the preparation of arylacetonitriles (9) from 3-aryl-2-hydroxyiminopropionic acids (8), and 2,2'-oxalyldi (o-sulfobenzimide) (2) can also be used for this purpose under essentially neutral conditions.

SYNTHESES BASED ON β-PHENYLETHYLAMINES. I. PREPARATION OF SUBSTITUTED β-PHENYLETHYLAMINES

A comparative study has been made of methods of synthesizing substituted β-phenylethylamines via the corresponding nitriles and via nitrostyrenes, and a superiority of the latter method has been established.The possibility has been shown for the first time of reducing nitrostyrenes to saturated amines with diisobutylaluminum hydride (DIBAH).The use of DIBAH as reducing agent enables amines to be obtained in high yields.

Process for the manufacture of aromatic cyanides

The invention provides a process for the preparation of ortho- and para-hydroxybenzyl cyanides. The process of the invention comprises the reaction of an aromatic alcohol selected from ortho- and para-hydroxybenzyl alcohols with a cyanide reagent and an ester capable of esterifying the hydroxyl group of the benzyl alcohol. In a preferred form of the process there is employed a route via the reaction of an ortho- or para-hydroxybenzyl formate with a cyanide reagent preferably selected from sodium and potassium cyanides.