43020-38-8

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Chemical Properties

WHITE NEEDLES

InChI:InChI=1/C10H11NO3/c1-12-8-5-4-7(6-11)9(13-2)10(8)14-3/h4-5H,1-3H3

Upstream product

• 79068-56-7 2-Imino-5-(2,3,4-trimethoxyphenyl)thiazolidin-4-on 
• 2103-57-3 2,3,4-trimethoxybenzaldehyde 
• 22480-91-7 (2,3,4-trimethoxy-phenyl)-acetic acid 
• 4885-02-3 Dichloromethyl methyl ether 
• 634-36-6 1,2,3-trimethoxybenzene 
• 25245-37-8 1-iodo-2,3,4-trimethoxy-benzene 
• 84-58-2 2,3-dicyano-5,6-dichloro-p-benzoquinone 
• 57-13-6 urea 
• 1111-67-7 copper(I) thiocyanate 
• 93-61-8 N-methyl-N-phenylformamide 
• 68-12-2 N,N-dimethyl-formamide 
• 79068-57-8 DL-Mercapto(2,3,4-trimethoxyphenyl)essigsaeure 
• 79068-55-6 DL-2,2,2-Trichlor(2,3,4-trimethoxyphenyl)ethanol 
• 3012-37-1 benzyl thiocyanate 

Downstream Products

• 1123268-57-4 6-iodo-2,3,4-trimethoxybenzonitrile 
• 41219-16-3 2,3,4-trimethoxybenzylamine 
• 573-11-5 2,3,4-Trimethoxy-benzoic acid 
• 18060-58-7 2,3,4-trimethoxypropiophenone 

Relevant academic research and scientific papers

Direct Carbon Isotope Exchange of Pharmaceuticals via Reversible Decyanation

The incorporation of carbon-14 allows tracking of organic molecules and provides vital knowledge on their fate. This information is critical in pharmaceutical development, crop science, and human food safety evaluation. Herein, a transition-metal-catalyzed procedure enabling carbon isotope exchange on aromatic nitriles is described. By utilizing the radiolabeled precursor Zn([14C]CN)2, this protocol allows the insertion of the desired carbon tag without the need for structural modifications, in a single step. By reducing synthetic costs and limiting the generation of radioactive waste, this procedure will facilitate the labeling of nitrile containing drugs and accelerate 14C-based ADME studies supporting drug development.

CuO-catalyzed conversion of arylacetic acids into aromatic nitriles with K4Fe(CN)6 as the nitrogen source

Readily available CuO was demonstrated to be effective as the catalyst for the conversion of arylacetic acids to aromatic nitriles with non-toxic and inexpensive K4Fe(CN)6 as the nitrogen source via the complete cleavage of the C[tbnd]N triple bond. The present method allowed a series of arylacetic acids including phenylacetic acids, naphthaleneacetic acids, 2-thiopheneacetic acid and 2-furanacetic acid to be converted into the targeted products in low to high yields.

Iron and Phenol Co-Catalysis for Rapid Synthesis of Nitriles under Mild Conditions

A mild, scalable, high yielding, and rapid route to access diverse nitriles from aldehyde oxime esters enabled by iron(III) and phenol co-catalysis has been developed. The reaction was performed at room temperature to give nitriles in excellent yield within minutes. Mechanistic studies show that the reaction may proceed through a radical process in which benzoyl aldehyde oxime is not only a substrate, but also an ancillary ligand to support iron salt in the promotion of the transformation.

Method for preparing nitrile

The invention provides a method for preparing nitrile. Aldoxime carboxylic ester is used as a reactant to prepare a nitrile compound. The aldoxime carboxylic ester can be completely converted into corresponding nitrile under common catalysis of ferric salt and phenol within a few minutes. The method for preparing the nitrile has the advantages of gentle reaction conditions, simple and easy-to-getused reagents, cheap and environment-friendly catalyst, wide substrate application range, simple operation, rapid reaction and the like.

Stable and reusable nanoscale Fe2O3-catalyzed aerobic oxidation process for the selective synthesis of nitriles and primary amides

The sustainable introduction of nitrogen moieties in the form of nitrile or amide groups in functionalized molecules is of fundamental interest because nitrogen-containing motifs are found in a large number of life science molecules, natural products and materials. Hence, the synthesis and functionalization of nitriles and amides from easily available starting materials using cost-effective catalysts and green reagents is highly desired. In this regard, herein we report the nanoscale iron oxide-catalyzed environmentally benign synthesis of nitriles and primary amides from aldehydes and aqueous ammonia in the presence of 1 bar O2 or air. Under mild reaction conditions, this iron-catalyzed aerobic oxidation process proceeds to synthesise functionalized and structurally diverse aromatic, aliphatic and heterocyclic nitriles. Additionally, applying this iron-based protocol, primary amides have also been prepared in a water medium.

Facile one-pot transformation of arenes into aromatic nitriles under metal-cyanide-free conditions

Electron-rich arenes bearing methyl or methoxy groups on the aromatic ring were treated with dichloromethyl methyl ether and ZnBr2, and then with molecular iodine and aq. ammonia to give the corresponding aromatic nitriles in good yields. Using this method, febuxostat was efficiently prepared from 4-bromophenol in four steps. The method can be used for the preparation of aromatic nitriles from arenes in one pot under metal-cyanide-free conditions. Various electron-rich arenes could be effectively converted into the corresponding aromatic nitriles in good yields, by treatment with ZnBr2 and dichloromethyl methyl ether, followed by reaction with molecular iodine and aq. ammonia.

Utility of Nitrogen Extrusion of Azido Complexes for the Synthesis of Nitriles, Benzoxazoles, and Benzisoxazoles

The utility of the nitrogen extrusion reaction of azido complexes, generated in situ from the corresponding aldehydes or ketones with TMSN3 in the presence of ZrCl4 or TfOH, has been described. These azido complexes could undergo three different pathways, depending on the substrates. First, azido methanolate complexes or imine diazonium ions could lead to benzisoxazole products via an intramolecular nucleophilic substitution. Second, imine diazonium ions could also undergo either the elimination of proton to provide nitrile products in good to excellent yields or an aryl migration, followed by an intramolecular nucleophilic addition, to give benzoxazole products in good yields.

Catalytic cyanation of aryl iodides using DMF and ammonium bicarbonate as the combined source of cyanide: A dual role of copper catalysts

Cu(ii)-catalyzed cyanation of aryl iodides has been developed using DMF and ammonium bicarbonate as the combined source of cyanide. It is assumed that copper is involved both in the generation of CN units from DMF-ammonia and in the cyanation of aryl halides. A range of electron-rich and fused (hetero)aryl iodides underwent cyanation resulting in moderate to good yields.

Copper- and silver-mediated cyanation of aryl iodides using ddq as cyanide source

A new copper and silver-mediated cyanation of aryl iodides with DDQ as a cyanide source is achieved, providing nitriles with good yields. This new approach represents a safe method leading to aryl nitriles. A new copper and silver-mediated cyanation of aryl iodides with DDQ as a cyanide source is achieved.

Copper-catalyzed cyanation of aryl iodide with the combined cyanide source of urea and DMSO

A simple copper-catalyzed cyanation of aryl iodide with the combination of urea and dimethyl sulfoxide as a cyanide source is achieved, providing nitriles in moderate to good yields. This new approach represents an exceedingly practical and safe method for the synthesis of aryl nitriles.