14894-77-0

Basic information

• Product Name: 2,4,5-TRIMETHOXYBENZONITRILE
• Synonyms: 2,4,5-TRIMETHOXYBENZONITRILE;Benzonitrile,2,4,5-triMethoxy-
• CAS NO: 14894-77-0
• Molecular Formula: C₁₀H₁₁NO₃
• Molecular Weight: 193.2
• Product Categories: Aromatic Nitriles
• Mol File: 14894-77-0.mol

Chemical Properties

• Melting Point: 112-114°C
• Boiling Point: 333.8 °C at 760 mmHg
• Flash Point: 139.4 °C
• Appearance: /
• Density: 1.15 g/cm³
• Vapor Pressure: 0.000133mmHg at 25°C
• Refractive Index: 1.514
• CAS DataBase Reference: 2,4,5-TRIMETHOXYBENZONITRILE(CAS DataBase Reference)
• NIST Chemistry Reference: 2,4,5-TRIMETHOXYBENZONITRILE(14894-77-0)
• EPA Substance Registry System: 2,4,5-TRIMETHOXYBENZONITRILE(14894-77-0)

Safety Data

• Hazardous Substances Data: 14894-77-0(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
2,4,5-Trimethoxybenzonitrile is used as a building block in organic synthesis for the production of various pharmaceuticals and agrochemicals. Its unique structure allows for the creation of a wide range of compounds with potential therapeutic and pesticidal properties.
Used in Dye Manufacturing:
In the dye industry, 2,4,5-Trimethoxybenzonitrile is utilized in the manufacturing of dyes and other specialty chemicals. Its chemical properties contribute to the development of dyes with specific color characteristics and stability.
Used in Pharmaceutical Industry:
2,4,5-Trimethoxybenzonitrile is used as an intermediate in the synthesis of pharmaceuticals. Its presence in the molecular structure of certain drugs can enhance their efficacy and pharmacological properties.
Used in Agrochemical Industry:
In the agrochemical sector, 2,4,5-Trimethoxybenzonitrile is employed in the development of agrochemicals, such as pesticides and herbicides. Its incorporation into these products can improve their effectiveness in controlling pests and weeds.
Used in Biological Research:
2,4,5-Trimethoxybenzonitrile has been studied for its potential biological activities, including anticancer and antifungal properties. Researchers are investigating its precise mechanism of action and potential toxicity to better understand its therapeutic potential.

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

Upstream product

• 506-68-3 bromocyane 
• 135-77-3 1,2,4-trimethoxy-benzene 
• 4424-79-7 2,4,5-trimethoxybenzamide 
• 2880-58-2 2-methoxy-1,4-benzoquinone 
• 151-50-8 potassium cyanide 
• 77-78-1 dimethyl sulfate 
• 75-15-0 carbon disulfide 
• 7446-70-0 aluminium trichloride 
• 42833-66-9 2,4,5-trimethoxybenzoyl chloride 
• 490-64-2 asaronic acid 
• 931-97-5 1-hydroxy-1-cyclohexanecarbonitrile 
• 23149-33-9 1-iodo-2,4,5-trimethoxybenzene 
• 68-12-2 N,N-dimethyl-formamide 
• 67-56-1 methanol 

Relevant articles and documents

Organic semiconductor photocatalyst can bifunctionalize arenes and heteroarenes

Photoexcited electron-hole pairs on a semiconductor surface can engage in redox reactions with two different substrates. Similar to conventional electrosynthesis, the primary redox intermediates afford only separate oxidized and reduced products or, more rarely, combine to one addition product. Here, we report that a stable organic semiconductor material, mesoporous graphitic carbon nitride (mpg-CN), can act as a visible-light photoredox catalyst to orchestrate oxidative and reductive interfacial electron transfers to two different substrates in a two- or three-component system for direct twofold carbon–hydrogen functionalization of arenes and heteroarenes. The mpg-CN catalyst tolerates reactive radicals and strong nucleophiles, is straightforwardly recoverable by simple centrifugation of reaction mixtures, and is reusable for at least four catalytic transformations with conserved activity.

Development of Decarboxylative Cyanation Reactions for C-13/C-14 Carboxylic Acid Labeling Using an Electrophilic Cyanating Reagent

Degradation-reconstruction approaches for isotope labeling synthesis have been known for their remarkable efficiency, but applications are scarce due to some fundamental limitations of the chemistries developed to date. The decarboxylative cyanation reaction, as a degradation-reconstruction approach, is especially useful in rapid carboxylic acid carbon isotope labeling, however development toward its application as a widespread technique has stalled at the early stages due to numerous limitations which include somewhat narrow applicability. Employing the electrophilic cyanating reagent N-cyano-N-phenyl-p-toluenesulfonamide (NCTS) as the cyano source, efficient decarboxylative cyanation chemistry has been developed for aryl and alkyl carboxylic acids respectively with two rationally designed reaction pathways. The reactions provided good yields of nitrile products from carboxylic acids, with complete retention of isotopic purity from the [13CN]-NCTS used. The reaction conditions are relatively mild requiring no oxidant and no excess toxic heavy metal and the reagent [13/14CN]-NCTS is a stable, easy-to-handle crystalline solid that can be prepared quickly and effectively from the readily available [13/14C]-KCN. The following work describes this novel and efficient method for alkyl and aryl carboxylic acid isotopic labeling using a single reagent.

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.

Palladium-catalyzed cyanation of aryl halides with CuSCN

A palladium-catalyzed cyanation of aryl halides and borons has been developed by employing cuprous thiocyanate as a safe cyanide source. This protocol avoids the use of a highly toxic cyanide source, providing aromatic nitriles in moderate to good yields with good functional tolerance.

Copper-mediated sequential cyanation of aryl C-B and arene C-H bonds using ammonium iodide and DMF

The cyanation of aromatic boronic acids, boronate esters, and borate salts was developed under copper-mediated oxidative conditions using ammonium iodide and DMF as the source of nitrogen and carbon atom of the cyano unit, respectively. The procedure was successfully extended to the cyanation of electron-rich benzenes, and regioselective introduction of a cyano group at the arene C-H bonds was also achieved. The observation that the reaction proceeds via a two-step process, initial iodination and then cyanation, led us to propose that ammonium iodide plays a dual role to provide iodide and nitrogen atom of the cyano moiety.

Pd(OAc)2-catalyzed alkoxylation of arylnitriles via sp 2 C-H bond activation using cyano as the directing group

A Pd(OAc)2-catalyzed ortho-alkoxylation of arylnitrile was described. Using cyano as a directing group, the aromatic C-H bond can be functionalized efficiently to generate ortho-alkoxylated arylnitrile derivatives with moderate yields. The opti

Iron-mediated cyanation of methoxybenzene, indole, and 2-arylpyridine C-H bonds

An iron-mediated direct cyanation of indole and 2-arylpyridine C-H bonds is described. Notably, trimethoxybenzene reacted smoothly under the procedure, forming a C-CN bond via C-H bond cleavage without chelation assistance. Georg Thieme Verlag Stuttgart · New York.

Copper-mediated cyanation of aryl halide with the combined cyanide source

A simple copper-mediated cyanation of aryl halide with the combination of ammonium bicarbonate and N,N-dimethylformamide 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.

Straightforward conversion of arene carboxylic acids into aryl nitriles by palladium-catalyzed decarboxylative cyanation reaction

A one-pot procedure to convert aromatic carboxylic acids into aromatic nitriles is described. The methodology is based on a palladium(II)-catalyzed decarboxylative cyanation reaction using cyanohydrins as soluble cyanide sources. The described reaction worked on a panel of substrates and is additionally of particular interest for the straightforward preparation of 13C- or 14C-labeled compounds.

Evaluation of some preparations of trialkoxyphthalic acid derivatives

Several approaches to trialkoxyphthalic acid derivatives, potential intermediates in a fredericamycin synthesis, were tested. Sequences based on a Diels-Alder/retro Diels-Alder reaction, a cyanide addition to a quinone, an Elbe oxidation, and an amide-directed ortho-lithiation are discussed in terms of length, yields, convenience, and the versatility of the product of each.