6587-24-2

Usage

Uses

Used in the Food Industry:
METHYL 2-CYANOBENZOATE is used as a flavoring agent for its distinctive floral scent, enhancing the taste and aroma of various food products.
Used in Pharmaceutical Production:
METHYL 2-CYANOBENZOATE is used as an intermediate in the synthesis of pharmaceuticals, contributing to the development of new medications.
Used in Agrochemical Production:
METHYL 2-CYANOBENZOATE is utilized as an intermediate in the production of agrochemicals, playing a role in the creation of substances that contribute to agricultural productivity and pest control.
Safety Precautions:
When handling METHYL 2-CYANOBENZOATE, it is used with caution due to its skin and eye irritant properties. Proper safety protocols are followed, including the use of personal protective equipment and ensuring well-ventilated workspaces to minimize exposure risks.

InChI:InChI=1/C9H7NO2/c1-12-9(11)8-5-3-2-4-7(8)6-10/h2-5H,1H3

Upstream product

• 134-20-3 2-carbomethoxyaniline 
• 57031-51-3 Methyl-tert.-butylperoxyoxalat 
• 100-47-0 benzonitrile 
• 610-97-9 o-iodo-methyl-benzoic acid 
• 151-50-8 potassium cyanide 
• 544-92-3 copper(I) cyanide 
• 88-97-1 phthalamic acid 
• 79-22-1 methyl chloroformate 
• 67-56-1 methanol 
• 95667-98-4 methyl 2-((methylsulfonyl)oxy)benzoate 
• 610-94-6 2-bromobenzoic acid methyl ester 
• 610-96-8 methyl chlorobenzoate 
• 557-21-1 dicyanozinc 
• 74-88-4 methyl iodide 

Downstream Products

• 55-21-0 benzamide 
• 1159-86-0 o-dibenzoylbenzene 
• 480-91-1 oxisoindole 
• 4122-56-9 methyl o-formylbenzoate 
• 26487-08-1 2-cyano-N,N-dimethylbenzamide 
• 76010-56-5 methyl 2-<3-(4-chlorophenyl)-1,2,4-thiadiazol-5-yl>-benzoate 
• 17174-98-0 o-cyanobenzamide 
• 14352-51-3 3-iminoisoindolinone 
• 3839-22-3 2-cyanobenzoic acid 
• 39519-11-4 isoindole-1,3-dione mono-dimethylhydrazone 
• 14257-08-0 isoindole-1,3-dione mono-phenylhydrazone 
• 40227-55-2 4-amino-2-methylphthalazin-1(2H)-one 
• 93616-63-8 3-(Benzyl-hydrazono)-2,3-dihydro-isoindol-1-one 
• 93616-64-9 3-[(1-Phenyl-ethyl)-hydrazono]-2,3-dihydro-isoindol-1-one 

Relevant academic research and scientific papers

Visible-Light-Promoted Metal-Free Synthesis of (Hetero)Aromatic Nitriles from C(sp3)?H Bonds**

The metal-free activation of C(sp3)?H bonds to value-added products is of paramount importance in organic synthesis. We report the use of the commercially available organic dye 2,4,6-triphenylpyrylium tetrafluoroborate (TPP) for the conversion of methylarenes to the corresponding aryl nitriles via a photocatalytic process. Applying this methodology, a variety of cyanobenzenes have been synthesized in good to excellent yield under metal- and cyanide-free conditions. We demonstrate the scope of the method with over 50 examples including late-stage functionalization of drug molecules (celecoxib) and complex structures such as l-menthol, amino acids, and cholesterol derivatives. Furthermore, the presented synthetic protocol is applicable for gram-scale reactions. In addition to methylarenes, selected examples for the cyanation of aldehydes, alcohols and oximes are demonstrated as well. Detailed mechanistic investigations have been carried out using time-resolved luminescence quenching studies, control experiments, and NMR spectroscopy as well as kinetic studies, all supporting the proposed catalytic cycle.

Acyl Cyanides as Bifunctional Reagent: Application in Copper-Catalyzed Cyanoamidation and Cyanoesterification Reaction

Cu-catalyzed domino decyanation and cyanation reaction of acyl cyanides with amines or alcohols have been developed. The cyano sources were generated in situ via C-CN cleavage yielding the corresponding cyano substituted amides or esters in moderate to excellent yields. This approach features a cheap copper catalyst, domino decyanation and cyanation reaction, readily available starting materials, broad substrate scope, operational simplicity, and the potential for further transformation of the cyano group.

Ligand-Promoted Non-Directed C?H Cyanation of Arenes

This article reports the first example of a 2-pyridone accelerated non-directed C?H cyanation with an arene as the limiting reagent. This protocol is compatible with a broad scope of arenes, including advanced intermediates, drug molecules, and natural products. A kinetic isotope experiment (kH/kD=4.40) indicates that the C?H bond cleavage is the rate-limiting step. Also, the reaction is readily scalable, further showcasing the synthetic utility of this method.

Continuous-Flow Pd-Catalyzed Carbonylation of Aryl Chlorides with Carbon Monoxide at Elevated Temperature and Pressure

The development of a continuous-flow protocol for a palladium-catalyzed methoxycarbonylation of (hetero)aryl chlorides using carbon monoxide gas and methanol is described. (Hetero)aryl chlorides are the least expensive of the aryl halides, but are underutilized in carbonylation reactions due to their very poor reactivity. The described protocol exploits intensified conditions at elevated temperature and pressure, which are readily accessed within a continuous-flow environment, to provide moderate to excellent product yields (11 examples) in a short 16 min residence time. The continuous-flow protocol enables the safe and potentially scalable carbonylation of aryl chlorides using CO gas.

Methyl esters of 2-(N-hydroxycarbamimidoyl)benzoyl-substituted α-amino acids as promising building blocks in peptidomimetic synthesis: a comparative study

Abstract: An efficient and simple synthetic protocol for the synthesis of a number methyl esters of 2-(N-hydroxycarbamimidoyl)benzoyl-substituted (S)-α-amino acids via subsequent coupling and hydroxyamination of 2-cyanobenzamide derivatives has been developed. Comparative analysis of three pseudopeptide series based on 2-cyano- and 2-amidoxime-substituted benzoic acid and its pyridine and pyrazine counterparts has been provided and it has revealed a practical advantage of the benzoic acid derivatives due to their greater availability. The impact of the nitrogen atom in the aromatic ring on the trans/cis-amide equilibrium in the proline derivatives is discussed. Graphical abstract: [Figure not available: see fulltext.]

Metal-free radical aromatic carbonylations mediated by weak bases

We report a new method of metal-free alkoxycarbonylation. This reaction involves the generation of aryl radicals from arenediazonium salts by a very weak base (HCO2Na) under mild conditions. Subsequent radical trapping with carbon monoxide and alcohols gives alkyl benzoates. The conditions (metal-free, 1 equiv. base, MeCN, r.t., 3 h) tolerate various functional groups (I, Br, Cl, CF3, SF5, NO2, ester). Mechanistic studies indicate the operation of a radical aromatic substitution mechanism.

Synthesis and evaluation of novel azoles as potent antifungal agents

Using a rational approach to the design of antifungal agents, a series of azole agents with 1,3,4-oxadiazole side chains were designed and synthesized. The results of preliminary in vitro antifungal tests with eight human pathogenic compounds showed that all of the title compounds exhibited excellent activities against all of the tested fungi except Aspergillus fumigatus. Compounds 11e and 11f were found to be the most effective, with a minimum inhibitory concentration of 0.0039 μg/mL, followed by voriconazole, which has a MIC of 0.0625 μg/mL. The 1,3,4-oxadiazole side chain is not the major contributor but plays a role in eliciting the observed antifungal activity.

A highly efficient, ligand-free and recyclable SBA-15 supported Cu 2O catalyzed cyanation of aryl iodides with potassium hexacyanoferrate(ii)

SBA-15 supported Cu2O nanoparticles (Cu2O/SBA-15) have been fabricated and characterized. The as-prepared Cu2O/SBA-15 is a highly effective catalyst for cyanation of aryl iodides using non-toxic K4[Fe(CN)6] as a cyanide source in dimethylformamide (DMF). The approach achieves a high selectivity and an excellent yield without using any ligands and base additives. Moreover, the Cu2O/SBA-15 catalyst shows wide functional group tolerance and reusability with a slight loss of activity. the Partner Organisations 2014.

Skeletal rearrangement of cyano-substituted iminoisobenzofurans into alkyl 2-cyanobenzoates catalyzed by B(C6F5)3

An efficient method for the direct conversion of cyano-substituted iminoisobenzofurans into their corresponding alkyl 2-cyanobenzoates has been developed. This transformation proceeds via cleavage of C-C, C-O, and C-N bonds in starting iminoisobenzofurans. DFT study revealed that intermediate α-iminonitriles are produced in situ via C-C bond formation between 2-iminium benzoates and a cyanide ion. Generation of isocyanide as the byproduct in a more thermodynamic manner in DFT calculations also supports the experimental results.

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.