13531-48-1

Usage

Uses

Used in Pharmaceutical Industry:
Methyl 3-cyanobenzoate is used as an intermediate for the synthesis of 3-Carbamoylbenzoic Acid Derivatives, which are known as inhibitors of Human Apurinic/Apyrimidinic Endonuclease 1 (APE1). These derivatives play a crucial role in the development of potential therapeutic agents for various diseases, including cancer and neurodegenerative disorders.
Used in Chemical Synthesis:
Methyl 3-cyanobenzoate is also used in the preparation of 3-[5-(2-Fluorophenyl)-1,2,4-oxadiazol-3-yl]benzoic Acid Sodium Salt (F596070), a compound with potential applications in various fields, such as pharmaceuticals, agrochemicals, and materials science. Its unique structure and reactivity make it a valuable building block for the development of new molecules with diverse properties and functions.

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

Upstream product

• 57031-51-3 Methyl-tert.-butylperoxyoxalat 
• 100-47-0 benzonitrile 
• 186581-53-3 diazomethane 
• 626-17-5 benzene-1,3-dicarbonitrile 
• 1877-72-1 3-Cyanobenzoic acid 
• 618-89-3 methyl 3-bromobenzoate 
• 544-92-3 copper(I) cyanide 
• 151-50-8 potassium cyanide 
• 618-91-7 methyl 3-iodo-benzoate 
• 67-56-1 methanol 
• 6952-59-6 3-cyanobromobenzene 
• 201230-82-2 carbon monoxide 
• 1711-11-1 3-cyanobenzoyl chloride 
• 106748-24-7 methyl 3-carbamoylbenzoate 

Downstream Products

• 98-86-2 acetophenone 
• 1877-71-0 benzene 1,3-dicarboxylic acid monomethyl ester 
• 148345-63-5 methyl 3-(1H-tetrazol-5-yl)benzoate 
• 106748-27-0 3-thiocarbamoyl-benzoic acid methyl ester 
• 93071-65-9 3-methoxycarbonyl benzylamine 
• 208450-86-6 di(3-methoxycarbonylphenylmethyl)amine 
• 775304-79-5 methyl (Z)-3-(N’-hydroxycarbamimidoyl)benzoate 
• 1141475-82-2 3-(N-hydroxyamidino)benzoic acid methyl ester 
• 180863-55-2 methyl 3-(((tert-butoxycarbonyl)amino)methyl)benzoate 
• 1141475-82-2 3-(N-hydroxycarbamimidoyl)-benzoic acid methyl ester 
• 125775-98-6 methyl 3-(4,6-bis(trichloromethyl)-s-triazin-2-yl)benzoate 
• 23568-85-6 3-cyano-2,2,2-trifluoroacetophenone 
• 34231-22-6 [3-(aminomethyl)phenyl]methanol 
• 1253889-47-2 N⁽¹⁾-(3,5-bis(trifluoromethyl)phenyl)-N⁽²⁾-(3-(hydroxymethyl)benzyl)phthalamide 

Relevant academic research and scientific papers

Discovery of 4-chloro-3-(5-(pyridin-3-yl)-1,2,4-oxadiazole-3-yl)benzamides as novel RET kinase inhibitors

A series of novel 4-chloro-benzamides derivatives containing substituted five-membered heteroaryl ring were designed, synthesized and evaluated as RET kinase inhibitors for cancer therapy. Most of compounds exhibited moderate to high potency in ELISA-based kinase assay. In particular, compound I-8 containing 1,2,4-oxadiazole strongly inhibited RET kinase activity both in molecular and cellular level. In turn, I-8 inhibited cell proliferation driven by RET wildtype and gatekeeper mutation. The results implied that 4-chloro-3-(5-(pyridin-3-yl)-1,2,4-oxadiazole-3-yl)benzamides are promising lead compounds as novel RET kinase inhibitor for further investigation.

Pyrazol-1, 2, 4-oxadiazole substituted benzamide compound as well as preparation method and application of pyrazol-1, 2, 4-oxadiazole substituted benzamide compound

The invention belongs to the technical field of chemical synthesis and medicine application, and particularly relates to a pyrazol-1, 2, 4-oxadiazole substituted benzamide compound as well as a preparation method and application of the pyrazol-1, 2, 4-oxadiazole substituted benzamide compound. The preparation method comprises the following steps: reacting methyl 3-cyanobenzoate with hydroxylamine hydrochloride to obtain an intermediate 3, then carrying out ring synthesis on the intermediate 3 and pyrazole acid to obtain pyrazol-1, 2, 4-oxadiazole substituted methyl benzoate, and finally carrying out hydrolysis and condensation to obtain the pyrazol-1, 2, 4-oxadiazole substituted benzamide compound. According to the present invention, the structure of the obtained product is confirmed through the nuclear magnetic hydrogen spectrum, the bactericidal activity test is performed on the obtained 18 target products, and the results show that the target product obtained through the preparation method has good antibacterial activity at the concentration of 50 ppm, and the inhibition rate on the rhizoctonia solani within 7 h can achieve 100%.

Synthesis, characterization, and biological evaluation of new derivatives targeting MbtI as antitubercular agents

Tuberculosis (TB) causes millions of deaths every year, ranking as one of the most dangerous infectious diseases worldwide. Because several pathogenic strains of Mycobacterium tuberculosis (Mtb) have developed resistance against most of the established anti-TB drugs, new therapeutic options are urgently needed. An attractive target for the development of new antitubercular agents is the salicylate synthase MbtI, an essential enzyme for the mycobacterial siderophore biochemical machinery, absent in human cells. A set of analogues of I and II, two of the most potent MbtI inhibitors identified to date, was synthesized, characterized, and tested to elucidate the structural requirements for achieving an efficient MbtI inhibition and a potent antitubercular activity with this class of compounds. The structure-activity relationships (SAR) here discussed evidenced the importance of the furan as part of the pharmacophore and led to the preparation of six new compounds (IV-IX), which gave us the opportunity to examine a hitherto unexplored position of the phenyl ring. Among them emerged 5-(3-cyano-5-(trifluoromethyl)phenyl)furan-2-carboxylic acid (IV), endowed with comparable inhibitory properties to the previous leads, but a better antitubercular activity, which is a key issue in MbtI inhibitor research. Therefore, compound IV offers promising prospects for future studies on the development of novel agents against mycobacterial infections.

Mild Copper-Catalyzed Addition of Arylboronic Esters to Di- tert -butyl Dicarbonate: An Easy Access to Methyl Arylcarboxylates

An efficient copper-catalyzed addition of arylboronic esters to (Boc) 2O was developed. The reaction can be conducted under exceedingly mild conditions and is compatible with a variety of synthetically relevant functional groups. It therefore represents a useful alternative route for the synthesis of methyl arylcarboxylates. A preliminary mechanistic study indicated the involvement of an addition-elimination mechanism.

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.

Photocatalytic Conversion of Benzyl Alcohols/Methyl Arenes to Aryl Nitriles via H-Abstraction by Azide Radical

This report presents the visible-light-assisted synthesis of aryl nitriles from easily accessible alcohols or methyl arenes in the presence of O2. Organic photoredox catalyst, 4CzIPN (1,2,3,5-tetrakis(carbazol-9-yl)-4,6-dicyanobenzene), induces single electron transfer (SET) from azide N3? and generates azide radical N3?.The photogenerated N3? abstracts H atom from α-C?H bond of benzylic system, which provides aldehyde and hydrazoic acid (HN3) in situ. This reaction subsequently forms azido alcohol intermediate that transforms into nitrile with the assistance of triflic acid (Br?nsted acid). A range of alcohols and methyl arenes successfully underwent cyanation at room temperature with good to excellent yields and showed good functional group tolerance.

Pd/C-Catalyzed methoxycarbonylation of aryl chlorides

A new protocol for the methoxycarbonylation of aryl chlorides has been developed. Various methyl benzoates were produced in good to excellent yields. Several parameters are crucial for the success of this procedure: 1) the usage of LiOMe as the base or co-nucleophile which facilitate the carbonylative transformation; 2) employing Pd/C as the catalyst to prevent the palladium reduced by MeOH and subsequent agglomerate; 3) CO concentration, excessive CO concentration will directly lead to the termination of the reaction.

Organophotoredox assisted cyanation of bromoarenes: via silyl-radical-mediated bromine abstraction

The insertion of a nitrile (-CN) group into arenes through the direct functionalization of the C(sp2)-Br bond is a challenging reaction. Herein, we report an organophotoredox method for the cyanation of aryl bromides using the organic photoredox catalyst 4CzIPN and tosyl cyanide (TsCN) as the nitrile source. A photogenerated silyl radical, via a single electron transfer (SET) mechanism, was employed to abstract bromine from aryl bromide to provide an aryl radical, which was concomitantly intercepted by TsCN to afford the aromatic nitrile. A range of substrates containing electron-donating and -withdrawing groups was demonstrated to undergo cyanation at room temperature in good yields.

Palladium-Catalyzed, Copper(I)-Promoted Methoxycarbonylation of Arylboronic Acids with O-Methyl S-Aryl Thiocarbonates

Here, we report O-methyl S-aryl thiocarbonates as a versatile esterification reagent for palladium-catalyzed methoxycarbonylation of arylboronic acid in the presence of copper(I) thiophene-2-carboxylate (CuTC). The reaction condition is mild, and a variety of substituents including sensitive-Cl,-Br, and free-NH2 could be tolerated. Further applications in the late-stage esterification of some pharmaceutical drugs demonstrate the broad utility of this method.

Application of Continuous Flow-Flash Chemistry to Scale-up Synthesis of 5-Cyano-2-formylbenzoic Acid

Efficient scale-up synthesis of 5-cyano-2-formylbenzoic acid or its cyclic isomer 6-cyano-3-hydroxy-2-benzofuran-1(3H)-one (1) as a key intermediate for various biologically important compounds has been achieved from isopropyl 2-bromo-5-cyanobenzoate (8c) by means of continuous flow-flash chemistry using flow microreactors. It was found that Br/Li exchange reaction of 8c, bearing both a carboisopropoxy group and a cyano group, with BuLi took place within 0.1 s at -50 °C, and the resulting highly reactive aryllithium intermediate underwent formylation with DMF to afford 1, which is extremely difficult to achieve by a conventional batch process. Optimization of the continuous flow-flash reaction conditions and modification of the reaction system brought about the production of 237 g of 1 from 897 g of 8c in 270 min, without purification by column chromatography. The results suggest that phthalaldehydic acid derivatives bearing electrophilic group(s) can be synthesized conveniently from the corresponding 2-bromobenzoic acid esters by means of flow-flash chemistry using flow microreactors.