21667-60-7

Usage

Uses

Used in Pharmaceutical Industry:
3-Methoxybenzoylacetonitrile is used as a key intermediate in the synthesis of various pharmaceuticals for its ability to contribute to the formation of complex organic molecules that are integral to the development of new drugs.
Used in Organic Synthesis:
In the field of organic chemistry, 3-Methoxybenzoylacetonitrile serves as a versatile building block for the creation of a wide range of organic compounds, leveraging its unique structure to facilitate various chemical reactions and syntheses.

InChI:InChI=1/C10H9NO2/c1-13-9-4-2-3-8(7-9)10(12)5-6-11/h2-4,7H,5H2,1H3

Upstream product

• 5368-81-0 methyl 3-methoxybenzoate 
• 75-05-8 acetonitrile 
• 143-33-9 sodium cyanide 
• 5000-65-7 2-bromo-3'-methoxyacetophenone 
• 18293-53-3 2-trimethylsilylacetonitrile 
• 766-85-8 3-methoxy-1-iodobenzene 
• 201230-82-2 carbon monoxide 
• 474843-37-3 3-chloro-3-(3-methoxyphenyl)prop-2-enenitrile 
• 75073-56-2 1-formyl-2-chloro-2-(m-methoxyphenyl)ethylene 
• 773837-37-9 sodium cyanide 
• 2398-37-0 3-methoxyphenyl bromide 
• 1116-98-9 cyanoacetic acid tert-butyl ester 
• 82102-37-2 9-methyl-9H-fluorene-9-carbonyl chloride 
• 586-38-9 3-Methoxybenzoic acid 

Downstream Products

• 103205-23-8 3-hjydroxy-3-(3-methoxyphenyl)propanenitrile 
• 255841-10-2 (S)-3-hydroxy-3-(3'-methoxyphenyl)propanenitrile 
• 836684-71-0 4-(N-phenyl)amino-3-(3-methoxyphenyl)carbonylacrylonitrile 
• 1401051-71-5 4-methoxyl-2,3,7,8-tetraphenylnaphtho[1,8-bc]pyran-9-carbonitrile 
• 1401051-78-2 6-methoxyl-2,3,7,8-tetraphenylnaphtho[1,8-bc]pyran-9-carbonitrile 
• 501379-83-5 2-(3-methoxybenzoyl)-4-oxo-4-pyridin-3-yl-butyronitrile 
• 740035-73-8 2-Amino-2-(3-methoxy-benzoyl)-acetonitril 
• 249937-47-1 5-amino-1-(4-fluorophenyl) 4-{3-[(2,2-dimethyl-1,3-dioxolan-5(S)-yl)methoxy]benzoyl}pyrazole 
• 1044590-54-6 [5-amino-1-(4-fluorophenyl)-1H-pyrazol-4-yl]{3-[(R)-(2,2-dimethyl-1,3-dioxolan-4-yl)methoxy]phenyl}ketone 
• 249936-55-8 [14C]-Ro 3201195 
• 249937-22-2 [5-amino-1-(4-fluorophenyl)-1H-pyrazol-4-yl]-[3-(2-bromoethoxy)phenyl]methanone 
• 249937-13-1 [5-amino-1-(4-fluorophenyl)-1H-pyrazol-4-yl]-(3-hydroxyphenyl)methanone 
• 249937-12-0 [5-amino-1-(4-fluorophenyl)-1H-pyrazol-4-yl]-(3-methoxyphenyl)methanone 

Relevant academic research and scientific papers

One-Pot Four-Component Coupling Approach to Polyheterocycles: 6 H-Furo[3,2- f]pyrrolo[1,2- d][1,4]diazepine

A novel polyheterocyclic chemical space, 6H-furo[3,2-f]pyrrolo[1,2-d][1,4]diazepine, was generated by a one-pot four-component coupling reaction where multiple bonds (three C-C, one C-O, and one C-N) were formed through a domino sequence. Two heterocyclic rings (furan and diazepine) were sequentially constructed from the monocyclic pyrrole derivative under environment-friendly reaction conditions to furnish the tricyclic fused scaffold.

Deadly KCN and pricey metal free track for accessing β-ketonitriles employing mild reaction conditions

A one pot synthesis of β-ketonitriles from readily accessible 3-chloropropenals using economically benign iodine, aqueous ammonia and sodium hydroxide solution, employing mild reaction conditions have been described. This report presents a convenient, inexpensive, highly toxic-matter-free and eco-friendly approach for β-ketonitriles.

Synthesis of α-Ketoamides from β-Ketonitriles and Primary Amines: A Catalyst-Free Oxidative Decyanation–Amidation Reaction

AN oxidative decyanation–amidation of β-ketonitriles and primary amines readily occurs using hydrogen peroxide sodium carbonate adduct (Na2CO3·1.5H2O2), K2CO3, and 1,4-dioxane. This reactio

Development of inhibitors against mycobacterium abscessus tRNA (m1G37) Methyltransferase (TrmD) Using Fragment-Based Approaches

Mycobacterium abscessus (Mab) is a rapidly growing species of multidrug-resistant nontuberculous mycobacteria that has emerged as a growing threat to individuals with cystic fibrosis and other pre-existing chronic lung diseases. Mab pulmonary infections are difficult, or sometimes impossible, to treat and result in accelerated lung function decline and premature death. There is therefore an urgent need to develop novel antibiotics with improved efficacy. tRNA (m1G37) methyltransferase (TrmD) is a promising target for novel antibiotics. It is essential in Mab and other mycobacteria, improving reading frame maintenance on the ribosome to prevent frameshift errors. In this work, a fragment-based approach was employed with the merging of two fragments bound to the active site, followed by structure-guided elaboration to design potent nanomolar inhibitors against Mab TrmD. Several of these compounds exhibit promising activity against mycobacterial species, including Mycobacterium tuberculosis and Mycobacterium leprae in addition to Mab, supporting the use of TrmD as a target for the development of antimycobacterial compounds.

KINASE MODULATORS FOR THE TREATMENT OF CANCER

A method of treating cancer in which a compound that inhibits the expression, production or release of IL-10 by immune cells is combined with a compound that stimulates the production of IL-12 when given in combination with, or in the presence of TNFa. Sa

Palladium-Catalyzed Carbonylative α-Arylation of tert -Butyl Cyanoacetate with (Hetero)aryl Bromides

A three-component coupling protocol has been developed for the generation of 3-oxo-3-(hetero)arylpropanenitriles via a carbonylative palladium-catalyzed α-arylation of tert-butyl 2-cyanoacetates with (hetero)aryl bromides followed by an acid-mediated decarboxylation step. Through the combination of only a stoichiometric loading of carbon monoxide and mild basic reaction conditions such as MgCl2 and dicyclohexylmethylamine for the deprotonation step, an excellent functional group tolerance was ensured for the methodology. Through the use of 13C-labeled carbon monoxide generated from 13COgen, the corresponding 13C-isotopically labeled β-ketonitriles were obtained, and these products could subsequently be converted into cyanoalkynes and 3-cyanobenzofurans with site specific 13C-isotope labeling. (Chemical Equation Presented).

The effect of RO3201195 and a pyrazolyl ketone P38 MAPK inhibitor library on the proliferation of Werner syndrome cells

Microwave-assisted synthesis of the pyrazolyl ketone p38 MAPK inhibitor RO3201195 in 7 steps and 15% overall yield, and the comparison of its effect upon the proliferation of Werner Syndrome cells with a library of pyrazolyl ketones, strengthens the evidence that p38 MAPK inhibition plays a critical role in modulating premature cellular senescence in this progeroid syndrome and the reversal of accelerated ageing observed in vitro on treatment with SB203580.

Divergent Reactivity in the Reaction of β-Oxodithioesters and Hydroxylamine: Access to β-Ketonitriles and Isoxazoles

Starting from β-oxodithioesters and hydroxylamine, two completely different transformations afford either β-ketonitriles or isoxazoles with high chemoselectivity depending on the reaction conditions. The reaction of β-oxodithioesters with hydroxylamine in EtOH at room temperature in daylight gave β-ketonitriles in high yields. On the other hand, 3-methylthio-isoxazoles were efficiently obtained as the final products by heating the mixture of β-oxodithioesters and hydroxylamine in HOAc at 90 °C.

Chemo- And stereoselective reduction of β-keto-α-oximino nitriles by using baker's yeast

The baker's yeast mediated reduction of β-keto-α-oximino nitriles 3 at 20 ° C gave β-hydroxy-α-oximino nitriles 4 in high yields with high enantiomeric purity [enantiomeric excess (ee) values >99%]. At room temperature, the same reaction afforded the product in a slightly lower yield. The β-hydroxy-α-oximino nitriles 4 were obtained as single stereoisomers according to chiral GC-MS analyses and the 1H and 19F NMR spectra of the corresponding Mosher esters. The abso-lute stereochemistry of alcohol 4a was determined by hydrolysis of its oximino nitrile group followed by conversion into its corresponding α-hydroxy ester. The β-hydroxy-α-oximino nitrile products were further submitted to oxime- and nitrileselective transformations. This chemo- and stereoselective reduction can be used to generate important chiral building blocks.

Cascade synthesis of 3-aza-bicyclo[3.1.0]hex-2-ene derivatives from N-allyl enamines

An efficient iodine-mediated cascade synthesis of 3-aza-bicyclo[3.1.0]hex-2-ene derivatives from easily prepared N-allyl enamines has been developed. The advantages of the reaction include facilitative preparation of substrates 3a-t, good functional group tolerance and transition-metal-free conditions.