35276-83-6

Usage

Uses

Used in Pharmaceutical Industry:
2-Methoxybenzoyl acetonitrile is used as a key intermediate for the synthesis of various pharmaceuticals, contributing to the development of new drugs and therapeutic agents. Its role in the production of diverse organic compounds makes it essential for advancing pharmaceutical research and innovation.
Used in Agrochemical Industry:
In the agrochemical sector, 2-Methoxybenzoyl acetonitrile is employed as a precursor in the synthesis of agrochemicals, such as pesticides and herbicides. Its use in this industry aids in the development of more effective and environmentally friendly solutions for agricultural applications.
Used in Specialty Chemicals Industry:
2-Methoxybenzoyl acetonitrile is used as a versatile building block for the preparation of specialty chemicals, which are high-value compounds used in specific applications such as fragrances, dyes, and coatings. Its role in the synthesis of these compounds highlights its importance in creating unique and specialized products.
Used as a Reagent in Organic Synthesis:
2-Methoxybenzoyl acetonitrile is utilized as a reagent in the synthesis of other compounds, including the preparation of heterocyclic compounds. Its ability to participate in various chemical reactions makes it a valuable tool in the field of organic synthesis, facilitating the creation of new and complex molecules.

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

Upstream product

• 75480-74-9 3-Imino-3-(2-methoxy-phenyl)-propionitrile 
• 579-74-8 2-Methoxyacetophenone 
• 143-33-9 sodium cyanide 
• 18293-53-3 2-trimethylsilylacetonitrile 
• 529-28-2 4-iodoanisol 
• 201230-82-2 carbon monoxide 
• 75-05-8 acetonitrile 
• 13939-06-5 molybdenum hexacarbonyl 
• 1121543-12-1 α,α-dibromo-2'-methoxyacetophenone 
• 7335-26-4 ethyl 2-methoxybenzoate 
• 6609-56-9 2-methoxy-benzonitrile 
• 21615-34-9 2-Methoxybenzoyl chloride 
• 31949-21-0 bromomethyl 2-methoxyphenyl ketone 
• 606-45-1 2-methoxybenzoic acid methyl ester 

Downstream Products

• 244233-77-0 1-(2-Nitro-5-chlorophenyl)-3-(2-methoxyphenyl)-5-aminopyrazole 
• 75473-32-4 5-(2-Methoxy-phenyl)-1,3-dihydro-thieno[2,3-e][1,4]diazepin-2-one 
• 75473-50-6 5-(2-Methoxy-phenyl)-1-methyl-1,3-dihydro-thieno[2,3-e][1,4]diazepin-2-one 
• 75473-22-2 2-Iodo-N-[3-(2-methoxy-benzoyl)-thiophen-2-yl]-acetamide 
• 75473-27-7 2-Amino-N-[3-(2-methoxy-benzoyl)-thiophen-2-yl]-acetamide 
• 75473-17-5 2-Chloro-N-[3-(2-methoxy-benzoyl)-thiophen-2-yl]-acetamide 
• 75473-43-7 7-Chloro-5-(2-methoxy-phenyl)-1,3-dihydro-thieno[2,3-e][1,4]diazepin-2-one 
• 1401052-67-2 1-hydroxy-8-methoxyl-3,4-diphenyl-2-naphthonitrile 
• 53882-56-7 Dithiophosphoric acid O-[(E)-2-cyano-1-(2-methoxy-phenyl)-vinyl] ester O'-ethyl ester S-propyl ester 

Relevant academic research and scientific papers

Reaction of 1,3-Bis(het)arylmonothio-1,3-diketones with Sodium Azide: Regioselective Synthesis of 3,5-Bis(het)arylisoxazoles via Intramolecular N-O Bond Formation

An efficient new synthesis of 3,5-bis(het)arylisoxazoles, involving the reaction of 1,3-bis(het)arylmonothio-1,3-diketones with sodium azide in the presence of IBX catalyst, has been reported. The reaction proceeds at room temperature in high yields and is applicable to a broad range of substrates including the synthesis of 5-methyl-3-arylisoxazoles, a key subunit present in several β-lactamase-resistant antibiotics. A probable mechanism for the formation of isoxazoles has been suggested. A few of the 5-styryl/arylbutadienyl-3-(het)arylisoxazoles have also been synthesized by reacting the corresponding 1-(het)aryl-1-(methylthio)-4-(het)arylidene-but-1-en-3-ones with sodium azide at higher temperatures. The reaction of β-ketodithioesters with sodium azide is shown to furnish β-ketonitriles in good yields.

Synthesis and biological evaluation of 7-(aminoalkyl)pyrazolo[1,5-a]pyrimidine derivatives as cathepsin K inhibitors

A series of novel 7-aminoalkyl substituted pyrazolo[1,5-a]pyrimidine derivatives were synthesized and tested for inhibition of cathepsin K. The synthetic methodology comprises cyclization of 5-aminopyrazoles with N-Boc-α-amino acid-derived ynones followed by transformation of the ester and the Boc-amino functions. It allows for easy diversification of the pyrazolo[1,5-a]pyrimidine scaffold at various positions. Molecular docking studies with pyrazolo[1,5-a]pyrimidine derivatives were also performed to elucidate the binding mode in the active site of cathepsin K. The synthesized compounds exhibited moderate inhibition activity (Ki ≥ 77 μM).

One-pot synthesis of benzoylacetonitriles through sequential Pd-catalyzed carbonylation and decarboxylation

Benzoylacetonitrile were prepared through sequential carbonylation and decarboxylation. The palladium-catalyzed carbonylation of aryl iodides and methyl cyanoacetate using Mo(CO)6 as a carbon monoxide source afforded beta-keto cyanoesters, and then the subsequent reaction with Li/H2O produced the desired benzoylacetonitriles.

Pyrazolotriazines as inhibitors of nucleases

The invention provides compounds represented by the structural formula (1): wherein R1, R2, R3 and R4 are as defined in the claims. The compounds are inhibitors of nucleases, and are useful in particular in a method of treatment and/or prevention of proliferative diseases, neurodegenerative diseases, and other genomic instability associated diseases.

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.

Discovery of a novel alpha-7 nicotinic acetylcholine receptor agonist series and characterization of the potent, selective, and orally efficacious agonist 5-(4-acetyl[1,4]diazepan-1-yl)pentanoic acid [5-(4-methoxyphenyl)-1H- pyrazol-3-yl] amide (SEN15924, WAY-361789)

Alpha-7 nicotinic acetylcholine receptors (α7 nAChR) are implicated in the modulation of many cognitive functions such as attention, working memory, and episodic memory. For this reason, α7 nAChR agonists represent promising therapeutic candidates for the treatment of cognitive impairment associated with Alzheimer's disease (AD) and schizophrenia. A medicinal chemistry effort, around our previously reported chemical series, permitted the discovery of a novel class of α7 nAChR agonists with improved selectivity, in particular against the α3 receptor subtype and better ADME profile. The exploration of this series led to the identification of 5-(4-acetyl[1,4] diazepan-1-yl)pentanoic acid [5-(4-methoxyphenyl)-1H-pyrazol-3-yl] amide (25, SEN15924, WAY-361789), a novel, full agonist of the α7 nAChR that was evaluated in vitro and in vivo. Compound 25 proved to be potent and selective, and it demonstrated a fair pharmacokinetic profile accompanied by efficacy in rodent behavioral cognition models (novel object recognition and auditory sensory gating).

Palladium-catalyzed carbonylation with Mo(CO)for the synthesis of benzoylacetonitriles

Benzoylacetonitriles were synthesized by the palladium-catalyzed carbonylation of aryl iodides and trimethylsilylacetonitrile using Mo(CO)as a carbon monoxide source. Pd(PPhCland CuFwere employed as the catalyst and activator, respectively. A variety of aryl iodides bearing alkyl, alkoxy, fluoro, chloro, bromo, nitrile, ester, and ketone groups afforded the corresponding benzoylacetonitriles in moderate to good yields. Georg Thieme Verlag Stuttgart ? New York.

Synthesis of benzoylacetonitriles from Pd-catalyzed carbonylation of aryl iodides and trimethylsilylacetonitrile

Palladium-catalyzed carbonylation of aryl iodides and trimethylsilylacetonitrile to produce benzoylacetonitrile derivatives through a one-pot, three-component reaction is described. This preparation method provides good yields of the carbonylated products without any additional ligands. It has a broad substrate scope with a high tolerance for a variety of functional groups.

Iridium diamine catalyst for the asymmetric transfer hydrogenation of ketones

A simple and very efficient chiral aqua iridium(III) diamine complex leads to excellent enantioselectivities in the asymmetric transfer hydrogenation of various α-cyano and α-nitro ketones. The catalyst provides the ortho-substituted aromatic alcohols with especially high ee values. The diamine ligands can be used directly as chiral ligands; conversion into the corresponding sulfamide is not necessary.

Bromophilic substitution/carbophilic substitution cascade reactions of α,α-dibromo-2-methoxyacetophenone with C-, N- and O-nucleophiles

α,α-Dibromo-2-methoxyacetophenone reacts, under mild reaction conditions, with C-, N- and O-nucleophiles via a bromophilic substitution/protonation/carbophilic substitution cascade process to afford α-monosubstituted-2-methoxyacetophenones in moderate to good yield. The only exception from this reaction pathway is the reaction with the anion derived from malononitrile in which 2-aroyl-1,1,3,3-tetracyanopropene is obtained.