53882-80-7

Usage

Uses

Used in Pharmaceutical Industry:
2-Bromobenzoylacetonitrile is used as a synthetic intermediate for the production of various pharmaceuticals, leveraging its reactivity to facilitate the creation of diverse medicinal compounds. Its role in drug synthesis is crucial for developing new treatments and enhancing existing ones.
Used in Agrochemical Industry:
In the agrochemical sector, 2-Bromobenzoylacetonitrile is employed as a precursor in the synthesis of pesticides and other agrochemical products. Its chemical properties allow for the development of effective compounds aimed at protecting crops and improving agricultural yields.
Used in Organic Chemistry Research:
2-Bromobenzoylacetonitrile serves as a valuable research tool in organic chemistry, used to explore novel chemical reactions and mechanisms. Its ability to undergo a wide range of transformations makes it instrumental in advancing the understanding of organic reactions and the creation of new chemical entities.
Used in the Production of Functionalized Compounds:
2-Bromobenzoylacetonitrile is utilized as a starting material for the synthesis of various functionalized compounds, which can be further modified for specific applications in different industries. Its versatility ensures its place as a key component in the development of new materials and chemical products.

InChI:InChI=1/C9H6BrNO/c10-8-4-2-1-3-7(8)9(12)5-6-11/h1-4H,5H2

Upstream product

• 610-94-6 2-bromobenzoic acid methyl ester 
• 75-05-8 acetonitrile 
• 1429790-16-8 methyl 3-(2-bromophenyl)-3-oxopropanedithioate 
• 88562-26-9 2-bromobenzoyl cyanide 
• 590-17-0 cyanomethyl bromide 
• 6091-64-1 2-bromobenzoic acid ethyl ester 

Downstream Products

• 295788-81-7 2-bromobenzoyldideuterioacetonitrile 
• 1312605-99-4 (2-(2-(methylsulfonyl)phenyl)-1,5-naphthyridin-3-yl)methanol 
• 1312605-92-7 (7-fluoro-2-(2-(methylsulfonyl)phenyl)-1,5-naphthyridin-3-yl)methanol 
• 1312606-04-4 4-Amino-6-((1-(2-(2-(methylsulfonyl)phenyl)-1,5-naphthyridin-3-yl)ethyl)amino)-5-pyrimidinecarbonitrile 
• 1312606-03-3 1-(2-(2-(methylsulfonyl)phenyl)-1,5-naphthyridin-3-yl)ethanamine 
• 1312606-02-2 2-(1-(2-(2-(methylsulfonyl)phenyl)-1,5-naphthyridin-3-yl)ethyl)isoindoline-1,3-dione 
• 1312606-00-0 2-(2-(methylsulfonyl)phenyl)-1,5-naphthyridine-3-carbaldehyde 
• 1312606-01-1 methyl (2-(2-(methylsulfonyl)phenyl)-1,5-naphthyridin-3-yl)methanol 
• 1312605-98-3 methyl 2-(2-(methylsulfonyl)phenyl)-1,5-naphthyridine-3-carboxylate 
• 1312605-59-6 4-amino-6-(((1R)-1-(2-(2-(methylsulfonyl)phenyl)-1,5-naphthyridin-3-yl)ethyl)amino)-5-pyrimidinecarbonitrile 
• 1312605-58-5 4-amino-6-(((1S)-1-(2-(2-(methylsulfonyl)phenyl)-1,5-naphthyridin-3-yl)ethyl)amino)-5-pyrimidinecarbonitrile 
• 1312605-97-2 4-amino-6-((1-(7-fluoro-2-(2-(methylsulfonyl)phenyl)-1,5-naphthyridin-3-yl)ethyl)amino)-5-pyrimidinecarbonitrile 
• 1312605-96-1 1-(7-fluoro-2-(2-(methylsulfonyl)phenyl)-1,5-naphthyridin-3-yl)ethanamine 
• 1312605-95-0 2-(1-(7-Fluoro-2-(2-(methylsulfonyl)phenyl)-1,5-naphthyridin-3-yl)ethyl)isoindoline-1,3-dione 

Relevant academic research and scientific papers

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.

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.

Design, synthesis, and evaluation of 2-aryl-7-(3′,4′-dialkoxyphenyl)-pyrazolo[1,5-a]pyrimidines as novel PDE-4 inhibitors

Described herein is design, synthesis, and biological evaluation of novel series of 2-aryl-7-(3′,4′-dialkoxyphenyl)-pyrazolo[1,5-a]pyrimidines acting as inhibitors of type 4 phosphodiesterase (PDE4) which is known as a good target for the treatment of asthma and COPD. For this purpose, structure optimization was conducted with the aid of structure-based drug design using the known X-ray crystallography. Also, biological effects of these compounds on the target enzyme were evaluated by using in vitro assays, leading to the potent and selective PDE-4 inhibitor (IC50 10 nM).

Indium-mediated coupling of bromoacetonitriles with aromatic acyl cyanides: convenient synthesis of aromatic α-cyano ketones

Indium-mediated coupling of bromoacetonitrile and 2-bromopropionitrile with a variety of aromatic acyl cyanides afforded the corresponding aromatic α-cyano ketones in moderate to good yields under mild and neutral conditions.

Enolate Ions as ss-Activators of ortho-metalation: Direct Synthesis of 3-Aminoindenones

ss-Ketonitriles derived from a Claisen condensation of benzoate esters with alkyl- or phenylacetonitriles lead to 3-aminoindenones in the presence of excess LDA. This new reaction is also applicable to pyridine carboxylic esters. All of the 3-aminoindenones and their aza analogues can be hydrolyzed by acid to give the corresponding 1,3-indandiones. The mechanism of the reaction falls into the directed-ortho-metalation class in which the initial enolate ion of the keto-nitrile directs self-metalation at an ortho position. The new anion then cyclizes onto the nitrile group to generate an aminoindenone. Surprisingly the simplest member of the series, benzoylacetonitrile, does not undergo cyclization. Mechanistic isotope studies revealed that this substance preferentially and directly forms a dianion on the side chain, which is not further deprotonated at the ortho position of the aromatic ring.