20099-53-0

Basic information

• Product Name: 4-(2-OXOACETYL)BENZONITRILE
• Synonyms: 4-(2-OXOACETYL)BENZONITRILE
• CAS NO: 20099-53-0
• Molecular Formula: C₉H₅NO₂
• Molecular Weight: 159.14
• Mol File: 20099-53-0.mol

Chemical Properties

• Boiling Point: 305.114 °C at 760 mmHg
• Flash Point: 138.328 °C
• Appearance: /
• Density: 1.251 g/cm³
• CAS DataBase Reference: 4-(2-OXOACETYL)BENZONITRILE(CAS DataBase Reference)
• NIST Chemistry Reference: 4-(2-OXOACETYL)BENZONITRILE(20099-53-0)
• EPA Substance Registry System: 4-(2-OXOACETYL)BENZONITRILE(20099-53-0)

Safety Data

• Hazardous Substances Data: 20099-53-0(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
4-(2-OXOACETYL)BENZONITRILE is used as a building block for the synthesis of pharmaceuticals due to its reactivity and ability to form complex molecular structures that can target specific biological pathways.
Used in Agrochemical Industry:
4-(2-OXOACETYL)BENZONITRILE is used as a building block for the synthesis of agrochemicals, contributing to the development of effective and targeted pest control agents.
Used in Dye and Pigment Production:
4-(2-OXOACETYL)BENZONITRILE is used as an intermediate in the production of dyes and pigments, enabling the creation of a diverse range of colorants for various applications.
Used in Organic Synthesis:
4-(2-OXOACETYL)BENZONITRILE is used as a reactant in various organic synthesis reactions, allowing for the formation of new compounds with potential applications in different industries.

Upstream product

• 1443-80-7 4-cyanophenyl methyl ketone 
• 20099-89-2 4-Cyanophenacyl bromide 
• 3032-92-6 4-cyanophenylacetylene 

Downstream Products

• 912819-58-0 4-[4-(4-cyano-benzoyl)-1,9b-dihydro-5-oxa-3,3a-diaza-cyclopenta[a]naphthalen-2-yl]-benzyl alcohol 
• 619-65-8 4-cyanobenzoic Acid 
• 912819-59-1 4-[4-(4-cyano-benzoyl)-1,9b-dihydro-5-oxa-3,3a-diaza-cyclopenta[a]naphthalen-2-yl]-benzaldehyde 
• 1048007-25-5 4-(quinoxalin-2-yl)benzonitrile 
• 769944-67-4 1,4-di(t-butoxycarbonyl)-2-(4-cyanophenyl)piperazine 
• 1616777-95-7 4-(2-hydroxy-3-(2-phenyloxazol-5-yl)propanoyl)benzonitrile 
• 446868-17-3 4-[4-hydroxy-5-oxo-6-benzyl-4-hydropyrazin-2-yl]benzenecarbonitrile 

Relevant articles and documents

A novel class for carbonic anhydrases inhibitors and evaluation of their non-zinc binding

In this study, 23 different imidazole derivatives were synthesized, and the inhibitory properties of these derivatives against carbonic anhydrase I and II isoenzymes were investigated for the first time. The inhibition concentrations of the imidazole derivatives were found to be in the range of 2.89–115.5 nM. Docking studies examined the binding properties of the imidazole derivatives, and the structure–activity relationship is discussed. Theoretical calculations showed that the binding mode of the imidazole ring was non-zinc binding.

Catalytic Asymmetric Darzens-Type Epoxidation of Diazoesters: Highly Enantioselective Synthesis of Trisubstituted Epoxides

Highly enantioselective Darzens-type epoxidation of diazoesters with glyoxal derivatives was accomplished using a chiral boron–Lewis acid catalyst, which facilitated asymmetric synthesis of trisubstituted α,β-epoxy esters. In the presence of a chiral oxazaborolidinium ion catalyst, the reaction proceeded in high yield (up to 99 %) with excellent enantio- and diastereoselectivity (up to >99 % ee and >20:1 dr, respectively). The synthetic potential of this method was illustrated by conversion of the products to various compounds such as epoxy γ-butyrolactone, tertiary β-hydroxy ketone and epoxy diester.

Asymmetric Conjugate Addition of α-Cyanoketones to Benzoyl Acrylonitrile Derivatives Using a Diaminomethylenemalononitrile Organocatalyst

A diaminomethylenemalononitrile (DMM) organocatalyst was used to efficiently promote asymmetric conjugate addition of various α-cyanoketones to benzoyl acrylonitrile derivatives. The corresponding 1,5-dicarbonyl compounds containing vicinal tertiary and quaternary stereogenic centers are versatile synthetic intermediates and were obtained in good yields and with excellent enantioselectivities (up to 96% ee). The present study describes the first successful examples of asymmetric conjugate addition reactions of α-cyanoketones with benzoyl acrylonitriles. In addition, the DMM organocatalyst can be recovered and reused up to five times without significant loss of either catalytic activity or enantioselectivity.

Nature of the Nucleophilic Oxygenation Reagent Is Key to Acid-Free Gold-Catalyzed Conversion of Terminal and Internal Alkynes to 1,2-Dicarbonyls

2,3-Dichloropyridine N-oxide, a novel oxygen transfer reagent, allows the conductance of the gold(I)-catalyzed oxidation of alkynes to 1,2-dicarbonyls in the absence of any acid additives and under mild conditions to furnish the target species, including those derivatized by highly acid-sensitive groups. The developed strategy is effective for a wide range of alkyne substrates such as terminal- and internal alkynes, ynamides, alkynyl ethers/thioethers, and even unsubstituted acetylene (40 examples; yields up to 99%). The oxidation was successfully integrated into the trapping of reactive dicarbonyls by one-pot heterocyclization and into the synthesis of six-membered azaheterocycles. This synthetic acid-free route was also successfully applied for the total synthesis of a natural 1,2-diketone.

Modular Synthesis of Di- A nd Trisubstituted Imidazoles from Ketones and Aldehydes: A Route to Kinase Inhibitors

A one-pot and modular approach to the synthesis of 2,4(5)-disubstituted imidazoles was developed based on ketone oxidation, employing catalytic HBr and DMSO, followed by imidazole condensation with aldehydes. This methodology afforded twenty-nine disubstituted NH-imidazoles (23%-85% yield). A three-step synthesis of 20 kinase inhibitors was achieved by employing this oxidation-condensation protocol, followed by bromination and Suzuki coupling in the imidazole ring to yield trisubstituted NH-imidazoles (23%-69%, three steps). This approach was also employed in the synthesis of known inhibitor GSK3037619A.

Oxidative C-C Bond Cleavage for the Synthesis of Aryl Carboxylic Acids from Aryl Alkyl Ketones

A metal-free and one-pot two-step synthesis of aryl carboxylic acids from aryl alkyl ketones has been achieved. The reactions were performed with iodine as the catalyst, DMSO and TBHP as the oxidants. Under the optimal reaction conditions, a number of aryl alkyl ketones could be converted into their corresponding aryl carboxylic acids in good to excellent yields (up to 94%).

Discovery of novel 2-(3-phenylpiperazin-1-yl)-pyrimidin-4-ones as glycogen synthase kinase-3β inhibitors

We herein describe the results of further evolution of glycogen synthase kinase (GSK)-3β inhibitors from our promising compounds containing a 2-phenylmorpholine moiety. Transformation of the morpholine moiety into a piperazine moiety resulted in potent GSK-3β inhibitors. SAR studies focused on the phenyl moiety revealed that a 4-fluoro-2-methoxy group afforded potent inhibitory activity toward GSK-3β. Based on docking studies, new hydrogen bonding between the nitrogen atom of the piperazine moiety and the oxygen atom of the main chain of Gln185 has been indicated, which may contribute to increased activity compared with that of the corresponding phenylmorpholine analogues. Effect of the stereochemistry of the phenylpiperazine moiety is also discussed.

(1, 10B-DIHYDRO-2-(AMINOALKYL- PHENYL)-5H-PYRAZ0L0 [1,5-C] [1,3] BENZ0XAZIN-5-YL) PHENYL METHANONE DERIVATIVES AS HIV VIRAL REPLIATION INHIBITORS

The present invention relates to 5H-pyrazolo[1,5-c][1,3]benzoxazin-5-yl)phenyl methanone derivatives as inhibitors of the viral replication of the HIV virus, processes for their preparation as well as pharmaceutical compositions, their use as medicines, a

(1,10B-DIHYDRO-2-(AMINOCARBONYL-PHENYL)-5H-PYRAZOLO[1,5- C][1,3]BENZOXAZIN-5-YL)PHENYL METHANONE DERIVATIVES AS HIV VIRAL REPLICATION INHIBITORS

The present invention relates to 5H-pyrazolo[1,5-c] [1,3]benzoxazin-5-yl)phenyl methanone derivatives as inhibitors of the viral replication of the HIV virus, processes for their preparation as well as pharmaceutical compositions, their use as medicines,

2, 3, 6-TRISUBSTITUTED-4-PYRIMIDONE DERIVATIVES

A pyrimidone derivative having tau protein kinase 1 inhibitory activity which is represented by formula (I) or a salt thereof, or a solvate thereof or a hydrate thereof; useful for prventive and/or therapeutic treatment of diseass such as neurodegenerative diseases (e.g. Alzheimer disease); wherein Q represents CH or nitrogen atom; R represents a C1-C12 alkyl group; the ring of Formula (I): represents piperazine ring or piperidine ring; each X independently represents a C1-C8 alkyl group, an optionally partially hydrogenated C6-C10 aryl ring, an indan ring or the like; m represents an integer of 1 to 3; each Y independently represents a halogen atom, a hydroxy group, a cyano group, a C1-C6 alkyl group or the like; n represents an integer of 0 to 8; when X and Y or two Y groups are attached on the same carbon atom, they may combine to each other to form a C2-C6 alkylene group.