614-21-1

Usage

Uses

Used in Chemical Research:
Benzoylnitromethane is used as a research compound for studying the kinetics of proton transfer to various bases. This helps in understanding the fundamental chemical reactions and interactions that occur in different chemical systems.
Used in Pharmaceutical Industry:
Benzoylnitromethane is used as an intermediate in the synthesis of pharmaceutical compounds. Its unique chemical properties make it a valuable component in the development of new drugs and medications.
Used in Organic Synthesis:
Benzoylnitromethane is used as a reagent in organic synthesis, particularly in the preparation of various organic compounds. Its ability to transfer protons makes it a useful tool in the synthesis of complex organic molecules.
Used in Analytical Chemistry:
Benzoylnitromethane is used as an analytical reagent in various analytical techniques, such as spectrophotometry and chromatography. Its unique properties allow for the accurate determination of different chemical compounds and their concentrations.

InChI:InChI=1/C8H7NO3/c10-8(6-9(11)12)7-4-2-1-3-5-7/h1-5H,6H2

Upstream product

• 613-90-1 benzoyl cyanide 
• 75-52-5 nitromethane 
• 4636-16-2 iodoacetophenone 
• 532-54-7 oxo-phenyl-acetaldehyde oxime 
• 141377-54-0 2-nitro-1-phenylethan-1-ol 
• 98-86-2 acetophenone 
• 134-81-6 benzil 
• 1795-99-9 3-morpholin-4-yl-2-nitro-3-phenyl-acrylic acid ethyl ester 
• 93-58-3 benzoic acid methyl ester 
• 3277-27-8 diethyl benzoylphosphonate 
• 98-81-7 1-bromovinylbenzene 
• 2206-94-2 1-acetoxy-1-phenylethene 
• 1796-00-5 4-(2-nitro-1-phenyl-vinyl)-morpholine 
• 4714-45-8 α-Dimethylamino-benzyliden-nitromethan 

Downstream Products

• 100620-83-5 3-[2]furyl-2,4-dinitro-1-phenyl-butan-1-one 
• 100620-80-2 2,4-dinitro-1-phenyl-3-[2]thienyl-butan-1-one 
• 100518-37-4 2,6-diamino-5-(2-nitro-1-phenyl-ethylLiDenamino)-3H-pyrimidin-4-one 
• 5443-79-8 3-nitro-2-phenylquinoline 
• 25187-18-2 6-methyl-2-phenylquinoxalin 
• 57433-51-9 7-methyl-2-phenyl-quinoxaline 
• 64935-22-4 (2-nitro-1-phenyl-ethyliden)-aniline 
• 4937-87-5 N-hydroxy-2-oxo-2-phenylethanimidoyl chloride 
• 5021-43-2 2-phenylquinoxaline 
• 64935-31-5 2-nitro-1-phenyl-ethanone-phenylhydrazone 
• 18315-79-2 E-β-benzoyl-β-nitrostyrene 
• 96039-99-5 3-hydroxy-2-nitro-1-phenyl-propan-1-one 
• 101351-40-0 2,4-dinitro-1,3-diphenyl-butan-1-one 
• 14450-97-6 2-phenyl-glyoxylohydroximoyl bromide 

Relevant academic research and scientific papers

Nickel-Catalyzed Reductive Cross-Coupling of N-Acyl and N-Sulfonyl Benzotriazoles with Diverse Nitro Compounds: Rapid Access to Amides and Sulfonamides

Herein we report a Ni-catalyzed reductive transamidation of conveniently available N-acyl benzotriazoles with alkyl, alkenyl, and aryl nitro compounds, which afforded various amides with good yields and a broad substrate scope. The same catalytic reaction conditions were also applicable for N-sulfonyl benzotriazoles, which could undergo smooth reductive coupling with nitroarenes and nitroalkanes to afford the corresponding sulfonamides.

Efficient Synthesis of α-Ketothioamides From α-Nitroketones, Amines or DMF and Elemental Sulfur Under Oxidant-Free Conditions

We have developed a practical, general protocol for denitration of readily available α-nitroketones with sulfur and amines to access a broad range of α-ketothioamides under mild conditions. Such a reaction proceeds under metal-, oxidant-, and catalyst-free conditions to provide synthetically useful α-ketothioamides. Furthermore, the mild reaction conditions tolerate a wide range of substrates especially for the synthesis of aliphatic α-ketothioamides which are rarely reported.

Synthesis of 3-nitroindoles by sequential paired electrolysis

3-Nitroindoles are synthetically versatile intermediates but current methods for the preparation hinder their widespread application. Herein, we report that nitroenamines undergo electrochemical cyclisation to 3-nitroindoles in the presence of potassium iodide. Detailed control experiments and cyclic voltammogram studies infer the reaction proceedsviaa sequential paired electrolysis process, beginning with anodic oxidation of iodide (I?) to the iodine radical (I˙), which facilitates cyclisation of the nitroenamine to give a 3-nitroindolinyl radical. Cathodic reduction and protonation generates a 3-nitroindoline that upon oxidation forms the 3-nitroindole.

One-pot synthesis of 5-phenylsulfonyl-3-aroylisoxazolines and 3-aroylisoxazoles from alkynes and (phenylsulfonyl)ethene

Iron(III) nitrate-assisted cycloaddition of (phenylsulfonyl)ethene to arylacetylenes in the presence of KI affords 5-phenylsulfonyl-3-aroylisoxazolines whose treatment with K2CO3 provides 4,5-unsubstituted 3-aroylisoxazoles. Both synthetic steps can be performed in a one-pot manner.

Iron Nitrate-Mediated Selective Synthesis of 3-Acyl-1,2,4-oxadiazoles from Alkynes and Nitriles: The Dual Roles of Iron Nitrate

A direct strategy for the selective synthesis of 3-acyl-1,2,4-oxadiazoles from alkynes and nitriles has been developed under iron(III) nitrate-mediated conditions. The mechanism includes three sequential procedures: Iron(III) nitrate-mediated nitration of

Denitrative imino-diaza-Nazarov cyclization: Synthesis of pyrazoles

An iodine-catalyzed denitrative imino-diaza-Nazarov cyclization (DIDAN) methodology has been developed for the synthesis of pyrazoles with high to excellent yields by using α-nitroacetophenone derivatives and in situ generated hydrazones. The key transformation of this oxidative 4π-electrocyclization proceeds through an enamine-iminium ion intermediate. This rapid one-pot DIDAN protocol results in the selective generation of C-C and C-N bonds and cleavage of a C-N bond. This journal is

Sustainable Palladium-Catalyzed Tsuji-Trost Reactions Enabled by Aqueous Micellar Catalysis

Palladium-catalyzed allylic substitution, or "Tsuji-Trost"reactions, can be run under micellar catalysis conditions featuring not only chemistry in water but also numerous combinations of reaction partners that require low levels of palladium, typically on the order of 1000 ppm (0.1 mol %). These couplings are further characterized by especially mild conditions, leading to a number of cases not previously reported in an aqueous micellar medium. Inclusion of diverse nucleophiles, such as N-H heterocycles, alcohols, dicarbonyl compounds, and sulfonamides is described. Intramolecular cyclizations further illustrate the broad utility of this process. In addition to recycling studies, a multigram scale example is reported, indicative of the prospects for scale up.

Ionic-Liquid Controlled Nitration of Double Bond: Highly Selective Synthesis of Nitrostyrenes and Benzonitriles

Unprecedented in literature, the conversion of aryl alkenes into β-nitrostyrenes (2) or benzonitriles (3) with sodium nitrite can be governed by an appropriate choice of ionic liquid (IL) medium. A general trend was found for the selectivity of these processes, which depends on the nature of IL, with imidazolium-based ILs, such as [Bmim]Cl, that favor the C–H nitration leading to β-nitrostyrenes, while tetraalkylammonium-based ILs, such as TBAA, privilege the C=C bond cleavage affording benzonitriles. Besides a substrate scope, mechanistic hypotheses were provided on the origin of the different selectivity in the two kinds of ILs, based on their own tunable properties such as polarity, viscosity, and solvent cage effects.

Imidazolium-Based Ionic Network as a Robust Heterogeneous Catalyst in Synthesis of Phenacyl Derivatives

A new imidazolium-based poly(ionic liquid) has been synthesized and used as a robust heterogeneous catalyst for the preparation of phenacyl derivatives by an SN2 reaction of different phenacyl bromides with a broad range of nucleophiles. The products are obtained in high yields under mild conditions. The catalyst can be recycled efficiently.

Diacylfuroxans Are Masked Nitrile Oxides That Inhibit GPX4 Covalently

GPX4 represents a promising yet difficult-to-drug therapeutic target for the treatment of, among others, drug-resistant cancers. Although most GPX4 inhibitors rely on a chloroacetamide moiety to modify covalently the protein's catalytic selenocysteine residue, the discovery and mechanistic elucidation of structurally diverse GPX4-inhibiting molecules have uncovered novel electrophilic warheads that bind and inhibit GPX4. Here, we report our discovery that diacylfuroxans can act as masked nitrile oxide prodrugs that inhibit GPX4 covalently with unique cellular and biochemical reactivity compared to existing classes of GPX4 inhibitors. These observations illuminate a novel molecular mechanism of action for biologically active furoxans and also expand the collection of reactive groups capable of targeting GPX4.