532-54-7

Usage

Uses

Used in Chemical Analysis:
2-Isonitrosoacetophenone is used as a reagent for the detection of ferrous ions, with which it forms a blue color soluble in chloroform. This property makes it a valuable tool in chemical analysis and research, particularly in the identification and quantification of ferrous ions in various samples.
Used in Pharmaceutical Industry:
2-Isonitrosoacetophenone is used to create complexes with copper and amino acids. These complexes have demonstrated enhanced antimicrobial activities, particularly against gram-positive bacteria, and also possess antioxidant properties. This makes them potentially useful in the development of new antimicrobial agents and therapies, as well as in the field of antioxidant research.

Synthesis Reference(s)

The Journal of Organic Chemistry, 39, p. 2558, 1974 DOI: 10.1021/jo00931a022

Purification Methods

Crystallise it from water. [Beilstein 7 IV 2132.]

InChI:InChI=1/C8H7NO2/c10-8(6-9-11)7-4-2-1-3-5-7/h1-6,11H/b9-6-

Upstream product

• 1074-12-0 phenylglyoxal hydrate 
• 94-02-0 ethyl 3-oxo-3-phenylpropionate 
• 624-91-9 methyl nitrite 
• 98-86-2 acetophenone 
• 109-95-5 ethyl nitrite 
• 544-16-1 n-Butyl nitrite 
• 141-52-6 sodium ethanolate 
• 110-46-3 isopentyl nitrite 
• 13735-81-4 1-styrenyloxytrimethylsilane 
• 55984-49-1 N-Methyl-N-nitroso-trans-styrylamin 
• 1075-06-5 2,2-dihydroxy-1-phenyl-ethanone 
• 7647-01-0 hydrogenchloride 
• 60-29-7 diethyl ether 
• 56-23-5 tetrachloromethane 

Downstream Products

• 108488-77-3 1-phenyl-3-piperidino-propane-1,2-dione-2-oxime 
• 114062-10-1 1-(2-diethylamino-ethyl)-3-phenyl-quinoxalinium; chloride-hydrochloride 
• 112223-99-1 1-(2-diethylamino-ethyl)-6-methyl-3-phenyl-quinoxalinium; iodide hydriodide 
• 122764-08-3 1-(2-dibutylamino-ethyl)-3-phenyl-quinoxalinium; chloride-hydrochloride 
• 122765-78-0 1-[2-(2-diethylamino-ethylsulfanyl)-ethyl]-3-phenyl-quinoxalinium; iodide hydriodide 
• 574-16-3 (Z)-benzilmonooxime 
• 613-90-1 benzoyl cyanide 
• 4937-87-5 N-hydroxy-2-oxo-2-phenylethanimidoyl chloride 
• 10349-14-1 4-phenyl-furazan-3-ylamine 
• 5398-63-0 2,5-diphenylpyrazine 
• 1074-12-0 phenylglyoxal hydrate 
• 17016-15-8 anti-phenylglyoxime 
• 26527-40-2 phenylglyoxal-(1Z,2E)-dioxime 
• 90005-59-7 E/Z-mandelaldoxime 

Relevant academic research and scientific papers

Discovery of Hydroxyamidine Derivatives as Highly Potent, Selective Indoleamine-2,3-dioxygenase 1 Inhibitors

In this study, a series of novel hydroxyamidine derivatives were identified as potent and selective IDO1 inhibitors by structure-based drug design. Among them, compounds 13-15 and 18 exhibited favorable enzymatic and cellular activities. Compound 18 showed improved bioavailability in mouse, rat, and dog (F% = 44%, 58.8%, 102.1%, respectively). With reasonable in vivo pharmacokinetic properties, compound 18 was further evaluated in a transgenic MC38 xenograft mouse model. The combination of compound 18 with PD-1 monoclonal antibody showed a synergistic antitumor effect. These data indicated that compound 18 as a potential cancer immunotherapy agent should warrant further investigation.

Site-selective conversion of azido groups at carbonyl α-positions into oxime groups leading triazide to a triple click conjugation scaffold

This paper reports the selective conversion of alkyl azido groups at the carbonyl α-position into oximes through β-elimination of dinitrogen, followed by transoximation. With this method and diazo conversion, a triazido molecule was transformed into a triple click conjugation scaffold allowing one-pot four-component coupling.

Arylglyoxal oximes as putative C-nucleophiles in eliminative nucleophilic substitution process

Reaction of arylglyoxal oximes ArCOCH=NOH (Ar = 4-MeOC6H4, Ph) with 5-arylfurazanopyrazines proceeds as vicarious nucleophilic substitution of hydrogen in pyrazine ring with the elimination of hyponitrous acid, affording 5-(aroylmethylidene)-6-aryl-4H-furazano[3,4-b]pyrazines. Structure of the product was confirmed by X-ray diffraction.

The synthesis and characterization of (MSalen/salophen/saldeta/salpy) [M=Fe(III) or Cr(III)] capped heteromultinuclear schiff bases-dioxime Ni(II) complexes: Their thermal and magnetic behaviours

Chlorophenylglyoxime and Ligand Complexes ([M(Salen/Salophen)]2O, [M(Saldeta/Salpy)Cl] shortened as LC, M = Fe(III) or Cr(III)) have been synthesized. 3,5-dicarboxyanilinophenylglyoxime (5) and 4-carboxyphenylhydrazinophenylglyoxime (6) have been synthesized with the reaction of chlorophenylglyoxime and 5-aminoisophtalalic acid or 4-hydrazinobenzoic acid. [M(Salen/Salophen/Saldeta/Salpy)-3,5-dicarboxyanilinophenyl-glyoxime)] (7–14) or [M(Salen/Salophen)-4-carboxyphenylhydrazinophenylglyoxime)] (15–22) have been synthesized from (5) or (6) and LCs. The new heterotrinuclear and pentanuclear complexes (23–38) have been obtained from (7–22) and Ni(II) salt. Then, heteronuclear and BF2 + capped vic-dioxime complexes (39–54) have been synthesized. The complexes have been characterized as low-spin (S = 1/2) distorted octahedral [FeIII(Salen/Salophen)], high-spin (S = 5/2) distorted octahedral [FeIII(Saldeta/Salpy)] and (S = 3/2) distorted octahedral [CrIII(Salen/Salophen/Saldeta/Salpy)] bridged by COO? groups. The structure of all ligand and complexes were identified by using elemental analysis, thermal analyses, magnetic susceptibility, LC-MS, ICP-AES, 1H-NMR and FT-IR spectral data.

Hydroheteroarylation of Unactivated Alkenes Using N-Methoxyheteroarenium Salts

We report the first reductive coupling of unactivated alkenes with N-methoxy pyridazinium, imidazolium, quinolinium, and isoquinolinium salts under hydrogen atom transfer (HAT) conditions, and an expanded scope for the coupling of alkenes with N-methoxy pyridinium salts. N-Methoxy pyridazinium, imidazolium, quinolinium, and isoquinolinium salts are accessible in 1-2 steps from the commercial arenes or arene N-oxides (25-99%). N-Methoxy imidazolium salts are accessible in three steps from commercial amines (50-85%). In total 36 discrete methoxyheteroarenium salts bearing electron-donating, electron-withdrawing, alkyl, aryl, halogen, and haloalkyl substituents were prepared (several in multigram quantities) and coupled with 38 different alkenes. The transformations proceed under neutral conditions at ambient temperature, provide monoalkylation products exclusively, and form a single alkene addition regioisomer. Preparatively useful and complementary site selectivities in the addition of secondary and tertiary radicals to pyidinium salts are documented: harder secondary radicals favor C-2 addition (2->10:1), while softer tertiary radicals favor bond formation to C-4 (4.7->29:1). A diene possessing a 1,2-disubstituted and 2,2-disubstituted alkene undergoes hydropyridylation at the latter exclusively (61%) suggesting useful site selectivities can be obtained in polyene substrates. The methoxypyridinium salts can also be employed in dehydrogenative arylation, borono-Minisci, and tandem arylation processes. Mechanistic studies support the involvement of a radical process.

Single-Step Modular Synthesis of Unsaturated Morpholine N-Oxides and Their Cycloaddition Reactions

A single-flask procedure for the generation of α-keto-N-alkenylnitrones through a Chan–Lam coupling and subsequent spontaneous 6π electrocyclization of these intermediates for the synthesis of 2H-1,4-oxazine N-oxides has been developed for a variety of α-ketooximes and alkenylboronic acids. This transformation provides a new approach to C-substituted unsaturated morpholine derivatives that are poised to undergo further functionalization for the preparation of a diverse array of novel heterocyclic structures. The scope of the new method for the synthesis of 2H-1,4-oxazine N-oxides is discussed, in addition to initial studies describing the cycloaddition reactivity of these new heterocyclic intermediates.

Water-Assisted Nitrile Oxide Cycloadditions: Synthesis of Isoxazoles and Stereoselective Syntheses of Isoxazolines and 1,2,4-Oxadiazoles

Conventional methods generate nitrile oxides from oxime halides in organic solvents under basic conditions. However, the present work revealed that water-assisted generation of nitrile oxides proceeds under mild acidic conditions (pH 4-5). Cycloadditions of nitrile oxides with alkynes and alkenes easily occurred in water without using catalysts, thus yielding isoxazoles and isoxazolines, respectively, with excellent stereoselectivity toward five- and six-membered cyclic alkenes. A double stereoselective cycloaddition of two units of a nitrile oxide with cyclohexene was also achieved, thus yielding 1,2,4-oxadiazole derivatives having a unique hybrid isoxazoline-oxadiazole skeleton. Enantiomerically pure isoxazolines were prepared from monoterpenes with a ring strain. In one case, the isoxazoline with a butterfly-like structure was simply prepared, and it might be used as a ligand in asymmetric catalysis.

Regioselective Synthesis of V-Shaped Bistriazinyl-phenanthrolines

A new, regioselective synthesis of V-shaped 2,9-bis(6-(4-halophenyl)-1,2,4-triazin-3-yl)-1,10-phenanthrolines (4XPhBTPhen) ligands was developed, creating access to a simple and reliable synthesis of precursors for future supramolecular actinide complexing systems. Described is a reactant-directed regioselective synthetic method, which was found to be high yielding and reliable and yields exclusively 6,6′-phenyl BTPhen derivatives (including 4-chloro and 4-bromo) in five simple steps. Molecular and crystal structures of PhBTP and PhBTPhen products are fully determined and both were found to be in space group C2/c. Additionally, molecular and crystal structures of Z and E isomers of 2-hydrazono-2-phenylacetaldehyde oxime, a reagent in the synthetic route, reveal existence of strong intramolecular N-H?O hydrogen bonding in the Z isomer explaining its lower solubility in water.

Copper-catalyzed direct amination of 1,2,3-triazole N-oxides by C-H activation and C-N coupling

An efficient approach for the synthesis of 4-amino-2-aryl- 1,2,3-triazole derivatives has been developed through the copper-catalyzed direct C-H amination of 2-aryl-1,2,3-triazole N-oxides under mild reaction conditions. Various amines, including primary and secondary aliphatic and aromatic amines, can be employed as effective coupling partners. The general performance of our method was also demonstrated by the oxidative amination of thiazole and imidazole N-oxides.

Green and highly selective protocol for the synthesis of oximes

A green and efficient protocol has been developed for the synthesis of either exclusively a monoxime or exclusively a dioxime from a host of 1,2-dicarbonyl compounds on silica.