2912-98-3

Usage

Uses

Used in Organic Synthesis:
N-(1-Pyridin-4-yl-ethyl)-hydroxylamine is used as a reagent for the conversion of carbonyl compounds to oximes, facilitating important transformations in organic chemistry.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, N-(1-Pyridin-4-yl-ethyl)-hydroxylamine serves as a key intermediate in the synthesis of various drugs, contributing to the development of new medicinal compounds.
Used in Materials Science:
N-(1-Pyridin-4-yl-ethyl)-hydroxylamine is utilized in the field of materials science as a component in the fabrication of nanostructures and functional materials, broadening its applications beyond traditional chemical reactions.

InChI:InChI=1/C8H11NO/c1-7(9-10)8-5-3-2-4-6-8/h2-7,9-10H,1H3

Upstream product

• 613-91-2 acetophenone oxime 
• 127104-39-6 N-α-methyl benzyl-O-benzoyl hydroxylamine hydrochloride 
• 16528-57-7 tin(II) benzenethiolate 
• 7214-61-1 (1-nitroethyl)benzene 
• 136386-26-0 C₇H₁₃NO₂ 
• 71-43-2 benzene 
• 50314-86-8 acetophenone oxime 
• 98-86-2 acetophenone 
• 6097-58-1 ethyl 2-phenyl-2-aminoacetate 
• 2835-06-5 phenylglycin 
• 100-42-5 styrene 
• 1361044-66-7 [¹⁸O]-acetophenone oxime 
• 10341-75-0 (E)-1-phenylethanone oxime 
• 3886-69-9 (R)-1-phenyl-ethyl-amine 

Downstream Products

• 136386-29-3 N-(1-phenylethyl)-N-hydroxyurea 
• 127104-27-2 N-ethylidene-1-phenylethanamine N-oxide 
• 127180-97-6 (+/-)-N-(2-methylpropylidene)-1-phenylethanamine N-oxide 
• 172101-72-3 N-(α-methylbenzyl)-N-hydroxysuccinamic acid 
• 476686-97-2 N-(1-phenylethyl)-O-thiopivaloylhydroxylamine 
• 21003-57-6 (R,S)-bis(1-phenylethyl)amine 
• 10024-74-5 (R*,R*)-N-(1'-phenylethyl)-1-phenylethylamine 
• 127180-95-4 (R*,S*)-N-hydroxy-N-(1-phenylethyl)-1-phenylethanamine 
• 126927-41-1 (R*,R*)-N-hydroxy-N-(1-phenylethyl)-1-phenylethanamine 
• 127104-52-3 (R*,S*)-diethyl N,N-bis(1-phenylethyl)amino phosphate 
• 127104-51-2 (R*,R*)-diethyl N,N-bis(1-phenylethyl)amino phosphate 

Relevant academic research and scientific papers

Analogues of the Herbicide, N-Hydroxy- N-isopropyloxamate, Inhibit Mycobacterium tuberculosis Ketol-Acid Reductoisomerase and Their Prodrugs Are Promising Anti-TB Drug Leads

New drugs to treat tuberculosis (TB) are urgently needed to combat the increase in resistance observed among the current first-line and second-line treatments. Here, we propose ketol-acid reductoisomerase (KARI) as a target for anti-TB drug discovery. Twenty-two analogues of IpOHA, an inhibitor of plant KARI, were evaluated as antimycobacterial agents. The strongest inhibitor of Mycobacterium tuberculosis (Mt) KARI has a Ki value of 19.7 nM, fivefold more potent than IpOHA (Ki = 97.7 nM). This and four other potent analogues are slow- and tight-binding inhibitors of MtKARI. Three compounds were cocrystallized with Staphylococcus aureus KARI and yielded crystals that diffracted to 1.6-2.0 ? resolution. Prodrugs of these compounds possess antimycobacterial activity against H37Rv, a virulent strain of human TB, with the most active compound having an MIC90 of 2.32 ± 0.04 μM. This compound demonstrates a very favorable selectivity window and represents a highly promising lead as an anti-TB agent.

Phyllosilicate-derived Nickel-cobalt Bimetallic Nanoparticles for the Catalytic Hydrogenation of Imines, Oximes and N-heteroarenes

The development of cost-effective, noble metal-free catalytic systems for the hydrogenation of unsaturated aliphatic, aromatic, and heterocyclic compounds is fundamental for future valorization of general feedstock. With this aim, we report here the preparation of highly dispersed bimetallic Ni/Co nanoparticles (NPs), by a one-pot deposition-precipitation of Ni and Co phases onto mesoporous SBA-15 silica. By adjusting the chemical composition in the starting mixture, three supported catalysts with different Ni to Co weight ratios were obtained, which were further subjected to treatments under reducing conditions at high temperatures. Characterization of the resulting solids evidenced a homogenous distribution of Ni and Co elements forming the NPs, the best results being obtained for Ni/Co-2 : 2 samples, for which 50 wt.percent Ni–50 wt.percent Co NPs are found located on the surface of the residual phyllosilicate. Ni/Co-2 : 2, presenting the best performances for the hydrogenation of 2-methyl-quinoline, was further evaluated in the catalytic hydrogenation of selected imines, oximes and N-heteroarenes. Due to the high dispersion of bimetallic Ni?Co NPs, excellent properties (activity and selectivity) in the conversion of the selected substrates are reported.

Chiral N-hydroxybenzamides as potential catalysts for aerobic asymmetric oxidations

Chiral N-hydroxybenzamides (1H-3H) have been synthesized as precursors of chiral short-lived N-oxyl radicals 1?-3?. The latter species have been generated by oxidation of 1H-3H with Pb(OAc)4 or hydrogen abstraction from 1H-3H by the tert-butoxyl radical and characterized by UV-vis spectrophotometry and EPR spectroscopy. Through a kinetic study of the hydrogen atom transfer processes promoted by 1?-3? from three chiral benzylic substrates (1-phenylethylamine, 1-phenylethanol, and α-vinylbenzyl alcohol), a moderate chiral discrimination has been found, with selectivity factors 0.5 ≥ kH(S)/kH(R) ≥ 2.

B(C6F5)3-catalyzed hydrogenation of oxime ethers without cleavage of the N-O bond

The hydrogenation of oximes and oxime ethers is usually hampered by N-O bond cleavage, hence affording amines rather than hydroxylamines. The boron Lewis acid B(C6F5)3 is found to catalyze the chemoselective hydrogenation

A simple protocol for NMR analysis of the enantiomeric purity of chiral hydroxylamines

A practically simple three-component chiral derivatization protocol for determining the enantiopurity of chiral hydroxylamines by 1H NMR spectroscopic analysis is described, involving their treatment with 2-formylphenylboronic acid and enantiopure BINOL to afford a mixture of diastereomeric nitrono-boronate esters whose ratio is an accurate reflection of the enantiopurity of the parent hydroxylamine.

The mechanism of the α-ketoacid-hydroxylamine amide-forming ligation

Three-ring circus! Surprisingly complex molecular acrobatics are observed in the mechanism of the α-ketoacid-hydroxylamine amide-forming ligation reaction. Although this remarkable reaction can already be used for the chemoselective union of large, unprotected peptide fragments the elucidated mechanism provides important clues to extending its application to larger and more complex biological targets. Copyright

On the origins of diastereoselectivity in the alkylation of enolates derived from N-1-(1′-Naphthyl)ethyl-O-tert-butylhydroxamates: Chiral Weinreb amide equivalents

(Chemical Equation Presented) The stereochemical outcome observed upon alkylation of enolates derived from N-1-(1′-naphthyl)ethyl-O-tert- butylhydroxamates (chiral Weinreb amide equivalents) may be rationalized by a chiral relay mechanism. Deprotonation withKHMDS leads to a nonchelated (Z)-enolate inwhich the oxygen atoms adopt an anti-periplanar conformation. The configuration of the N-1-(1′-naphthyl)ethyl group dictates the conformation of the O-tert-butyl group and the configuration adopted by the adjacent pyramidal nitrogen atom. Highly diastereoselective enolate alkylation then proceeds anti to both the bulky tert-butyl group (sterically driven) and the N-lone pair (stereoelectronically driven).

Intermolecular Cope-type hydroamination of alkenes and alkynes using hydroxylamines

The development of the Cope-type hydroamination as a method for the metal- and acid-free intermolecular hydroamination of hydroxylamines with alkenes and alkynes is described. Aqueous hydroxylamine reacts efficiently with alkynes in a Markovnikov fashion to give oximes and with strained alkenes to give N-alkylhydroxylamines, while unstrained alkenes are more challenging. N-Alkylhydroxy-lamines also display similar reactivity with strained alkenes and give modest to good yields with vinylarenes. Electron-rich vinylarenes lead to branched products while electron-deficient vinylarenes give linear products. A beneficial additive effect is observed with sodium cyanoborohydride, the extent of which is dependent on the structure of the hydroxylamine. The reaction conditions are found to be compatible with common protecting groups, free OH and NH bonds, as well as bromoarenes. Both experimental and theoretical results suggest the proton transfer step of the N-oxide intermediate is of vital importance in the intermolecular reactions of alkenes. Details are disclosed concerning optimization, reaction scope, limitations, and theoretical analysis by DFT, which includes a detailed molecular orbital description for the concerted hydroamination process and an exhaustive set of calculated potential energy surfaces for the reactions of various alkenes, alkynes, and hydroxylamines.

Intermolecular cope-type hydroamination of alkenes and alkynes

(Chemical Equation Presented) Keep it simple! Intermolecular hydroamination can be achieved simply upon heating alkynes and alkenes with aqueous hydroxylamine. Alkynes react to afford oximes in good to excellent yields, and the formation of Markovnikov products is favored. A mechanism involving Cope-type hydroamination followed by bimolecular proton transfer is suggested and supported by DFT studies.

Phase-transfer catalysis for the synthesis of hydroxylamines from oximes using benzyltriethylammonium borohydride in methanol and under solid-phase conditions

Effective phase-transfer catalysis methodologies for the reduction of oximes to hydroxylamines by a selective and versatile reducing agent, benzyltriethylammonium borohydride (BTEABH), in methanol and under solid-phase conditions are presented.