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Usage

Uses

Used in Rare Metal Beneficiation:
Salicylhydroxamic acid is used as a collector for rare metal beneficiation, offering advantages such as good selectivity and strong collecting power. It is particularly effective in the separation and concentration of rare metal oxide minerals.
Used in Mineral Processing:
Salicylhydroxamic acid is utilized as a complexing agent or extractant in the processing of various ores, including rare earth ore, copper oxide ore, lead-zinc oxide ore, and gold ore. Its chelating properties enable efficient extraction and separation of valuable minerals from their ores.
Used in Organic Synthesis:
In addition to its applications in mineral processing, salicylhydroxamic acid also serves as an organic synthesis intermediate. This allows for the creation of a wide range of chemical compounds and products, further expanding its utility across various industries.

Preparation

synthesis of salicylhydroxamic acid: The ligand was prepared in two steps, step one the methyl salicylate was prepared by the esterification of salicylic acid with methanol in this reaction 28g (0.2 mol) of salicylic acid, 81cm3 of methanol and 8cm3 of concentrated sulfuric acid were mixed and step two by the coupling reaction of hydroxylamine and methyl salicylate. 13.9 g (0.2mol) of hydroxyl amine was weighed and added to 200cm3 of 10% sodium hydroxide solution and cooled at room temperature. Then 152.3g (0.1mol) of methyl salicylate was added in small portions with vigorous shaking after each addition to ensure complete dissolution. The mixture was allowed to stand for 36 hours. Then it was acidified with2M sulphuricacid and cooled. The precipitate was filtered, recrystallized from hot water containing a drop of acetic acid, recooled and filtered; white precipitate collected and weighed, the yield was salicylhydroxamic acid(14g).Preparation and Characterization of Salicylhydroxamic acid and its Complexes with Iron (III), Cobalt (II) and Manganese (II)

Purification Methods

Crystallise the hydroxamic acid from acetic acid. [Beilstein 10 H 98.]

InChI:InChI=1/C7H7NO3/c9-6-4-2-1-3-5(6)7(10)8-11/h1-4,9,11H,(H,8,10)

Upstream product

• 599-71-3 piloty's acid 
• 90-02-8 salicylaldehyde 
• 1441-87-8 salicyloyl chloride 
• 118-55-8 phenyl Salicylate 
• 118-61-6 2-hydroxy-benzoic acid ethyl ester 
• 5470-11-1 hydroxylamine hydrochloride 
• 69-72-7 salicylic acid 
• 55142-16-0 methyl 2-(benzyloxy)benzoate 
• 14389-86-7 2-benzyloxybenzoic acid 
• 1148157-39-4 2-benzyloxy-N-hydroxybenzamide 
• 932380-41-1 N-(benzyloxy)-2-hydroxybenzamide 
• 119-36-8 methyl salicylate 

Downstream Products

• 5426-08-4 3-Hydroxy-2H-1,3-benzoxazin-2,4(3H)-dion 
• 199854-00-7 O-acetylsalicylhydroxamic acid 
• 23979-92-2 3-hydroxy-2-phenyl-2,3-dihydro-benzo[e][1,3]oxazin-4-one 
• 101905-22-0 O-benzoyl-N-salicyloyl-hydroxylamine 
• 59-49-4 2-Benzoxazolinone 
• 69-72-7 salicylic acid 
• 35763-16-7 3.5-Dibrom-salicylhydroxamsaeure 
• 100-02-7 4-nitro-phenol 
• 14609-74-6 p-nitrophenolate 
• 91155-89-4 Ni(II) salicylhydroxamate 

Relevant academic research and scientific papers

Hydroxamic acid and preparation method of hydroxamic acid salt

The invention discloses a preparation method of hydroxamic acid salt. The preparation method comprises the following steps: mixing organic carboxylic ester, hydroxylamine or/and hydroxylamine salt, acatalyst and an inert solvent; and adding alkali and grinding to obtain the hydroxamic acid salt, and adding acid into the hydroxamic acid salt, grinding, centrifuging or filtering to obtain the hydroxamic acid. The process conditions for producing the hydroxamic acid or the hydroxamic acid salt by a grinding method in the prior art are optimized, the inert solvent diesel oil is used for replacingwater or methanol and the inert solvent is recycled after being subjected to centrifugal separation and simple treatment so that the generation of waste liquid is avoided, the use of toxic solvents is avoided and the operation safety is also greatly improved; besides, the material is in a flowing state during the grinding reaction due to the use of the inert solvent,so that the viscous material is prevented from adhering to the inner wall of the reaction container and the grinding medium, the reaction is more uniform, the temperature is more controllable, the reaction efficiency is greatly improved, the discharging is more convenient and the industrial production is facilitated.

Method for synthesizing hydroximic acid compound

The invention discloses a method for synthesizing a hydroximic acid compound. The method comprises the step of subjecting an organic carboxylic acid compound with a structure represented by a formula(I) shown in the description and a hydroxylamine compound with a structure represented by a formula (II) shown in the description to a grinding reaction in the presence of a coupling reagent, therebypreparing the hydroximic acid compound with a structure represented by a formula (III) shown in the description. According to the method, the technical problems that a large amount of organic solventis used, the reaction temperature is high, wastes are plenty, the aftertreatment is complicated, environmental protection is adverse and the like are solved, and the method has the advantages that thesource of the raw materials is wide, the cost is low, the operation is simple, the efficiency is high, the product is easy to separate, the yield is high, industrial production is easy to achieve andthe like.

Photoinduced one-pot synthesis of hydroxamic acids from aldehydes through in-situ generated silver nanoclusters

Hydroxamic acids have attracted significant attention due to their widespread use in applied chemistry. In this report, a modified Angeli–Rimini method has been achieved via the visible light-mediated catalytic transformation of a variety of heterocyclic, aromatic and aliphatic aldehydes 1a–j to their corresponding hydroxamic acids 2a–j in 81–93% yield. The unique ability of vitamin K3 as a photoredox catalyst to expedite the development of completely new reaction mechanisms and to enable the construction of challenging carbon–nitrogen bonds has been investigated. It is shown for the first time that the vitamin K3 and aldehyde are largely responsible for rapid in situ reduction of Ag+ ions to catalytic photoluminescent Ag nanoclusters that possess a bandgap energy of 2.87?eV and are less than 2 nm in size. A mechanism for this reaction has been proposed and is supported by UV–Vis, TEM, ESI/MS, FT-IR, 1H NMR and 13C NMR analyses. The investigated method utilizes readily available reagents and produces the hydroxamic acids in high yields without the formation of side products, making it simple, practical and cost-effective.

Synthesis and biological activity of salinomycin-hydroxamic acid conjugates

Several salinomycin-hydroxamic acid conjugates were designed and synthesized. Most conjugates showed better antiproliferative activities than salinomycin in HT-29 colon cancer, HGC-27 gastric cancer, and especially in MDA-MB-231 triple-negative human breast cancer cells. These conjugates are stable in cell culture media, and they showed much better biological activities than the 1:1 physical mixture with hydroxamic acids and salinomycin. The better membrane permeability and hydrolysis rate of the conjugates may lead to the activity improvements.

Benzoic hydroxamate-based iron complexes as model compounds for humic substances: Synthesis, characterization and algal growth experiments

A series of monomeric and dimeric FeIII complexes bearing benzoic hydroxamates as O,O-chelates has been prepared and characterized by elemental analysis, IR spectroscopy, UV-Vis spectroscopy, electrospray ionization mass spectrometry (ESI-MS), cyclic voltammetry, EPR spectroscopy and for some examples by X-ray diffraction analysis. The stability of the synthesized complexes in pure water and seawater was monitored over 24 h by means of UV-Vis spectrometry. The ability to release iron from the synthesized model complexes has been investigated with algae growth experiments.

Chromatography-free, Mitsunobu-triggered heterocyclizations of salicylhydroxamic acids to 3-hydroxybenzisoxazoles

The Mitsunobu reaction has become one of the most powerful tools to alkylate acidic pronucleophiles. A significant caveat of Mitsunobu chemistry, however, is that the reaction mixture is often plagued with purification problems owing to the phosphine oxide and hydrazine dicarboxylate by-products. In addition to the development of more readily separable Mitsunobu reagents, the product's physicochemical properties may be exploited to facilitate purification. In this regard, we present a swift and efficient preparation of 3-hydroxybenzisoxazoles by the Mitsunobu-triggered heterocyclizations of salicylhydroxamic acids, which can be isolated by an acid–base work-up. As expected, a range of functional groups was compatible with the chemistry.

Studies of spectral and magnetic behaviour of some complexes of Fe(II) metals with 2-hydroxy benzo-hydroxamic acid

Some complexes of Fe(II) cations with 2-hydroxy benzo- hydroxamic acid has been prepared separately in aqueous and non-aqueous medium. The general molecular formula of the complexes has been found to be [Fe(L)(B)4], where L= 2-hydroxy benzo-hydroxamic acid and B=bases containing oxygen and nitrogen atoms as their donor sites. On the characterisation of the complexes by usual physico-chemical methods, all the complexes have been found to be nonelectrolyte, monomeric and octahedral in geometry.

Synthesis and catalytic epoxidation potential of oxodiperoxo molybdenum(VI) complexes with 2-hydroxybenzohydroxamate and 2-hydroxybenzoate: The crystal structure of PPh4[MoO(O2)2(HBA)]

(PPh4)2[MoO(O2)2(SHAH)] ·H2O and PPh4[MoO-(O2)2(HBA)] (SHAH3 = 2-hydroxybenzohydroxamic acid and HBAH = 2-hydroxybenzoic acid) have been synthesized and characterized by physico-chemical and spectroscopic methods. In addition, the second complex has been structurally characterized by single-crystal X-ray diffraction analysis. We have compared the catalytic activities of these two new complexes, together with the previously reported PPh4[MoO(O2)2(BZ)] (BZH = benzoic acid), with respect to the epoxidation of alkenes. The hydroxamate complex is the most efficient catalyst among the three complexes, showing excellent catalytic activity for the substrates cyclohexene, cyclooctene, cinnamyl alcohol, pent-4-en-1-ol and hex-1-ene. Springer Science+Business Media B.V. 2010.

Inhibitors of the FEZ-1 metallo-β-lactamase

Metallo-β-lactamases (MBLs) catalyze the hydrolysis of β-lactams including penicillins, cephalosporins and carbapenems. Starting from benzohydroxamic acid (1) structure-activity studies led to the identification of selective inhibitors of the FEZ-1 MBL, e.g., 2,5-substituted benzophenone hydroxamic acid 17 has a Ki of 6.1 ± 0.7 μM against the FEZ-1 MBL but does not significantly inhibit the IMP-1, BcII, CphA or L1 MBLs.

BENZISOXAZOLES

The present invention concerns the compounds of formula (I), the N-oxide forms, the pharmaceutically acceptable addition salts and the stereochemically isomeric forms thereof, wherein m represents an integer from 1 to 3; X represents amino, hydroxy, -oxo or -Z-R1; Y is absent when X represents -Z-R1 and -(C=O)-R66 when X represents oxo; Z represents carbonyl, -oxy-carbonyl- or -NR 55-carbonyl-; R1 represents C1-4alkyl, Ar1, Ar1-C1-4a1ky1-, -NR3R4 or -Het1; R2 represents hydrogen, halo, nitro, hydroxycarbonyl-, C1-4alkyloxy or C1-4alkyl; R33 and R4 are each independently selected from hydrogen, Ar33 or C1-4alkyl; R5 represents hydrogen, C1-4alkylcarbonyl- or Ar4-carbonyl-; R6 represents a substituent selected from the group consisting of C1.4alkyl, Ar55, Ar6-C1-4alkyl- or NR7R8; R7 and R8 are each independently selected from hydrogen, Het4 or C1-4alkyl; Het1 represents a heterocycle selected from oxazolyl, isoxazolyl, imidazolyl or pyrazolyl wherein said heterocycle is optionally substituted with one, two or three substituents selected from the group consisting of amino, C1-4alkyl, hydroxy-C1-4alkyl, phenyl, phenyl-C1-4alkyl- and phenyl substituted with one or more halo substituents; Het4 represents a heterocycle selected from oxazolyl or isoxazolyl, wherein said heterocycle is optionally substituted with one or more substituents selected from the group consisting of amino, C1-4alkyl, hydroxy-C1-4alkyl-, phenyl, phenyl-Cl-4alkyl and phenyl substituted with one or more halo substituents; and Ar1, Ar2, Ar3, Ar4, Ar5 or Ar6 each independently represents phenyl optionally substituted one or where possible two or more substituents selected from halo, nitro, C1-4alkyl, hydroxy or C1-4alkyloxy-.