2594-06-1

Usage

Chemical Class

Hydroxamic acids

Derivative of

Acetohydroxamic acid

Chelating agent

Used in the treatment of urinary tract infections and to enhance the effectiveness of antibiotics

Modification

The addition of a 4-methoxyphenyl group to the acetohydroxamic acid molecule

Potential uses

Not fully understood, may be different from acetohydroxamic acid

Biological activity

Not fully understood, requires further research

Chemical structure

2-(4-methoxyphenyl)acetohydroxamic acid

Upstream product

• 123331-31-7 1-(1H-imidazol-1-yl)-2-(4-methoxyphenyl)ethan-1-one 
• 104-01-8 4-Methoxyphenylacetic acid 
• 14062-18-1 ethyl p-methoxyphenylacetate 

Downstream Products

• 104-47-2 p-methoxybenzylnitrile 
• 83196-19-4 9,10-dihydro-N-(4-methoxyphenylacetyl)-9,10-dimethyl-9,10-epoxyiminoanthracene 
• 7699-18-5 5-methoxyindolin-2-one 
• 7699-19-6 6-methoxyoxindole 
• 83196-21-8 N-(4-methoxybenzyl)-N’-phenylurea 
• 121726-58-7 N-Acetoxy-2-(4-methoxy-phenyl)-acetamide 

Relevant academic research and scientific papers

P(III)-Assisted Electrochemical Access to Ureas via in situ Generation of Isocyanates from Hydroxamic Acids

An external oxidant-free protocol for the generation of isocyanates from hydroxamic acids assisted by trivalent phosphine under mild electrochemical conditions was reported. The process started with the anodic oxidation of hydroxamic acids, followed by reacting with phosphine to form corresponding alkoxyphosphoniums and subsequent rearrangement with the release of tri-substituted phosphine oxide as the driving force to give isocyanates, which were trapped by N-based nucleophiles to produce various ureas. This method provides a broadly applicable procedure to access isocyanate intermediates under mild electrochemical conditions.

Synthesis of Lactams via Ir-Catalyzed C-H Amidation Involving Ir-Nitrene Intermediates

x-membered lactams were synthesized via either an amidation of sp3 C-H bonds or an electrophilic substitution of arenes via Ir-nitrene intermediates. With the employment of a readily available iridium catalyst in dichloromethane or hexafluoro-2-propanol, a wide range of lactams were synthesized in good to excellent yields with high selectivity.

Revisiting Arene C(sp2)?H Amidation by Intramolecular Transfer of Iridium Nitrenoids: Evidence for a Spirocyclization Pathway

Two mechanistic pathways, that is, electrocyclization and electrophilic aromatic substitution, are operative in most intramolecular C?H amination reactions proceeding by metal nitrenoid catalysis. Reported here is an alternative mechanistic scaffold leading to benzofused δ-lactams selectively. Integrated experimental and computational analysis revealed that the reaction proceeds by a key spirocyclization step followed by a skeletal rearrangement. Based on this mechanistic insight, a new synthetic route to spirolactams has been developed.

An Environmentally Sustainable Mechanochemical Route to Hydroxamic Acid Derivatives

An operationally simple, and cost efficient conversion of carboxylic acids into hydroxamic acid derivatives via a high-energy mechanochemical activation is presented. This ball milling methodology was applied to a wide variety of carboxylic acids dramatically improving purification issues associated with this class of molecules, which still remain one of the main bottlenecks of classical methodologies. (Figure presented.).

Direct Conversion of Hydroxamic Acids into Nitriles

Aromatic and aliphatic nitriles are prepared in excellent yield from the corresponding hydroxamic acids and phosphorus tribromide in benzene solution.