2614-48-4

Upstream product

• 4229-44-1 N-methylhydroxyamine hydrochloride 
• 100-07-2 4-methoxy-benzoyl chloride 
• 52898-56-3 N_.O-Dianisoyl-N-methyl-hydroxylamin 
• 593-77-1 N-Methylhydroxylamine 

Downstream Products

• 84927-92-4 dioxobis(N-methyl-p-anisoylhydroxamato)molybdenum(VI) 
• 121-98-2 methyl 4-methoxybenzoate 
• 100-09-4 4-methoxybenzoic acid 
• 3400-22-4 4-methoxy-N-methylbenzamide 
• 52898-49-4 4,N-dimethoxy-N-methylbenzamide 

Relevant academic research and scientific papers

Unexpected Z/E isomerism of N-methyl-O-phosphothioyl benzohydroxamic acids, their oxyphilic reactivity and inertness to amines

Thiophosphinoylation of N-methyl p-substituted benzohydroxamic acids using disulfanes (method A) or diphenylphosphinothioyl chloride (method B) provides only one conformer of the respective O-phosphothioyl derivative (X-ray and NMR analysis). Undergoing t

Late-Stage Photoredox C-H Amidation of N-Unprotected Indole Derivatives: Access to N-(Indol-2-yl)amides

The late-stage functionalization of N-unprotected indoles can be useful for modifying low-molecular-weight drugs and bioactive peptides. Whereas indole carboxamides are valuable in pharmaceutical applications, the preparation N-(indol-2-yl)amides with similar structures continues to be challenging. Herein we report on visible-light-induced late-stage photoredox C-H amidation with N-unprotected indoles and tryptophan-containing peptides, leading to the formation of N-(indol-2-yl)amide derivatives. N-Unprotected indoles and aryloxyamides that contain an electron-withdrawing group could be coupled directly to eosin Y as the photocatalyst by irradiation with a green light-emitting diode at room temperature. Mechanistic studies and density functional theory calculations indicate that the transformation might proceed through the oxidative C-H functionalization of indole with a PS? to PS?- cycle. This protocol provides a new toolkit for the late-stage modification labeling and peptide-drug conjugation of N-unprotected indole derivatives.

Oxidative cleavage of hydroxamic acid promoted by sodium periodate

A series of hydroxamic acids, involving aliphatic, aromatic and cyclic substrates, were transformed to the corresponding carboxylic acids through NaIO4-mediated oxidative cleavage in mild conditions. Esterification of these acids with TMSCHN2 could result in formation of the corresponding methyl ester. This methodology makes good compensation for the existing methods transforming amides to esters. Our results also pave the way to harness hydroxamic acids as useful synthetic building blocks.

Determination of pKa's of hydroxamic acids by nucleophilic substitution reaction

Acid dissociation constant (pKa) of some para-substituted benzohydroxamic, 4-XC6H4CONHOH, and N-methyl para-substituted benzohydroxamic acids, 4- XC6H4CON(OH) CH3, where X = H, CH3, CH3O, NO2, Cl, have been determined spectrophotometrically by nucleophilic substitution reactions of p-nitrophenyl acetate with hydroxamate ions at 27± 0.1°C. All reactions in this study follow pseudo-first order kinetics under condition of excess nucleophile. Good correlation has been observed between pKa and substitutent constants pointing out the validity of the Hammett equation. The kinetics results have been discussed on the basis of pKa and α-effect of hydroxamic acids.

Conformational behaviour of hydroxamic acids: Ab initio and structural studies

The conformational behaviour of a series of monohydroxamic acids, p-RC6H4CONR 'OH (R = Me, R' = H Me; R = MeO, R' = H, Me; R = NO2, R' = H), and a series of dihydroxamic acids, (CH2)n (CONR'OH)2 (n = 3-8, 10, R' = H and n = 7, R' = Me), in methanol, DMSO and chloroform and in the solid state has been examined using IR and NMR spectroscopy. X-Ray crystal structure determinations of p-MeC6H4CONMeOH and the monohydrate of glutarodihydroxamic acid (n = 3) together with ab initio molecular orbital calculations for several hydrated and unhydrated hydroxamic acids have been performed. Hydrogen bonding effects are shown to be important in both the so id state and solution. The cis(Z) conformation of the hydroxamate group(s) (CONHOH) is preferentially stabilized by hydrogen bonding with water molecules.

Polar ligand adsorption controls semiconductor surface potentials

Controlled surface modification of CdTe single crystals and CdTe and CulnSe2 solar cell quality thin films was achieved by chemisorption of a series of organic ligands with varying dipole moments. Contact potential difference measurements in air showed that adsorption of benzoic or hydroxamic acid derivatives on the thin films or crystals changes the semiconductors' electron affinity without significantly affecting band bending. The magnitude and direction of surface potential changes, which reach 670 mV between extreme modifications, correlate with the ligands' dipole moments. Ligand dipole moments were controlled by varying the substituents of the ligand. Quantitative Fourier transform infrared (FTIR) spectroscopy showed that benzoic acid surface coverage is about one monolayer. Finally, FTIR spectral analysis showed that the benzoic acid derivatives adsorb via coordination to Cd on CdTe and that hydroxamic acids bind to Cd on CdTe and to In on CuInSe2. These phenomena occur in several systems (two semiconductor compounds, two types of binding groups, and two types of surface morphologies were examined) and may prove useful in band edge engineering.