17698-15-6

Basic information

• Product Name: N-hydroxythiophene-2-carboxamide
• Synonyms: N-hydroxythiophene-2-carboxamide;2-Thiophenecarboxamide,N-hydroxy-(9CI)
• CAS NO: 17698-15-6
• Molecular Formula: C₅H₅NO₂S
• Molecular Weight: 143.16
• Product Categories: OXIME
• Mol File: 17698-15-6.mol
• Article Data: 17

Chemical Properties

• Boiling Point: °Cat760mmHg
• Flash Point: °C
• Appearance: /
• Density: 1.427g/cm³
• Refractive Index: 1.618
• CAS DataBase Reference: N-hydroxythiophene-2-carboxamide(CAS DataBase Reference)
• NIST Chemistry Reference: N-hydroxythiophene-2-carboxamide(17698-15-6)
• EPA Substance Registry System: N-hydroxythiophene-2-carboxamide(17698-15-6)

Safety Data

• Hazardous Substances Data: 17698-15-6(Hazardous Substances Data)

Usage

InChI:InChI=1/C5H5NO2S/c7-5(6-8)4-2-1-3-9-4/h1-3,8H,(H,6,7)

Upstream product

• 527-72-0 2-thiophenylcarboxylic acid 
• 5813-89-8 2-thiophenylcarboxamide 
• 5380-42-7 thiophene-2-carboxylic acid methyl ester 
• 1340546-32-8 diisopropyl 1-(thiophene-2-carbonyl)hydrazine-1,2-dicarboxylate 
• 83039-60-5 2,5-dioxopyrrolidin-1-yl thiophene-2-carboxylate 
• 5271-67-0 2-Thiophenecarbonyl chloride 
• 98-03-3 thiophene-2-carbaldehyde 

Downstream Products

• 2048-57-9 2-thiophene isocyanate 
• 1426922-74-8 N-(methyl(oxo)(phenyl)-λ⁶-sulfanylidene)thiophene-2-carboxamide 

Relevant articles and documents

Hydroxamates as a potent skeleton for the development of metallo-β-lactamase inhibitors

Bacterial resistance caused by metallo-β-lactamases (MβLs) has become an emerging public health threat, and the development of MβLs inhibitor is an effective way to overcome the resistance. In this study, thirteen novel O-aryloxycarbonyl hydroxamates were constructed and assayed against MβLs. The obtained molecules specifically inhibited imipenemase-1 (IMP-1) and New Delhi metallo-β-lactamase-1, exhibiting an IC50 value in the range of 0.10–18.42 and 0.23–22.33?μM, respectively. The hydroxamate 5 was found to be the most potent inhibitor, with an IC50 of 0.1 and 0.23?μM using meropenem and cefazolin as substrates. ICP-MS analysis showed that 5 did not coordinate to the Zn(II) ions at the active site of IMP-1, while the rapid dilution, thermal shift and MALDI-TOF assays revealed that the hydroxamate formed a covalent bond with the enzyme. Cytotoxicity assays indicated that the hydroxamates have low toxicity in MCF-7 cells. This work provided a potent scaffold for the development of MβLs inhibitors.

Silver-Catalyzed Acyl Nitrene Transfer Reactions Involving Dioxazolones: Direct Assembly of N-Acylureas

Dioxazolones and isocyanides are useful synthetic building blocks, and have attracted significant attention from researchers. However, the silver-catalyzed nitrene transfer reaction of dioxazolones has not been investigated to date. Herein, a silver-catalyzed acyl nitrene transfer reaction involving dioxazolones, isocyanides, and water was realized in the presence of Ag2O to afford a series of N-acylureas in moderate to good yields.

Synthesis of sulfimides and N-Allyl-N-(thio)amides by Ru(II)catalyzed nitrene transfer reactions of N-acyloxyamides

The N-acyloxyamides were employed as effective N-acyl nitrene precursors in reactions with thioethers under the catalysis of a commercially available Ru(II) complex, from which a variety of sulfimides were synthesized efficiently and mildly. If an allyl group is contained in the thioether precursor, the [2,3]-sigmatropic rearrangement of the sulfimide occurs simultaneously and the N-allyl-N-(thio)amides were obtained as the final products. Preliminary mechanistic studies indicated that the Ru-nitrenoid species should be a key intermediate in the transformation.