67274-49-1

Basic information

• Product Name: N-hydroxy-N-(4-iodophenyl)acetamide
• Synonyms: Acetamide, N-hydroxy-N-(4-iodophenyl)-
• CAS NO: 67274-49-1
• Molecular Formula: C₈H₈INO₂
• Molecular Weight: 277.0591
• Mol File: 67274-49-1.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 358.4°C at 760 mmHg
• Flash Point: 170.5°C
• Density: 1.922g/cm³
• Vapor Pressure: 9.27E-06mmHg at 25°C
• Refractive Index: 1.689
• CAS DataBase Reference: N-hydroxy-N-(4-iodophenyl)acetamide(CAS DataBase Reference)
• NIST Chemistry Reference: N-hydroxy-N-(4-iodophenyl)acetamide(67274-49-1)
• EPA Substance Registry System: N-hydroxy-N-(4-iodophenyl)acetamide(67274-49-1)

Safety Data

• Hazardous Substances Data: 67274-49-1(Hazardous Substances Data)

Upstream product

• 14454-14-9 N-(4-iodophenyl)hydroxylamine 
• 75-36-5 acetyl chloride 
• 636-98-6 p-nitrobenzene iodide 

Downstream Products

• 874814-76-3 N-(4-iodo-2-(trifluoromethoxy)phenyl)acetamide 

Relevant articles and documents

Hydroxamic Acids as Chemoselective (ortho-Amino)arylation Reagents via Sigmatropic Rearrangement

The use of readily available hydroxamic acids as reagents for the chemoselective (ortho-amino)arylation of amides is described. This reaction proceeds under metal-free, mild conditions, displays a very broad scope, and constitutes a direct approach for the metal-free attachment of aniline residues to carbonyl derivatives.

Mechanistic studies on intramolecular C-H trifluoromethoxylation of (hetero)arenes via OCF3-migration

The one-pot two-step intramolecular aryl and heteroaryl C-H trifluoromethoxylation recently reported by our group has provided a general, scalable, and operationally simple approach to access a wide range of unprecedented and valuable OCF3-containing building blocks. Herein we describe our investigations to elucidate its reaction mechanism. Experimental data indicate that the O-trifluoromethylation of N-(hetero)aryl-N-hydroxylamine derivatives is a radical process, whereas the OCF3-migration step proceeds via a heterolytic cleavage of the N-OCF3 bond followed by rapid recombination of a short-lived ion pair. Computational studies further support the proposed ion pair reaction pathway for the OCF3-migration process. We hope that the current study would provide useful insights for the development of new transformations using versatile N-(hetero)aryl-N-hydroxylamine synthons.