14454-14-9

Basic information

• Product Name: N-hydroxy-4-iodoaniline
• Synonyms: benzenamine, N-hydroxy-4-iodo-; N-Hydroxy-4-iodoaniline
• CAS NO: 14454-14-9
• Molecular Formula: C₆H₆INO
• Molecular Weight: 235.0224
• Mol File: 14454-14-9.mol
• Article Data: 18

Chemical Properties

• Boiling Point: 292.2°C at 760 mmHg
• Flash Point: 130.5°C
• Density: 2.099g/cm³
• Vapor Pressure: 0.000853mmHg at 25°C
• Refractive Index: 1.751
• CAS DataBase Reference: N-hydroxy-4-iodoaniline(CAS DataBase Reference)
• NIST Chemistry Reference: N-hydroxy-4-iodoaniline(14454-14-9)
• EPA Substance Registry System: N-hydroxy-4-iodoaniline(14454-14-9)

Safety Data

• Hazardous Substances Data: 14454-14-9(Hazardous Substances Data)

Upstream product

• 636-98-6 p-nitrobenzene iodide 
• 540-37-4 p-aminoiodobenzene 

Downstream Products

• 110606-23-0 N-p-iodophenyl-2-furylacrylohydroxamic acid 
• 13125-93-4 1-iodo-4-nitrosobenzene 
• 96127-01-4 N-Hydroxy-N-(4-iodo-phenyl)-benzamide 
• 1360771-78-3 C₁₃H₉I₂NO₂ 
• 1609945-48-3 4-iodo-N-(4-methyl-2-methylenepent-3-enyl)benzeneamine 
• 175278-18-9 N-(4-bromo-2-(trifluoromethoxy)phenyl)acetamide 
• 67274-48-0 N-acetyl-N-(4-bromophenyl)hydroxylamine 
• 874814-76-3 N-(4-iodo-2-(trifluoromethoxy)phenyl)acetamide 
• 67274-49-1 N-hydroxy-N-(4-iodophenyl)acetamide 
• 1396396-19-2 ethyl 2-benzoyl-1-(4-iodophenyl)-5-phenyl-1H-pyrrole-3-carboxylate 

Relevant articles and documents

Synthesis and preliminary evaluation of a library of polycyclic small molecules for use in chemical genetic assays

(-)-Shikimic acid, 3, was converted into both enantiomers of epoxycyclohexenol carboxylic acid, 7, which were attached to a solid support via a photocleavable linker. Tandem acylation-1,3-dipolar cycloaddition with nitrones 11a-g yielded tetracyclic templates 12a-g. After development of several efficient coupling reactions of iodobenzyl tetracycles 12b-d and completion of extensive validation protocols, a splitpool synthesis yielded a binary encoded library calculated to contain 2.18 million polycyclic compounds. These compounds are compatible with miniaturized cell-based 'forward' chemical genetic assays designed to explore biological pathways and 'reverse' chemical genetic assays designed to explore protein function. As a simple illustration of the potential of these compounds, several were shown to activate a TGF-β-responsive reporter gene in mammalian cells.

Practical bromination of arylhydroxylamines with SOBr2 towards ortho-bromo-anilides

A facile approach for synthesizing ortho-bromoanilides from readily available aryhydroxylamines and thionyl bromide is demonstrated in this work. Mild reaction conditions and broad scope of substrates ranging from heterocyclic structures to pharmaceutics-potential motifs are used in the reactions of this paper. Efficient bromination of ortho C–H bonds of the aryhydroxylamines has been achieved. Ortho-bromoanilide products were obtained in good to excellent yields, and model scaled-up reactions of this synthetic approach are shown in this work.

Bi(I)-Catalyzed Transfer-Hydrogenation with Ammonia-Borane

A catalytic transfer-hydrogenation utilizing a well-defined Bi(I) complex as catalyst and ammonia-borane as transfer agent has been developed. This transformation represents a unique example of low-valent pnictogen catalysis cycling between oxidation states I and III, and proved useful for the hydrogenation of azoarenes and the partial reduction of nitroarenes. Interestingly, the bismuthinidene catalyst performs well in the presence of low-valent transition-metal sensitive functional groups and presents orthogonal reactivity compared to analogous phosphorus-based catalysis. Mechanistic investigations suggest the intermediacy of an elusive bismuthine species, which is proposed to be responsible for the hydrogenation and the formation of hydrogen.