24171-78-6

Basic information

• Product Name: Benzenamine, 3-bromo-N-hydroxy-
• CAS NO: 24171-78-6
• Molecular Formula: C6H6BrNO
• Molecular Weight: 188.024
• Mol File: 24171-78-6.mol
• Article Data: 11

Chemical Properties

• CAS DataBase Reference: Benzenamine, 3-bromo-N-hydroxy-(CAS DataBase Reference)
• NIST Chemistry Reference: Benzenamine, 3-bromo-N-hydroxy-(24171-78-6)
• EPA Substance Registry System: Benzenamine, 3-bromo-N-hydroxy-(24171-78-6)

Safety Data

• Hazardous Substances Data: 24171-78-6(Hazardous Substances Data)

Upstream product

• 1062320-38-0 C₁₁H₈BrNO₂ 
• 109-77-3 malononitrile 
• 585-79-5 m-nitrobromobenzene 

Downstream Products

• 114838-63-0 C₈H₈BrNO₂ 
• 13125-68-3 1-bromo-3-nitrosobenzene 
• 16750-67-7 4-amino-2-bromophenol 
• 23377-24-4 bis-(3-bromo-phenyl)-diazene-N-oxide 
• 868656-97-7 6-bromo-1H-indole-3-carboxylic acid methyl ester 
• 101909-43-7 4-bromo-1H-indole-3-carboxylic acid methyl ester 
• 1218786-51-6 N-methoxycarbonyl-N-(3-bromophenyl)hydroxylamine 

Relevant articles and documents

A general and scalable synthesis of polysubstituted indoles

A consecutive 2-step synthesis of N-unprotected polysubstituted indoles bearing an electron-withdrawing group at the C-3 position from readily available nitroarenes is reported. The protocol is based on the [3,3]-sigmatropic rearrangement of N-oxyenamines generated by the DABCO-catalyzed reaction of N-arylhydroxylamines and conjugated terminal alkynes, and delivers indoles endowed with a wide array of substitution patterns and topologies.

A Modified System for the Synthesis of Enantioenriched N-Arylamines through Copper-Catalyzed Hydroamination

Despite significant recent progress in copper-catalyzed enantioselective hydroamination chemistry, the synthesis of chiral N-arylamines, which are frequently found in natural products and pharmaceuticals, has not been realized. Initial experiments with N-arylhydroxylamine ester electrophiles were unsuccessful and, instead, their reduction in the presence of copper hydride (CuH) catalysts was observed. Herein, we report key modifications to our previously reported hydroamination methods that lead to broadly applicable conditions for the enantioselective net addition of secondary anilines across the double bond of styrenes, 1,1-disubstituted olefins, and terminal alkenes. NMR studies suggest that suppression of the undesired reduction pathway is the basis for the dramatic improvements in yield under the reported method.

Photoswitchable Magnetic Resonance Imaging Contrast by Improved Light-Driven Coordination-Induced Spin State Switch

We present a fully reversible and highly efficient on-off photoswitching of magnetic resonance imaging (MRI) contrast with green (500 nm) and violet-blue (435 nm) light. The contrast change is based on intramolecular light-driven coordination-induced spin state switch (LD-CISSS), performed with azopyridine-substituted Ni-porphyrins. The relaxation time of the solvent protons in 3 mM solutions of the azoporphyrins in DMSO was switched between 3.5 and 1.7 s. The relaxivity of the contrast agent changes by a factor of 6.7. No fatigue or side reaction was observed, even after >100 000 switching cycles in air at room temperature. Electron-donating substituents at the pyridine improve the LD-CISSS in two ways: better photostationary states are achieved, and intramolecular binding is enhanced.