328081-49-8

Basic information

• Product Name: (p-bromo-N-phenoxy)phthalimide
• Synonyms: (p-bromo-N-phenoxy)phthalimide
• CAS NO: 328081-49-8
• Molecular Weight: 318.126
• Mol File: 328081-49-8.mol
• Article Data: 21

Chemical Properties

• CAS DataBase Reference: (p-bromo-N-phenoxy)phthalimide(CAS DataBase Reference)
• NIST Chemistry Reference: (p-bromo-N-phenoxy)phthalimide(328081-49-8)
• EPA Substance Registry System: (p-bromo-N-phenoxy)phthalimide(328081-49-8)

Safety Data

• Hazardous Substances Data: 328081-49-8(Hazardous Substances Data)

Upstream product

• 524-38-9 N-hydroxyphthalimide 
• 5467-74-3 4-Bromophenylboronic acid 

Downstream Products

• 107986-49-2 N-(5-bromo-2-hydroxyphenyl)acetamide 
• 55082-33-2 5-bromo-2-hydroxybenzophenone 
• 945531-29-3 5-bromo-2-(p-tolyl)benzo[d]oxazole 
• 1107023-88-0 5-bromo-2-(4-methoxyphenyl)benzo[d]oxazole 
• 1310486-79-3 C₁₁H₈BrNO₂ 
• 1310486-76-0 C₁₄H₁₂BrNO 
• 1310486-75-9 C₁₄H₁₂BrNO₂ 
• 1310486-74-8 C₁₃H₉BrClNO 
• 1268387-01-4 C₁₇H₁₂BrNO 
• 65440-82-6 O-(4-bromophenyl)hydroxylamine 

Relevant articles and documents

Rh(III)-Catalyzed Redox-Neutral Unsymmetrical C-H Alkylation and Amidation Reactions of N-Phenoxyacetamides

A Rh(III)-catalyzed unsymmetrical C-H alkylation and amidation of N-phenoxyacetamides with diazo compounds has been developed under mild and redox-neutral conditions, producing dinitrogen as the only byproduct. The reaction represents the first example of one-step, unsymmetrical difunctionalization of two ortho-C-H bonds. Experimental and computational studies support that N-phenoxyacetamides most likely undergo an initial ortho-C-H alkylation with diazo compounds via a Rh(III)-catalyzed C-H activation, and the resulting Rh(III) intermediate subsequently undergoes an intramolecular oxidative addition into the O-N bond to form a Rh(V) nitrenoid species that is protonated and further directed toward electrophilic addition to the second ortho position of the phenyl ring. This work might provide a new direction for unsymmetrical C-H difunctionalization reactions in an efficient manner.

Synthesis of ortho-phenolic sulfilimines via an intermolecular sulfur atom transfer cascade reaction

To expand the toolbox for the synthesis of ortho-phenolic sulfilimines, sigmatropic rearrangements were introduced to the field of sulfilimine chemistry. Herein we report a N-H sulfenylation/[2,3]-sigmatropic rearrangement cascade reaction. This mild reaction enables commercially available thiols to serve as the sulfenylation reagent and generates water as the sole byproduct. Moreover, the reaction has a wide substrate scope and can be conducted on a gram scale with excellent reaction efficiency.

An internal oxidant-directing strategy enabling transition metal-free C–S bond ligation

Organic sulfur compounds have broad applications in biology, medicine and material sciences and intensive efforts have been devoted to developing mild and general C–S bond-forming methods. However, a mild, transition-metal-free, direct C–H bond functionalization method remains elusive. Here, we report the use of an internal oxidant-directing strategy to achieve this goal. The cascade reactions described here show excellent chemoselectivity and a wide substrate scope for both oxyamines and sulfenylation reagents. This study enlarges the synthesis toolbox for preparing structurally diverse sulfilimines under mild conditions.