1629-17-0

Basic information

• Product Name: Benzamide, N-(2-bromo-5-fluorophenyl)-
• CAS NO: 1629-17-0
• Molecular Formula: C13H9BrFNO
• Molecular Weight: 294.123
• Mol File: 1629-17-0.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: Benzamide, N-(2-bromo-5-fluorophenyl)-(CAS DataBase Reference)
• NIST Chemistry Reference: Benzamide, N-(2-bromo-5-fluorophenyl)-(1629-17-0)
• EPA Substance Registry System: Benzamide, N-(2-bromo-5-fluorophenyl)-(1629-17-0)

Safety Data

• Hazardous Substances Data: 1629-17-0(Hazardous Substances Data)

Upstream product

• 1003-99-2 2-bromo-5-fluoroaniline 
• 98-88-4 benzoyl chloride 
• 2369-20-2 N-(3-fluorophenyl)hydroxylamine 
• 402-67-5 3-fluoro-1-nitrobenzene 

Relevant articles and documents

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.

Parallel synthesis of a library of benzoxazoles and benzothiazoles using ligand-accelerated copper-catalyzed cyclizations of ortho-halobenzanilides

A general method for the formation of benzoxazoles via a copper-catalyzed cyclization of ortho-haloanilides is reported. This approach complements the more commonly used strategies for benzoxazole formation which require 2-aminophenols as substrates. The reaction involves an intramolecular C-O cross-coupling of the ortho-haloanilides and is believed to proceed via an oxidative insertion/reductive elimination pathway through a Cu(I)/Cu(III) manifold. The reaction is also applicable to the formation of benzothiazoles. A variety of ligands including 1,10-phenanthroline and N,N′- dimethylethylenediamine were shown to provide ligand acceleration/stabilization in the reaction. Optimal conditions for cyclization used a catalyst combination of CuI and 1,10-phenanthroline (10 mol %). The method was amenable to a parallel-synthesis approach, as demonstrated by the synthesis of a library of benzoxazoles and benzothiazoles substituted at various positions in the ring. Most examples utilized the cyclization of ortho-bromoanilides, but orthoiodoanilides and ortho-chloroanilides also undergo a reaction under these conditions. The rate of reaction of the ortho-haloanilides follows the order I > Br > Cl, consistent with oxidative addition being the rate-determining step.