16238-03-2

Basic information

• Product Name: 2-phenyl-5-(trifluoromethyl)benzofuran
• Synonyms: 2-phenyl-5-(trifluoromethyl)benzofuran
• CAS NO: 16238-03-2
• Molecular Weight: 262.231
• Mol File: 16238-03-2.mol

Chemical Properties

• CAS DataBase Reference: 2-phenyl-5-(trifluoromethyl)benzofuran(CAS DataBase Reference)
• NIST Chemistry Reference: 2-phenyl-5-(trifluoromethyl)benzofuran(16238-03-2)
• EPA Substance Registry System: 2-phenyl-5-(trifluoromethyl)benzofuran(16238-03-2)

Safety Data

• Hazardous Substances Data: 16238-03-2(Hazardous Substances Data)

Upstream product

• 100-52-7 benzaldehyde 
• 886496-63-5 1-bromo-2-(bromomethyl)-4-(trifluoromethyl)benzene 
• 869725-53-1 (2-bromo-5-(trifluoromethyl)phenyl)methanol 
• 1483-56-3 2-bromo-5-(trifluoromethyl)benzoic acid 
• 128796-39-4 4-trifluoromethylphenylboronic acid 
• 155590-65-1 C₁₁H₁₂F₃NO₂ 
• 98-86-2 acetophenone 
• 463976-21-8 α,α,α-trifluoro-o-iodo-p-cresol 
• 536-74-3 phenylacetylene 

Relevant articles and documents

Strategy for Overcoming Full Reversibility of Intermolecular Radical Addition to Aldehydes: Tandem C-H and C-O Bonds Cleaving Cyclization of (Phenoxymethyl)arenes with Carbonyls to Benzofurans

An intermolecular addition of carbon radicals enabled by a cascade radical coupling strategy is developed. It includes an intermolecular alkyl radical addition to a carbonyl group followed by an intramolecular alkoxy radical addition to haloarenes and produces substituted benzofurans in high yields. The radical nature of this reaction is explored by radical trapping experiments and EPR analysis. The mechanism is investigated by KIE experiments and control experiments. This method could provide rapid and practical access to the key intermediate of TAM-16, a safe and potent antibacterial agent for treating tuberculosis, and, therefore, is of great importance for organic synthesis and the pharmaceutical industry.

Copper pincer complexes as advantageous catalysts for the heteroannulation of ortho-halophenols and alkynes

A new, non-symmetrical copper(II) pincer complex catalyzes much more efficiently the formation of benzofuran by the reaction between ortho-iodophenols and alkynes. The lowest catalyst loadings are realized for this reaction, and bromo- and chlorophenols are heteroannulated for the first time. Strong evidence for hydrophenoxylation and intramolecular halogen atom-transfer steps catalyzed by this remarkably active, recyclable homogeneous catalyst is provided.

Metal-free one-pot synthesis of benzofurans

Ethyl acetohydroxamate was efficiently arylated with diaryliodonium salts at room temperature under transition-metal-free conditions. The obtained O-arylated products were reacted in situ with ketones under acidic conditions to yield substituted benzo[b]furans through oxime formation, [3,3]-rearrangement, and cyclization in a fast and operationally simple one-pot fashion without using excess reagents. Alternatively, the O-arylated products could be isolated or transformed in situ to aryloxyamines or O-arylaldoximes. The methodology was applied to the synthesis of Stemofuran A and the formal syntheses of Coumestan, Eupomatenoid 6, and (+)-machaeriol B. Just add salt! A metal-free, room temperature arylation of ethyl acetohydroxamate, followed by an in situ reaction with ketones under acidic conditions yielded substituted benzo[b]furans in a fast and operationally simple one-pot fashion without using excess reagents (see scheme). Alternatively, the O-arylated products could be isolated, hydrolyzed in situ to aryloxyamines, or transformed to O-arylaldoximes. The efficiency of the methodology was demonstrated by the formal synthesis of several biologically active benzofurans.