3827-49-4

Usage

Chemical Properties

clear colourless to pale yellow liquid

InChI:InChI=1/C5H5F3O2/c1-3(4(9)10-2)5(6,7)8/h1H2,2H3

Upstream product

• 372-20-3 3-fluorophenol 
• 372-19-0 meta-fluoroaniline 

Downstream Products

• 524955-92-8 2-chloro-5-fluoro-4-nitrophenol 
• 1034474-29-7 3-bromo-5-chlorophenyl 2-chloro-5-fluorophenyl ether 
• 1036762-60-3 C₉H₈ClFO₂ 
• 1345855-12-0 N-(5-chloro-2-fluoro-4-(3-(1-methyl-1H-pyrazol-4-yl)pyridin-4-yloxy)phenyl)-4-ethoxy-1-(4-fluorophenyl)-2-oxo-1,2-dihydropyridine-3-carboxamide 
• 1345854-99-0 5-chloro-2-fluoro-4-(3-(1-methyl-1H-pyrazol-4-yl)pyridin-4-yloxy)benzenamine 
• 1345854-97-8 4-(3-bromopyridin-4-yloxy)-5-chloro-2-fluorobenzenamine 
• 1345854-96-7 3-bromo-4-(2-chloro-5-fluoro-4-nitrophenoxy)pyridine 
• 1345854-95-6 3-bromo-4-(2-chloro-5-fluorophenoxy)pyridine 
• 1207669-20-2 2-chloro-5-fluorophenyl trifluoromethanesulfonate 
• 1169484-20-1 sodium 2-(5-chloro-2-fluoro-4-hydroxyphenyl)-2-hydroxyacetate 
• 1161026-05-6 1-chloro-4-fluoro-2-(4-nitrophenoxy)benzene 
• 1036383-21-7 4-bromo-2-chloro-5-fluoro-phenol 
• 944808-88-2 (3-[4-(2-chloro-5-fluorophenoxy)-1-piperidinyl]-6-(5-methyl-1,3,4-oxadiazol-2-yl)-pyridazine) 
• 944808-85-9 N'-acetyl-6-[4-(2-chloro-5-fluorophenoxy)piperidin-1-yl]pyridazine-3-carbohydrazine 

Relevant academic research and scientific papers

Catalyst-Controlled Regioselective Chlorination of Phenols and Anilines through a Lewis Basic Selenoether Catalyst

We report a highly efficient ortho-selective electrophilic chlorination of phenols utilizing a Lewis basic selenoether catalyst. The selenoether catalyst resulted in comparable selectivities to our previously reported bis-thiourea ortho-selective catalyst, with a catalyst loading as low as 1%. The new catalytic system also allowed us to extend this chemistry to obtain excellent ortho-selectivities for unprotected anilines. The selectivities of this reaction are up to >20:1 ortho/para, while the innate selectivities for phenols and anilines are approximately 1:4 ortho/para. A series of preliminary studies revealed that the substrates require a hydrogen-bonding moiety for selectivity.

Ammonium Salt-Catalyzed Highly Practical Ortho-Selective Monohalogenation and Phenylselenation of Phenols: Scope and Applications

An ortho-selective ammonium chloride salt-catalyzed direct C-H monohalogenation of phenols and 1,1′-bi-2-naphthol (BINOL) with 1,3-dichloro-5,5-dimethylhydantoin (DCDMH) as the chlorinating agent has been developed. The catalyst loading was low (down to 0.01 mol %) and the reaction conditions were very mild. A wide range of substrates including BINOLs were compatible with this catalytic protocol. Chlorinated BINOLs are useful synthons for the synthesis of a wide range of unsymmetrical 3-aryl BINOLs that are not easily accessible. In addition, the same catalytic system can facilitate the ortho-selective selenylation of phenols.

The Catalyst-Controlled Regiodivergent Chlorination of Phenols

Different catalysts are demonstrated to overcome or augment a substrate's innate regioselectivity. Nagasawa's bis-thiourea catalyst was found to overcome the innate para-selectivity of electrophilic phenol chlorination, yielding ortho-chlorinated phenols that are not readily obtainable via canonical electrophilic chlorinations. Conversely, a phosphine sulfide derived from 2,2′-Bis(diphenylphosphino)-1,1′-binaphthyl (BINAP) was found to enhance the innate para-preference of phenol chlorination.