262587-05-3

Basic information

• Product Name: 3-(DIFLUOROMETHOXY)BROMOBENZENE
• Synonyms: 1-BROMO-3-(DIFLUOROMETHOXY)BENZENE;3-(DIFLUOROMETHOXY)BROMOBENZENE;Jrd-0474;3-BroMo-1-(difluoroMethoxy)benzene;Inter-bromo-difluoromethoxybenzene
• CAS NO: 262587-05-3
• Molecular Formula: C₇H₅BrF₂O
• Molecular Weight: 223.01
• Product Categories: Ethers;Organic Building Blocks;Oxygen Compounds;Fluorine series
• Mol File: 262587-05-3.mol

Chemical Properties

• Boiling Point: 196-197 °C(lit.)
• Flash Point: 199 °F
• Appearance: liquid
• Density: 1.585 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.54mmHg at 25°C
• Refractive Index: n20/D 1.502(lit.)
• Storage Temp.: Room temperature.
• CAS DataBase Reference: 3-(DIFLUOROMETHOXY)BROMOBENZENE(CAS DataBase Reference)
• NIST Chemistry Reference: 3-(DIFLUOROMETHOXY)BROMOBENZENE(262587-05-3)
• EPA Substance Registry System: 3-(DIFLUOROMETHOXY)BROMOBENZENE(262587-05-3)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36-37
• WGK Germany: 3
• HazardClass: IRRITANT
• Hazardous Substances Data: 262587-05-3(Hazardous Substances Data)

Usage

Chemical Properties

liquid

InChI:InChI=1/C7H5BrF2O/c8-5-2-1-3-6(4-5)11-7(9)10/h1-4,7H

Upstream product

• 591-20-8 3-Bromophenol 
• 1895-39-2 sodium chlorodifluoroacetate 
• 108-86-1 bromobenzene 
• 1435486-10-4 ethyl (3-bromophenoxy)(fluoro)acetate 
• 1432474-19-5 2-(3-bromophenoxy)-2-fluoroacetic acid 

Downstream Products

• 756752-48-4 tert-butyl 4-(3-difluoromethoxyphenyl)piperazin-1-ylcarboxylate 
• 1035690-56-2 2-(3-(difluoromethoxy)phenyl )-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 
• 1354286-44-4 N-(5-(3-(difluoromethoxy)phenyl)-2-morpholinopyridin-4-yl)-5,7-difluoro-3-methyl-2-(pyridin-2-yl)quinolin-4-amine 
• 1361046-27-6 4-(3-difluoromethoxyphenylthio)-2,5-xylidine 
• 1361044-69-0 N-ethyl-N-methyl-N'-[4-(3-difluoromethoxyphenylthio)-2,5-xylyl]formamidine 
• 1361046-19-6 2-nitro-5-(3-difluoromethoxyphenylthio)-p-xylene 
• 1439400-61-9 C₁₃H₁₆F₂O₃ 
• 262587-06-4 2-(3-(difluoromethoxy)phenyl)acetic acid 
• 1439399-52-6 C₂₇H₂₆F₂N₆O₃S 
• 1439399-54-8 C₂₇H₂₆F₂N₆O₃S 
• 866607-09-2 (3-(difluoromethoxy)phenyl)boronic acid 
• 1142224-93-8 (3'-((difluoromethyl)oxy)-2-(2,2-dimethylcyclopentyl)-1,1'-biphenyl-4-yl)methanol 
• 1142224-91-6 methyl 3'-((difluoromethyl)oxy)-2-(2,2-dimethylcyclopentyl)-1,1'-biphenyl-4-carboxylate 

Relevant articles and documents

Redox-Neutral TEMPO Catalysis: Direct Radical (Hetero)Aryl C?H Di- and Trifluoromethoxylation

Applications of TEMPO. catalysis for the development of redox-neutral transformations are rare. Reported here is the first TEMPO.-catalyzed, redox-neutral C?H di- and trifluoromethoxylation of (hetero)arenes. The reaction exhibits a broad substrate scope, has high functional-group tolerance, and can be employed for the late-stage functionalization of complex druglike molecules. Kinetic measurements, isolation and resubjection of catalytic intermediates, UV/Vis studies, and DFT calculations support the proposed oxidative TEMPO./TEMPO+ redox catalytic cycle. Mechanistic studies also suggest that Li2CO3 plays an important role in preventing catalyst deactivation. These findings will provide new insights into the design and development of novel reactions through redox-neutral TEMPO. catalysis.

Catalytic radical difluoromethoxylation of arenes and heteroarenes

Intermolecular C-H difluoromethoxylation of (hetero)arenes remains a long-standing and unsolved problem in organic synthesis. Herein, we report the first catalytic protocol employing a redox-active difluoromethoxylating reagent 1a and photoredox catalysts for the direct C-H difluoromethoxylation of (hetero)arenes. Our approach is operationally simple, proceeds at room temperature, and uses bench-stable reagents. Its synthetic utility is highlighted by mild reaction conditions that tolerate a wide variety of functional groups and biorelevant molecules. Experimental and computational studies suggest single electron transfer (SET) from excited photoredox catalysts to 1a forming a neutral radical intermediate that liberates the OCF2H radical exclusively. Addition of this radical to (hetero)arenes gives difluoromethoxylated cyclohexadienyl radicals that are oxidized and deprotonated to afford the products of difluoromethoxylation.

DIFLUOROMETHOXYLATION AND TRIFLUOROMETHOXYLATION COMPOSITIONS AND METHODS FOR SYNTHESIZING SAME

The present invention provides a compound having the structure (I), a processing of making the compound; and a process of using the compound as a reagent for the difluoromethoxylation and trifluoromethoxylation of arenes or heteroarenes.

Xenon Difluoride Mediated Fluorodecarboxylations for the Syntheses of Di- and Trifluoromethoxyarenes

XeF2 is demonstrated to be a more proficient fluorine-transfer reagent than either NFSI or Selectfluor in fluorodecarboxylations of both mono- and difluoroaryloxy acetic acid derivatives. This method efficiently converts a wide range of neutral and electron-poor substrates to afford the desired di- and trifluoromethyl aryl ethers in good to excellent yields. The purifications are facile, and the reaction times are less than 5 min, which makes these fluorodecarboxylations promising for future PET-imaging applications.

Photo-fluorodecarboxylation of 2-aryloxy and 2-aryl carboxylic acids

Coming to light: The title reaction simply requires an aqueous alkaline solution of Selectfluor and light. The method is inexpensive and effective for a wide range of neutral and electron-poor 2-aryloxy and 2-aryl acetic acids to provide fluoromethyl ethers (see scheme) and benzyl fluorides, respectively. The mechanism most likely proceeds through an initial aryl excitation with a subsequent single-electron transfer. Copyright

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CONFORMATIONALLY CONSTRAINED CARBOXYLIC ACID DERIVATIVES USEFUL FOR TREATING METABOLIC DISORDERS

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