352-67-0

Basic information

• Product Name: 4-(Trifluoromethoxy)fluorobenzene
• Synonyms: 4-Fluorophenyl trifluoromethyl ether;Benzene, 1-fluoro-4-(trifluoromethoxy)-;4-FLUORO(TRIFLUOROMETHOXY)BENZENE;4-(TRIFLUOROMETHOXY)FLUOROBENZENE;4-(TRIFLUOROMETHOXY)-1-FLUORBENZENE;1-FLUORO-4-(TRIFLUOROMETHOXY)BENZENE;P-FLUORO(TRIFLUOROMETHOXY)BENZENE;p,alpha,alpha,alpha-tetrafluoroanisole
• CAS NO: 352-67-0
• Molecular Formula: C₇H₄F₄O
• Molecular Weight: 180.1
• EINECS: 206-523-2
• Product Categories: Trifluoroanisole series
• Mol File: 352-67-0.mol
• Article Data: 16

Chemical Properties

• Boiling Point: 104-105 °C(lit.)
• Flash Point: 60 °F
• Appearance: Colorless liquid
• Density: 1.323 g/mL at 25 °C(lit.)
• Vapor Pressure: 35.7mmHg at 25°C
• Refractive Index: n20/D 1.394(lit.)
• Storage Temp.: Room temperature.
• Water Solubility: Not miscible or difficult to mix in water.
• BRN: 2046330
• CAS DataBase Reference: 4-(Trifluoromethoxy)fluorobenzene(CAS DataBase Reference)
• NIST Chemistry Reference: 4-(Trifluoromethoxy)fluorobenzene(352-67-0)
• EPA Substance Registry System: 4-(Trifluoromethoxy)fluorobenzene(352-67-0)

Safety Data

• Hazard Codes: F,Xi
• Statements: 11-36/37/38
• Safety Statements: 16-26-36/37/39
• RIDADR: UN 1993 3/PG 2
• WGK Germany: 3
• HazardClass: 3
• PackingGroup: II
• Hazardous Substances Data: 352-67-0(Hazardous Substances Data)

Usage

InChI:InChI=1/C7H4F4O/c8-5-1-3-6(4-2-5)12-7(9,10)11/h1-4H

Upstream product

• 407-13-6 (4-fluoro-phenyl)-trichloromethyl ether 
• 658-75-3 p-fluorophenyl trifluoroacetate 
• 459-60-9 1-fluoro-4-methoxybenzene 
• 3582-05-6 trifluoromethyl trifluoromethanesulfonate 
• 17151-47-2 tributyl(4-fluorophenyl)stannane 
• 1765-93-1 4-fluoroboronic acid 
• 96898-10-1 tris(dimethylamino)sulfonium trifluoromethoxide 
• 1394827-04-3 potassium (4-(trifluoromethoxy)phenyl)trifluoroborate 
• 338792-64-6 α,α-difluoro(4-fluorophenoxy)acetic acid 
• 807368-70-3 ethyl 2-(4-fluorophenoxy)-2,2-difluoroacetate 
• 371-41-5 4-Fluorophenol 
• 462-06-6 fluorobenzene 
• 2070902-77-9 trifluoromethyl 4-fluorobenzene-1-sulfonate 
• 371-40-4 4-fluoroaniline 

Downstream Products

• 123572-62-3 4-fluoro-2-nitro-1-trifluoromethoxy-benzene 
• 124170-06-5 1-fluoro-2-nitro-4-(trifluoromethoxy)benzene 
• 287952-66-3 tert-butyl 4-(4-(trifluoromethoxy)phenoxy)piperidin-1-carboxylate 
• 74030-45-8 4-(4-(trifluoromethoxy)phenoxy)phenol 
• 123572-63-4 5-fluoro-2-trifluoromethoxy-phenylamine 
• 182289-59-4 4-Chloro-1-methyl-5-methylsulfanyl-3-(4-trifluoromethoxy-phenoxy)-1H-pyrazole 
• 182289-80-1 N-[5-(4-Chloro-1-methyl-5-methylsulfanyl-1H-pyrazol-3-yloxy)-2-trifluoromethoxy-phenyl]-acetamide 
• 886497-81-0 2-fluoro-5-(trifluoromethoxy)benzaldehyde 
• 1268051-89-3 (5-fluoro-2-trifluoromethoxyphenyl)carbamic acid ethyl ester 
• 116369-23-4 2-fluoro-5-(trifluoromethoxy)aniline 
• 1268051-91-7 (3-fluoro-2-iodo-6-trifluoromethoxyphenyl)carbamic acid ethyl ester 

Relevant articles and documents

Radical C?H Trifluoromethoxylation of (Hetero)arenes with Bis(trifluoromethyl)peroxide

Trifluoromethoxylated (hetero)arenes are of great interest for several disciplines, especially in agro- and medicinal chemistry. Radical C?H trifluoromethoxylation of (hetero)arenes represents an attractive approach to prepare such compounds, but the high cost and low atom economy of existing .OCF3 radical sources make them unsuitable for the large-scale synthesis of trifluoromethoxylated building blocks. Herein, we introduce bis(trifluoromethyl)peroxide (BTMP, CF3OOCF3) as a practical and efficient trifluoromethoxylating reagent that is easily accessible from inexpensive bulk chemicals. Using either visible light photoredox or TEMPO catalysis, trifluoromethoxylated arenes could be prepared in good yields under mild conditions directly from unactivated aromatics. Moreover, TEMPO catalysis allowed for the one-step synthesis of valuable pyridine derivatives, which have been previously prepared via multi-step approaches.

Visible-Light Photoredox-Catalyzed and Copper-Promoted Trifluoromethoxylation of Arenediazonium Tetrafluoroborates

We report the development of photoredox-catalyzed and copper-promoted trifluoromethoxylation of arenediazonium tetrafluoroborates, with trifluoromethyl arylsulfonate (TFMS) as the trifluoromethoxylation reagent. This new method takes advantage of visible-light photoredox catalysis to generate the aryl radical under mild conditions, combined with copper-promoted selective trifluoromethoxylation. The reaction is scalable, tolerates a wide range of functional groups, and proceeds regioselectively under mild reaction conditions. Furthermore, mechanistic studies suggested that a Cs[Cu(OCF3)2] intermediate might be generated during the reaction.

Silver-Mediated Trifluoromethoxylation of (Hetero)aryldiazonium Tetrafluoroborates

Here we report a silver-mediated trifluoromethoxylation of (hetero)aryldiazonium tetrafluoroborates by converting an aromatic amino group into an OCF3 group. This method, which can be considered to be a trifluoromethoxylation variation of the classic Sandmeyer-type reaction, uses readily available aryl and heteroaromatic amines as starting materials and AgOCF3 as trifluoromethoxylating reagents. The broad substrate scope and simple, mild reaction condition made this transformation a valuable method in constructing aryl-OCF3 bonds.