66300-61-6

Basic information

• Product Name: 1,4-Di(2,2,2-trifluoroethoxy)benzene
• Synonyms: 1,4-BIS(2,2,2-TRIFLUOROETHOXY)BENZENE;1,4-DI(2,2,2-TRIFLUOROETHOXY)BENZENE;1,4-Bis(2,2,2-trifluoroethoxy)benzene 97%;1,4-Bis(2,2,2-trifluoroethoxy)benzene97%
• CAS NO: 66300-61-6
• Molecular Formula: C₁₀H₈F₆O₂
• Molecular Weight: 274.16
• EINECS: 266-304-2
• Mol File: 66300-61-6.mol
• Article Data: 10

Chemical Properties

• Melting Point: 71-73°C
• Boiling Point: 111-112°C/10mm
• Flash Point: 91.283 °C
• Appearance: /
• Density: 1.349 g/cm³
• Vapor Pressure: 0.208mmHg at 25°C
• Refractive Index: 1.404
• Storage Temp.: Sealed in dry,Room Temperature
• BRN: 4464913
• CAS DataBase Reference: 1,4-Di(2,2,2-trifluoroethoxy)benzene(CAS DataBase Reference)
• NIST Chemistry Reference: 1,4-Di(2,2,2-trifluoroethoxy)benzene(66300-61-6)
• EPA Substance Registry System: 1,4-Di(2,2,2-trifluoroethoxy)benzene(66300-61-6)

Safety Data

• Hazard Codes: Xn
• Statements: 22-36/37/38
• Safety Statements: 22-26-36/37/39
• Hazardous Substances Data: 66300-61-6(Hazardous Substances Data)

Usage

Uses

1,4-Bis(2,2,2-trifluoroethoxy)benzene is useful in ligand design for Cu-Catalyzed Coupling Reactions.

InChI:InChI=1/C10H8F6O2/c11-9(12,13)5-17-7-1-2-8(4-3-7)18-6-10(14,15)16/h1-4H,5-6H2

Upstream product

• 371-67-5 2,2,2-trifluorodiazoethane 
• 123-31-9 hydroquinone 
• 75-89-8 2,2,2-trifluoroethanol 
• 106-37-6 1.4-dibromobenzene 
• 7789-45-9 copper(II)bromide 
• 589-87-7 1,4-bromoiodobenzene 
• 624-38-4 para-diiodobenzene 
• 855719-15-2 trifluoroethanol 
• 76-13-1 1,1,2-Trichloro-1,2,2-trifluoroethane 

Downstream Products

• 66300-56-9 N-[2,5-bis(2,2,2-trifluoroethoxy)phenyl]-N'-[(1-ethylpiperid-2-yl)methyl]urea fumarate 
• 66300-39-8 2,5-bis(2,2,2-trifluoroethoxy)phenyl isocyanate 
• 66300-37-6 2,5-bis(2,2,2-trifluoroethoxy)aniline 
• 66300-35-4 2,5-bis(2,2,2-trifluoroethoxy)nitrobenzene 
• 389082-82-0 2,5-bis(2,2,2-trifluoroethoxy)-α-chloro-acetophenone 

Relevant articles and documents

Synthesis of Fluorinated Alkyl Aryl Ethers by Palladium-Catalyzed C-O Cross-Coupling

Herein, we report a highly effective protocol for the cross-coupling of (hetero)aryl bromides with fluorinated alcohols using the commercially available precatalyst tBuBrettPhos Pd G3 and Cs2CO3 in toluene. This Pd-catalyzed coupling features a short reaction time, excellent functional group tolerance, and compatibility with electron-rich and-poor (hetero)arenes. The method provides access to 18F-labeled trifluoroethyl ethers by cross-coupling with [18F]trifluoroethanol.

Oxalic Diamides and tert-Butoxide: Two Types of Ligands Enabling Practical Access to Alkyl Aryl Ethers via Cu-Catalyzed Coupling Reaction

A robust and practical protocol for preparing alkyl aryl ethers has been developed, which relies on using two types of ligands to promote Cu-catalyzed alkoxylation of (hetero)aryl halides. The reaction scope is very general for a variety of coupling partners, particularly for challenging secondary alcohols and (hetero)aryl chlorides. In case of coupling with aryl chlorides and bromides, two oxalic diamides serve as the powerful ligands. The tert-butoxide is first demonstrated as a ligand for Cu-catalyzed coupling reaction, leading to alkoxylation of aryl iodides complete at room temperature. Additionally, a number of carbohydrate derivatives are applicable for this coupling reaction, affording the corresponding carbohydrate-aryl ethers in 29-98% yields.

Facile access to fluorinated aryl and vinyl ethers through copper-catalysed reaction of fluoro alcohols

Fluorinated alcohols react with aryl and vinyl halides by copper-catalysed cross-coupling reactions to afford the corresponding ethers. With trifluoroethanol (TFE) the reaction proceeds with both iodides and bromides and a wide range of aromatic substituents are tolerated. When higher fluorinated homologues such as C7P15CH2OH were used, the corresponding products were obtained in good yields, thus of-fering an interesting entry to fluorous tagging.