333-36-8

Basic information

• Product Name: BIS(2,2,2-TRIFLUOROETHYL) ETHER
• Synonyms: Di(2,2,2-trifluroethyl)ether;Bis(2,2,2-trifluoroethyl) ether 99%;Bis(2,2,2-trifluoroethyl)ether99%;2,2,2-TRIFLUOROETHYL ETHER 99%;2,2,2-Trifluoroethyl ether, Flurothyl;1,1'-Oxybis(2,2,2-trifluoroethane);2,2,2-Trifluoroethyl ether,99%;1,1,1-Trifluoro-2-(2,2,2-trifluoroethoxy)ethane
• CAS NO: 333-36-8
• Molecular Formula: C₄H₄F₆O
• Molecular Weight: 182.06
• Product Categories: IMITREX
• Mol File: 333-36-8.mol
• Article Data: 13

Chemical Properties

• Melting Point: 25°C
• Boiling Point: 62-63 °C(lit.)
• Flash Point: 35 °F
• Appearance: /
• Density: 1.404 g/mL at 25 °C(lit.)
• Vapor Pressure: 180mmHg at 25°C
• Refractive Index: n20/D 1.300(lit.)
• Storage Temp.: Flammables area
• Merck: 14,4201
• BRN: 1811927
• CAS DataBase Reference: BIS(2,2,2-TRIFLUOROETHYL) ETHER(CAS DataBase Reference)
• NIST Chemistry Reference: BIS(2,2,2-TRIFLUOROETHYL) ETHER(333-36-8)
• EPA Substance Registry System: BIS(2,2,2-TRIFLUOROETHYL) ETHER(333-36-8)

Safety Data

• Hazard Codes: F,Xi,T
• Statements: 11-36/37/38
• Safety Statements: 16-26-36
• RIDADR: UN 3271 3/PG 2
• WGK Germany: 3
• RTECS: KN3675000
• HazardClass: 3.1
• PackingGroup: II
• Hazardous Substances Data: 333-36-8(Hazardous Substances Data)

Usage

Description

BIS(2,2,2-TRIFLUOROETHYL) ETHER is a chemical compound with the formula (CF3CH2CH2)2O. It is known for its unique properties, such as its ability to act as a 5HT agonist and its potential use in various applications across different industries.

Uses

Used in Pharmaceutical Industry:
BIS(2,2,2-TRIFLUOROETHYL) ETHER is used as a prophylactic and/or therapeutic agent for Alzheimer's disease. Its potential role in treating this neurodegenerative disorder highlights its importance in the development of new medications for cognitive health.
Used in Energy Storage:
BIS(2,2,2-TRIFLUOROETHYL) ETHER is used as a component to diminish self-discharge of Li-S (Lithium-Sulfur) cells, which have both lowand high-sulfur-loading sulfur cathodes. This application is crucial for improving the performance and longevity of energy storage systems, particularly in electric vehicles and renewable energy applications.
Used in Chemical Research:
BIS(2,2,2-TRIFLUOROETHYL) ETHER is used as a 5HT agonist in chemical research. Its ability to interact with the 5HT (5-hydroxytryptamine) receptors makes it a valuable tool for studying the effects of these receptors on various physiological processes and potential therapeutic applications.

Originator

Indoklon ,Ohio Medical, US ,1964

Manufacturing Process

23 parts of sodium metal were placed in 300 parts of dry dioxane in a reactor equipped with an agitator and reflux condenser. The dioxane was heated to reflux while stirring.150 parts of 2,2,2-trifluoroethanol were added very slowly in the period of about 1 hour, or until the sodium was all reacted, to form sodium 2,2,2-trifluoroethylate. 250 parts of 2,2,2-trifluoroethyl ptoluenesulfonate prepared by reacting 2,2,2-trifluoroethanol with p Flurothyl toluenesulfonyl chloride were placed in another reactor and heated to about 160° to 185°C. The solution of sodium 2,2,2-trifluoroethylate in dioxane was added very slowly over a period of about 1? hours. Bis(2,2,2-trifluoroethyl) ether formed continuously and distilled from the reactor with the dioxane into a cooled receiving vessel. The condensed effluent from the reactor was fractionally distilled, yielding 46.5 parts of products boiling at 55° to 73°C.The crude product was washed successively with concentrated HCl, 62% H2SO4,concentrated H2SO4 and 5% NaOH solution. It was dehydrated over a drying agent and then refractionated in a still. 20 parts of bis(2,2,2trifluoroethyl) ether were recovered (BP 62.5° to 63.5°C).

Therapeutic Function

Central stimulant, Convulsant

InChI:InChI=1/C4H4F6O/c5-3(6,7)1-11-2-4(8,9)10/h1-2H2

Upstream product

• 75-89-8 2,2,2-trifluoroethanol 
• 110-99-6 2,2'-oxybis-acetic acid 
• 421-06-7 2-bromo-1,1,1-trifluoroethane 
• 298-14-6 potassium hydrogencarbonate 
• 75399-87-0 bis(2,2,2-trifluoroethoxy)tri-n-butylphosphorane 
• 371-67-5 2,2,2-trifluorodiazoethane 
• 100-51-6 benzyl alcohol 
• 433-06-7 2,2,2-Trifluoroethyl p-toluenesulfonate 
• 420-87-1 sodium 2,2,2-trifluoroethanolate 
• 75-88-7 1,1,1-trifluoro-2-chloroethane 
• 421-83-0 trifluoromethane sulfonyl chloride 
• 107-21-1 ethylene glycol 
• 109-86-4 2-methoxy-ethanol 
• 353-83-3 1,1,1-trifluoro-2-iodoethane 

Downstream Products

• 119209-26-6 1,1,1,4,4,4-Hexafluoro-2,3-butanediol bis(2,2,2-trifluoroethyl) ether 
• 55605-86-2 1,1,1,2-Tetrafluoro-2-(2,2,2-trifluoro-ethoxy)-ethane 
• 407-38-5 2,2,2-trifluoroethyl trifluoroacetate 
• 32042-38-9 2,2,2-trifluoroethyl formate 

Relevant articles and documents

Breaking the Trend: Insight into Unforeseen Reactivity of Alkynes in Cobalt-Catalyzed Weak Chelation-Assisted Regioselective C(4)-H Functionalization of 3-Pivaloyl Indole

Unique reactivity of diphenylacetylene has been uncovered through weak chelation-assisted cobalt-catalyzed regioselective C(4)-H activation of 3-pivolyl indole. α-Hydroxy ketone and α,β-unsaturated ketone derivatives have been synthesized in good yields from indole and alkynes. Notably, the indole C(4)-H-functionalized α,β-unsaturated ketone product was obtained with high stereo- and regioselectivity simply by changing the coupling partner from symmetrical alkynes to unsymmetrical aromatic-aliphatic alkynes. Most importantly, trifluoroethanol acts as a sole source of water for this conversion. Quantitative detection of bis(2,2,2-trifluoroethyl) ether from dry trifluoroethanol through 19F NMR and LCMS studies indirectly confirms the in situ formation of water. A six-membered cobaltacycle intermediate was detected in HRMS, and also, this was further confirmed by the quantum mechanical calculations, which accounts for the highly regioselective C(4)-H functionalization.

Synthesis of Fluorinated Dialkyl Carbonates from Carbon Dioxide as a Carbonyl Source

Fluorinated dialkyl carbonates (DACs), which serve as environmentally benign phosgene substitutes, were produced successfully from carbon dioxide either directly or indirectly. Nucleophilic addition of 2,2,2-trifluoroethanol to carbon dioxide and subsequent reaction with 2,2,2-trifluoroethyltriflate (3 a) afforded bis(2,2,2-trifluoroethyl) carbonate (1) in up to 79 % yield. Additionally, carbonate 1 was obtained through the stoichiometric reaction of 3 a and cesium carbonate. Although bis(1,1,1,3,3,3-hexafluoro-2-propyl) carbonate (4) was difficult to obtain by either of the above two methods, it could be synthesized through the transesterification of carbonate 1.

Mild partial deoxygenation of esters catalyzed by an oxazolinylborate-coordinated rhodium silylene

An electrophilic, coordinatively unsaturated rhodium complex supported by borate-linked oxazoline, oxazoline-coordinated silylene, and N-heterocyclic carbene donors [{κ3-N,Si,C-PhB(OxMe2)(OxMe2SiHPh)ImMes}Rh(H)CO][HB(C6F5)3] (2, OxMe2 = 4,4-dimethyl-2-oxazoline; ImMes = 1-mesitylimidazole) is synthesized from the neutral rhodium silyl {PhB(OxMe2)2ImMes}RhH(SiH2Ph)CO (1) and B(C6F5)3. The unusual oxazoline-coordinated silylene structure in 2 is proposed to form by rearrangement of an unobserved isomeric cationic rhodium silylene species [{PhB(OxMe2)2ImMes}RhH(SiHPh)CO][HB(C6F5)3] generated by H abstraction. Complex 2 catalyzes reductions of organic carbonyl compounds with silanes to give hydrosilylation products or deoxygenation products. The pathway to these reactions is primarily influenced by the degree of substitution of the organosilane. Reactions with primary silanes give deoxygenation of esters to ethers, amides to amines, and ketones and aldehydes to hydrocarbons, whereas tertiary silanes react to give 1,2-hydrosilylation of the carbonyl functionality. In contrast, the strong Lewis acid B(C6F5)3 catalyzes the complete deoxygenation of carbonyl compounds to hydrocarbons with PhSiH3 as the reducing agent.