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

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

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

Synthesis of trifluoroethyl ethers from 2,2,2-trifluoroethyl chloride (HCFC-133a) in high temperature aqueous medium

Treatment of 2,2,2-trifluoroethyl chloride (HCFC-133a) with alcohols (phenols) and aqueous KOH in autoclave at 240-280 C gives the corresponding 2,2,2-trifluoroethyl (2-chloro-1,1-difluoroethyl) ethers in good yields.

Synthesis method and application of bis(2, 2, 2-trifluoroethyl) ether

The invention provides a synthesis method of bis(2, 2, 2-trifluoroethyl) ether, which comprises the following steps: preparing 1, 1, 1-trifluorodichloroethane, metering and adding 500-550 parts by weight of ethylene glycol, 0.9-1.1 parts by weight of potassium hydroxide and 100 parts by weight of trifluoroethanol into a pressure reaction kettle, sealing the reaction kettle, introducing 110-130 parts by weight of 1, 1, 1-trifluorodichloroethane, stirring and heating to at least 70-80 DEG C, reacting for 2-4 hours, controlling the temperature of the system to be 70-90 DEG C, adding a polar solvent into the system, uniformly stirring, filtering a potassium chloride solid precipitate to obtain a filtrate, rectifying the filtrate to obtain a product with the purity of 99.98% or above, and providing application of the product as a lithium battery electrolyte solution in the field of lithium batteries. The process has the advantages that raw materials are easy to obtain, supply limitation isavoided, equipment requirements are simple, special material requirements are avoided, the process is simple, production requirements are completely met, clean production is achieved, the equipment cost is reduced, the competitive capacity of company products is improved, and economic benefits are improved.

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.

A trifluoro ethyl ether synthesis method

A trifluoro ethyl ether synthesis method, which belongs to the technical field of synthesis of fluorine-containing ether compound. Characterized in that the preparation steps are: first of all the sodium hydroxide and trifluoro ethanol mixed into a reaction kettle, then adding a dehydrating agent for the synthesis reaction; to obtain sodium alcoholate system, filtering to remove the dehydrating agent, the filtrate collection, the repeated use of the dehydrating agent after drying; the two chlorine asia sulphone drop added to the step 1) sodium alcoholate obtained in the system; the reaction temperature is - 5 °C -20 °C, the reaction time is 1 h - 5 h, then heating up to 20 °C -80 °C continue to reaction 1 h - 5 h; then the reaction system filtering to remove the sodium salt, filtrate distillation trifluoro ethyl ether. The invention solves the technical problems in the preparation of trifluoro ethyl ether: yield is not high, the three waste more in the production process, the production process the higher shortcoming of the risk.

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.

Substituent exchange reactions of trimeric and tetrameric aryloxycyclophosphazenes with sodium 2,2,2-trifluoroethoxide

Substituent exchange reactions of sodium 2,2,2-trifluoroethoxide with trimeric and tetrameric aryloxycyclophosphazenes with phenoxy, 4-formylphenoxy, 4-cyanophenoxy and 4-nitrophenoxy side groups were conducted at 66°C in THF and monitored by 31P NMR and mass spectrometry. These are model reactions for their counterparts with high polymeric linear organophosphazenes. The ease of displacement of OAr in cyclic trimeric and tetrameric molecules by CF3CH2O increased significantly with the presence of electron-withdrawing substituents in the polyphosphazene in the order, phenoxy ? 4-formylphenoxy 4-cyanophenoxy ≈ 4-nitrophenoxy. Fully substituted 2,2,2-trifluoroethoxyphosphazene trimer and tetramer were formed by side group exchange, but these reactions were followed by an attack by the nucleophile on the α-carbon of the 2,2,2-trifluoroethoxy groups linked to phosphorus to give a species in which one trifluoroethoxy group had been replaced by an ONa unit, and bis(trifluoroethyl) ether was formed as a side product. On the other hand, only partly exchanged species were formed when sodium phenoxide reacted with the trifluoroethoxy phosphazene trimer and tetramer, but again a product with an ONa side group was formed eventually together with phenyltrifluoroethyl ether generated via alpha-carbon attack. The relative sensitivity of 2,2,2-trifluoroethoxy and phenoxyphosphazene cyclic trimers and tetramers to the presence of trifluoroethoxide was established.

PROCESS FOR PREPARING FLUORINE-CONTAINING ALKOXYALKANE

A process for preparing a fluorine-containing alkoxyalkane represented by the general formula (1) R1—O—R2—O—R3 where at least one of R1, R2 and R3 contains one or more fluorine atoms. An alcohol with the highest acidity selected from the group consisting of the compounds represented by the general formula (2) R1—OH, the general formula (3) R3—O—R2—OH, the general formula (4) R1—O—R2—OH, and the general formula (5) R3—OH is reacted with at least one selected from the group consisting of the compounds represented by the general formula (6) Lg-R2—O—R3, the general formula (7) Lg-R1, the general formula (8) Lg-R3, and the general formula (9) Lg-R2—O—R1 where Lg represents an anionic leaving group in the presence of a basic compound.

METHOD FOR PRODUCTION OF FLUOROALYKYLFLUOROALKANE-SULFONATE

PROBLEM TO BE SOLVED: To provide a method for simply producing, under more moderate condition than heretofore, a fluoroalkylfluoroalkane-sulfonate useful as an intermediate for medicines or agrochemicals and as a reagent for introducing a fluorine-containing group. SOLUTION: The fluoroalkyl fluoroalkane-sulfonate is produced by reacting a perfluoroalkanesulfonyl halide with a fluorine-containing alcohol in the presence of a base. In this case, an organic solvent is not used but water coexists as a solvent. It is particularly preferable that a reaction temperature is ≥-10°C but ≤40°C and water content is ≥0.2 g and ≤5 g per 1 g of the fluorine-containing alcohol. According to this method, for example, 2,2,2-trifluoroethyltrifluoromethane-sulfonate or 2,2,3,3-tetrafluoropropyltrifluoromethane-sulfonate can efficiently be produced, and the discharge amount of waste materials can remarkably be reduced. COPYRIGHT: (C)2006,JPOandNCIPI

THE THERMOLYTIC DECOMPOSITION OF ACYCLIC PHOSPHORANES

The thermolytic decomposition of acyclic phosphoranes, ArnP(OCH2CF3)5-n in aprotic media has been shown by kinetic studies to proceed via rate-limiting ionization of the phosphoranes.Activation parameters, deuterium isotope effects, solvent effects and ρ-values (for n = 3 and n = 1) support this concept which is consistent with the observed rate-sequence of n = 3> n = 2 > n = 1 > n = 0.Key words: Phosphoranes, thermolysis, kinetics, mechanism.