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

Chemical Properties

clear colorless liquid

Originator

Indoklon ,Ohio Medical, US ,1964

Uses

Different sources of media describe the Uses of 333-36-8 differently. You can refer to the following data:
1. 5HT agonist
2. Bis(2,2,2-trifluoroethyl) ether was used to diminish self-discharge of Li-S cells having both low- and high-sulfur-loading sulfur cathodes.
3. Bis(2,2,2-trifluoroethyl) Ether is Prophylactic and/or therapeutic agent for Alzheimer''s disease.

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).

Brand name

Indoklon (Ohmeda).

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 
• 421-83-0 trifluoromethane sulfonyl chloride 
• 501-65-5 diphenyl acetylene 
• 75-88-7 1,1,1-trifluoro-2-chloroethane 
• 6226-25-1 2,2,2-trifluoroethyl trifluoromethanesulphonate 
• 1577195-08-4 [1,8-diazabicyclo(5.4.0)undec-7-ene]⁺[CF₃CH₂OC(O)O]^? 
• 124-38-9 carbon dioxide 
• 407-25-0 trifluoroacetic anhydride 
• 1065-05-0 hexakis(2,2,2-trifluoroethoxy)cyclotriphosphazene 
• 420-87-1 sodium 2,2,2-trifluoroethanolate 
• 353-83-3 1,1,1-trifluoro-2-iodoethane 
• 17178-10-8 2-methoxy-ethyl p-toluenesulfonyloxy ester 
• 109-86-4 2-methoxy-ethanol 
• 433-06-7 2,2,2-Trifluoroethyl p-toluenesulfonate 

Downstream Products

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

Relevant articles and documents

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.

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.