406-90-6 Usage
Uses
Used in Pharmaceutical Industry:
2,2,2-Trifluoroethyl vinyl ether is used as a precursor for the synthesis of various pharmaceutical compounds due to its unique reactivity and stability. The trifluoromethyl group can enhance the lipophilicity and metabolic stability of the resulting molecules, making them more effective as drugs.
Used in Chemical Synthesis:
In the field of chemical synthesis, 2,2,2-Trifluoroethyl vinyl ether is used as an intermediate for the production of a wide range of fluorinated organic compounds. Its vinyl ether functionality allows for various reactions, such as copolymerization and cross-coupling, to create novel materials with tailored properties.
Used in Material Science:
2,2,2-Trifluoroethyl vinyl ether is used as a monomer in the development of new polymeric materials with enhanced properties, such as improved thermal stability, chemical resistance, and mechanical strength. The incorporation of the trifluoromethyl group into the polymer backbone can significantly alter the material's characteristics.
Used in Anesthesia:
Historically, 2,2,2-Trifluoroethyl vinyl ether was used as an inhalation anesthetic due to its rapid onset and low toxicity. However, it has been largely replaced by more modern anesthetic agents, but it still serves as an important compound in the study of anesthetic mechanisms and the development of new anesthetic drugs.
Originator
Fluoromar, Ohio Medical, US ,1961
Manufacturing Process
The following process description is taken from US Patent 2,830,007.270 grams 2,2,2-trifluoroethanol was added slowly to 15 grams of a cooled suspension of potassium metal in 250 ml of ethyl ether with stirring. When all the potassium metal had reacted, the resulting solution was fractionally distilled in order to remove the ethyl ether. The residue was placed in a bomb and the air was removed from the bomb by flushing with acetylene. The bomb was sealed and heated to 150°C. Acetylene was then introduced at 245 to 260 psi and the gas pressure was maintained for a period of 5 hours under mechanical agitation throughout the reaction. At the end of this time, heating was discontinued, the flow of acetylene was shut off and the bomb was allowed to cool to room temperature. The excess pressure in the bomb was reduced to atmospheric pressure by venting any gases through a dry ice cooled trap.The reaction mixture comprising 2,2,2-trifluoroethyl vinyl ether, 2.2.2trifluoroethanol and potassium 2,2,2-trifluoroethylate was fractionally distilled, whereupon crude 2,2,2-trifluoroethyl vinyl ether was obtained which boiled at 42° to 45°C at 760 mm. More 2,2,2-trifluoroethyl vinyl ether was obtained when the distillation residue was returned to the bomb and reacted with acetylene in the same manner as hereinabove described.The alkali metal hydroxides, instead of the alkali metals per se, can be employed to produce the alkali metal 2,2,2-trifluoroethanolate. However, this introduces water in the reaction mixture which requires removal prior to vinylation with acetylene. The crude products, on further distillation, yielded 2,2,2-trifluoroethyl vinyl ether having a boiling point of 43.1°C at 759 mm.
Reactivity Profile
2,2,2-TRIFLUOROETHYL VINYL ETHER is non-flammable but combustible. Can form explosive mixtures with air. Reacts with strong oxidizing agents.
Safety Profile
Poison by inhalation.
Moderately toxic by intraperitoneal route.
An experimental teratogen. Human systemic
effects by inhalation: jaundice and liver
function tests impaired. Experimental
reproductive effects. Mutation data
reported. When heated to decomposition it
emits toxic fumes of F-. Used as an
anesthetic. See also FLUORIDES and
ETHERS.
Check Digit Verification of cas no
The CAS Registry Mumber 406-90-6 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 4,0 and 6 respectively; the second part has 2 digits, 9 and 0 respectively.
Calculate Digit Verification of CAS Registry Number 406-90:
(5*4)+(4*0)+(3*6)+(2*9)+(1*0)=56
56 % 10 = 6
So 406-90-6 is a valid CAS Registry Number.
InChI:InChI=1/C4H5F3O/c1-2-8-4(6,7)3-5/h2H,1,3H2
406-90-6Relevant academic research and scientific papers
Phosphine-Catalyzed Vinylation at Low Acetylene Pressure
Bienewald, Frank,Comba, Peter,Hashmi, A. Stephen K.,Menche, Maximilian,Rominger, Frank,Schafer, Ansgar,Schaub, Thomas,Sitte, Nikolai A.,Tuzina, Pavel
, p. 13041 - 13055 (2021/09/18)
The vinylation of various nucleophiles with acetylene at a maximum pressure of 1.5 bar is achieved by organocatalysis with easily accessible phosphines like tri-n-butylphosphine. A detailed mechanistic investigation by quantum-chemical and experimental methods supports a nucleophilic activation of acetylene by the phosphine catalyst. At 140 °C and typically 5 mol % catalyst loading, cyclic amides, oxazolidinones, ureas, unsaturated cyclic amines, and alcohols were successfully vinylated. Furthermore, the in situ generation of a vinyl phosphonium species can also be utilized in Wittig-type functionalization of aldehydes.
Preparation method of lansoprazole key intermediate
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Paragraph 0033; 0037; 0041; 0045; 0049; 0053; 0057; 0061, (2020/07/13)
The invention relates to a preparation method of a lansoprazole key intermediate. According to the technical scheme, the preparation method comprises the following steps: firstly, respectively preparing (2, 2, 2-trifluoroethoxy)ethylene (a compound 7) and 3-amino-4-chloro-2-methylbut-2-enoic acid ethyl ester (a compound 9); and then reacting the compound 7 with the compound 9 to prepare 6-(chloromethyl)-5-methyl-4-(2, 2, 2-trifluoroethoxy)-2,3,4,5- tetrahydropyridine; finally, oxidizing 6-(chloromethyl)-5-methyl-4-(2, 2, 2-trifluoroethoxy)-2, 3, 4, 5-tetrahydropyridine (compound 10) by hydrogen peroxide under the catalytic action of Mn(O)-Salon to generate 2-(chloromethyl)-3-methyl-4-(2, 2, 2-trifluoroethoxy)pyridine (compound 5). According to the technical scheme, danger is reduced, energy consumption is reduced, and the method is more suitable for large-scale industrial production.
