368-39-8 Usage
Chemical Description
Triethyloxonium tetrafluoroborate is a salt with the formula [(C2H5)3O]BF4.
Description
Triethyloxonium tetrafluoroborate is a white to light yellow crystal powder that serves as a potent alkylating agent, particularly for ethylation. It is widely utilized in various chemical reactions and modifications due to its ability to modify carboxyl residues in proteins and alkylate nucleophilic functional groups in organic synthesis.
Uses
Used in Pharmaceutical and Biochemical Applications:
Triethyloxonium tetrafluoroborate is used as a modifying agent for carboxyl residues in proteins, which is crucial for studying protein structure and function, as well as for the development of new drugs and therapies.
Used in Organic Synthesis:
Triethyloxonium tetrafluoroborate is used as an alkylating agent for nucleophilic functional groups in organic synthesis, enabling the creation of a wide range of chemical compounds with diverse applications.
Used in the Preparation of Amino Esters:
Triethyloxonium tetrafluoroborate is used as a reagent to prepare amino esters by reacting with lactams followed by hydrolysis, which are essential components in the synthesis of various pharmaceuticals and biologically active molecules.
Used in the Synthesis of Substituted Imidazolines:
In the chemical industry, Triethyloxonium tetrafluoroborate is used as a key component in the preparation of substituted imidazolines from aziridines and nitriles via a [3+2]-cycloaddition reaction, which are important intermediates in the synthesis of various organic compounds.
Used in the Synthesis of HDET2:
Triethyloxonium tetrafluoroborate is also utilized in the synthesis of HDET2, a compound with potential applications in various fields, including pharmaceuticals and materials science.
Overall, Triethyloxonium tetrafluoroborate is a versatile and powerful alkylating agent with a wide range of applications in the pharmaceutical, biochemical, and chemical industries, contributing to the development of new drugs, therapies, and synthetic compounds.
Safety Profile
Triethyloxonium tetrafluoroborate is a powerful ethylating agent, although the hazards are diminished because it is non-volatile. It releases strong acid upon contact with water. When heated to decomposition it emits toxic vapors of boronand Fí. Mutation data reported.
Synthesis
Triethyloxonium tetrafluoroborate is prepared from boron trifluoride,diethyl ether and epichlorohydrin:4 Et2O·BF3+ 2 Et2O + 3 C2H3(O)CH2Cl → 3 Et3O+BF4+ B[(OCH(CH2Cl)CH2OEt]3The trimethyloxonium salt is available from dimethyl ether via an analogous route.These salts do not have long shelf-lives at room temperature. They degrade by hydrolysis:[(CH3CH2)3O]+BF4+ H2O → (CH3CH2)2O + CH3CH2OH +HBF4
Purification Methods
Crystallise it from diethyl ether. It is very hygroscopic, and must be handled in a dry box and stored at 0o. [Meerwein Org Synth Coll Vol V 1096 1973.] Pure material should give a clear and colourless solution in dichloromethane (1 in 50, w/v). [Beilstein 1 IV 1322.]
Check Digit Verification of cas no
The CAS Registry Mumber 368-39-8 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 3,6 and 8 respectively; the second part has 2 digits, 3 and 9 respectively.
Calculate Digit Verification of CAS Registry Number 368-39:
(5*3)+(4*6)+(3*8)+(2*3)+(1*9)=78
78 % 10 = 8
So 368-39-8 is a valid CAS Registry Number.
InChI:InChI=1/C6H15O/c1-4-7(5-2)6-3/h4-6H2,1-3H3/q+1
368-39-8Relevant articles and documents
Gluskov,R.G.,Todd,A.R.
, (1968)
Construction of Indole Structure on Pyrroloindolines via AgNTf2-Mediated Amination/Cyclization Cascade: Application to Total Synthesis of (+)-Pestalazine B
Hakamata, Hiroyuki,Ueda, Hirofumi,Tokuyama, Hidetoshi
supporting information, p. 4205 - 4209 (2019/06/17)
An N-linked indole structure was constructed on the 3a-position of pyrroloindoline derivatives via a cascade process involving silver-mediated amination of bromopyrroloindolines with 2-ethynylanilines with subsequent 5-endo-dig cyclization. In this reaction, AgNTf2 was used as a tandem reagent, which activated the bromo group as a σ-Lewis acid and the alkyne moiety as a π-Lewis acid. Switching from the initial step to the second step was conducted by controlling the temperature. This protocol was applied to the synthesis of various pyrroloindolines, α-carboline, and furoindolines and the total synthesis of a dimeric indole alkaloid, (+)-pestalazine B.
NOVEL SUBSTITUTED CONDENSED PYRIMIDINE COMPOUNDS
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Page/Page column 28; 29, (2015/02/25)
Novel substituted condensed pyrimidine compounds of general formula (I) in which the chemical groupings, substituents and indices are as defined in the description, and to their use as medicaments, in particular as medicaments for the treatment of conditions and diseases that can be treated by inhibition of the PDE4 enzyme.
Cysteine prodrugs to treat schizophrenia and drug addiction
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Page/Page column 18-19, (2010/12/29)
The present invention provides cysteine prodrugs for the treatment of schizophrenia and drug addiction. The invention further encompasses pharmaceutical compositions containing prodrugs and methods of using the prodrugs and compositions for treatment of schizophrenia and drug addiction.
