368-39-8 Usage
Chemical Description
Triethyloxonium tetrafluoroborate is a salt with the formula [(C2H5)3O]BF4.
Chemical Properties
white to light yellow crystal powder.
Uses
Triethyloxonium tetrafluoroborate is used as a powerful alkylating agent, especially for ethylation. It is used for the modification of carboxyl residues in proteins. It is involved in the preparation of μ-amino esters from lactams. It is also alkylating agent for nucleophilic functional groups in organic synthesis.
Application
Triethyloxonium tetrafluoroborate can be used:To prepare amino esters by reacting with lactams followed by hydrolysis.In the preparation of substituted imidazolines from aziridines and nitriles via [3+2]-cycloaddition reaction.For the N-alkylation of a series of N-arylsulfonyl-α-amino acid methyl esters having variable substituents at 4th position of the sulfonamide aromatic ring.Synthesis of HDET2.
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.
