368-39-8

Usage

Chemical Description

Triethyloxonium tetrafluoroborate is a salt with the formula [(C2H5)3O]BF4.

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.]

InChI:InChI=1/C6H15O/c1-4-7(5-2)6-3/h4-6H2,1-3H3/q+1

Upstream product

• 74-96-4 ethyl bromide 
• 353-36-6 1-fluoroethane 
• 109-63-7 trifluoroborane diethyl ether 
• 60-29-7 diethyl ether 
• 109-63-7 boron trifluoride diethyl etherate 
• 106-89-8 epichlorohydrin 
• 186581-53-3 diazomethane 
• 21872-75-3 diethoxy(methyl)carbenium tetrafluoroborate 

Downstream Products

• 123-91-1 1,4-dioxane 
• 26448-91-9 4-ethoxy-butyric acid ethyl ester 
• 49619-49-0 3-ethoxy-1H-isoindole 
• 420-37-1 trimethoxonium tetrafluoroborate 
• 74-85-1 ethene 
• 353-36-6 1-fluoroethane 
• 109-63-7 trifluoroborane diethyl ether 
• 999-10-0 ethyl 4-hydroxybutanoate 
• 23994-89-0 2-(ethylthio)-2-thiazoline 
• 18237-66-6 5-ethoxy-3-phenyl-benzo[f][1,4]oxazepine 
• 4156-16-5 2-ethyl-5-phenylisoxazolium-3'-sulphonate 
• 71399-83-2 2-ethylsulfanyl-4-phenyl-3-(toluene-4-sulfonylamino)-thiazolium betaine 

Relevant academic research and scientific papers

Construction of Indole Structure on Pyrroloindolines via AgNTf2-Mediated Amination/Cyclization Cascade: Application to Total Synthesis of (+)-Pestalazine B

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.

A catalytic intramolecular nitrene insertion into a copper(i)-N-heterocyclic carbene bond yielding fused nitrogen heterocycles

N-(2-Azidophenyl)azolium salts were easily prepared and reacted with copper(i) under conditions allowing the formation of NHC complexes. Under these conditions, the formation of benzimidazo-fused heterocycles occurred under catalytic, efficient and very mild conditions. This reaction is proposed to proceed via dinitrogen elimination and imido/nitrene-NHC cyclization.

NOVEL SUBSTITUTED CONDENSED PYRIMIDINE COMPOUNDS

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.

The synthesis and biological testing of bacilysin analogues

A series of compounds based on the structure of bacilysin were synthesised and tested for antibacterial activity. The key steps in the syntheses are the coupling of an iodide to a diketopiperazine (DKP) and mono-lactim ether scaffold, respectively. The diastereoselectivity of the coupling reactions was dependant on the scaffold, with selectivity for DKP of about 4:1 and mono-lactim ether exceeding 98:2. Subsequent elaboration of the compounds to give open chain dipeptides and DKPs that mimic the structure of bacilysin but substitute the epoxy ketone for a saturated or unsaturated ketone is described. Overall yield from coupling to final product was between 5 and 21 %, with the yield of the saturated products notably higher. The open chain dipeptides demonstrated moderate antibacterial and antifungal activity.

Cysteine prodrugs to treat schizophrenia and drug addiction

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.

CYSTEINE AND CYSTINE PRODRUGS TO TREAT SCHIZOPHRENIA AND REDUCE DRUG CRAVINGS

The present invention provides cysteine and cystine 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.

Alternative route to metal halide free ionic liquids

An alternative synthetic route to metal halide free ionic liquids using trialkyloxonium salt is proposed. Utility of this synthetic route has been demonstrated by preparing 1-ethyl-3-methylimidazolium tetrafluoroborate ionic liquid through the reaction be

Cytosporone E: Racemic synthesis and preliminary antibacterial testing

The antibiotic cytosporone E (isolated from the broth of the endophytic fungi CR 200 (Cytospora sp.) and CR 146 (Diaporthe sp.)) was synthesized as a racemic mixture. The key step in the synthesis is the Meyers ortho-alkylation of a chiral aromatic oxazoline. Preliminary antibiotic activity shows antibiosis against Gram-positive bacteria but not Gram-negative bacteria as previously reported.

Method of treating a patient having precancerous lesions with phenyl purinone derivatives

Derivatives of Phenyl Purinone are useful for the treatment of patients having precancerous lesions. These compounds are also useful to inhibit growth of neoplastic cells.

Process for preparing diphenylamines

A process is described for preparing diphenylamines of the formula STR1 by oxybromination of a phenol ether compound using elemental bromine in the presence of hydrogen peroxide and of a catalyst to give a brominated phenol ether compound which is subsequently reacted with a formanilide compound to give the compound of the formula (1). The oxybromination reaction is a regioselective, environmentally friendly and cost-efffective method of preparing brominated aromatic compounds. The diphenylamines of the formula (1) are industrially useful intermediates for the production, for example of dyes, and in particular of color formers of the fluoran type for pressure- or heat-sensitive recording systems.