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| | Triethyloxonium tetrafluoroborate Basic information |
| | Triethyloxonium tetrafluoroborate Chemical Properties |
| Melting point | 96-97°C | | density | 1.328 g/mL at 25 °C | | storage temp. | 2-8°C | | solubility | methylene chloride: 20 mg/mL, clear, colorless | | form | Powder | | color | White | | Water Solubility | REACTS | | Sensitive | Moisture Sensitive | | Merck | 14,5796 | | BRN | 3598090 | | Exposure limits | ACGIH: TWA 50 ppm
OSHA: TWA 25 ppm; STEL 125 ppm
NIOSH: IDLH 2300 ppm | | InChI | InChI=1S/C6H15O.BF4/c1-4-7(5-2)6-3;2-1(3,4)5/h4-6H2,1-3H3;/q+1;-1 | | InChIKey | IYDQMLLDOVRSJJ-UHFFFAOYSA-N | | SMILES | [B-](F)(F)(F)F.[O+](CC)(CC)CC | | CAS DataBase Reference | 368-39-8(CAS DataBase Reference) | | EPA Substance Registry System | Oxonium, triethyl-, tetrafluoroborate(1-) (368-39-8) |
| Hazard Codes | C | | Risk Statements | 34-40-14-67-37 | | Safety Statements | 23-24/25-26-36/37/39-45-22 | | RIDADR | UN 3265 8/PG 2 | | WGK Germany | 2 | | RTECS | RR4584700 | | F | 3-10-16-21 | | Hazard Note | Corrosive | | TSCA | Yes | | HazardClass | 4.1 | | PackingGroup | II | | HS Code | 29420000 | | Toxicity | dnd-smc 500 mmol/L CPBTAL 23,2485,75 |
| | Triethyloxonium tetrafluoroborate Usage And Synthesis |
| 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]3
The 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.] |
| | Triethyloxonium tetrafluoroborate Preparation Products And Raw materials |
| Preparation Products | ETHYL ISOCYANIDE-->Ethyl 4-hydroxybutanoate-->(R)-2,5-Dihydro-3,6-diethoxy-2-isopropylpyrazine-->N,N-DIETHYLCYCLOHEXYLAMINE-->1,1-Dibutoxytrimethylamine-->Ethylthiocyanate-->Ethyl nitrate-->2-Bromo-1-ethylpyridinium tetrafluoroborate-->6-ethoxy-2,3,4,5-tetrahydropyridine-->2H-Pyrrole,2-(bromomethyl)-5-ethoxy-3,4-dihydro-,(S)-(9CI)-->2-ethoxyprrole-->2-Ethoxy-1H-indole-->Ethanimidic acid, 2-[[(phenylmethoxy)carbonyl]amino]-, ethyl ester |
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