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)

Safety Information

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

MSDS

• Language:English Provider:Triethyloxonium tetrafluoroborate
• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS
• Language:English Provider:ALFA

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.]

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