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⚫ | | ImageFile = Triethyloxonium tetrafluoroborate.png | ||
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⚫ | | ImageSize = 121 | ||
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| ImageName = Skeletal formula of triethyloxonium tetrafluoroborate | |||
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| ImageFileL1 = Triethyloxonium-3D-balls.png | ||
| ImageFileL1_Ref = {{chemboximage|correct|??}} | |||
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| ImageSizeL1 = 121 | ||
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| ImageNameL1 = Ball and stick model of the triethyloxonium cation | ||
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| ImageFileR1 = Tetrafluoroborate-ion-3D-balls.png | ||
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| ImageFileR1_Ref = {{chemboximage|correct|??}} | |||
| IUPACName = Triethyloxonium tetrafluoroborate | |||
| ImageSizeR1 = 121 | |||
⚫ | | ImageNameR1 = Ball and stick model of the tetrafluoroborate anion | ||
⚫ | | IUPACName = Triethyloxonium tetrafluoroborate | ||
| Section1 = {{Chembox Identifiers | | Section1 = {{Chembox Identifiers | ||
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| CASNo = 368-39-8 | ||
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| PubChem = 2723982 | ||
| PubChem_Ref = {{Pubchemcite|correct|pubchem}} | |||
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| ChemSpiderID = 2006158 | ||
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} | |||
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| UNNumber = 3261 | |||
| Beilstein = 3598090 | |||
| SMILES = F(F)(F)F.CC(CC)CC | |||
| StdInChI = 1S/C6H15O.BF4/c1-4-7(5-2)6-3;2-1(3,4)5/h4-6H2,1-3H3;/q+1;-1 | |||
| StdInChI_Ref = {{stdinchicite|correct|chemspider}} | |||
| StdInChIKey = IYDQMLLDOVRSJJ-UHFFFAOYSA-N | |||
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} | |||
⚫ | }} | ||
| Section2 = {{Chembox Properties | | Section2 = {{Chembox Properties | ||
⚫ | | C = 6 | ||
| Formula = C<sub>6</sub>H<sub>15</sub>BF<sub>4</sub>O | |||
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| H = 15 | ||
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| B = 1 | ||
| F = 4 | |||
| MeltingPt = 91–92 °C | |||
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| O = 1 | ||
| ExactMass = 190.115208388 g mol<sup>-1</sup> | |||
| FlashPt = | |||
| MeltingPtCL = 91 | |||
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| MeltingPtCH = 92 | |||
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| Solubility = Reacts | ||
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⚫ | | Section3 = {{Chembox Hazards | ||
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| EUClass = {{Hazchem C}} | |||
| RPhrases = {{R14}}, {{R34}} | |||
⚫ | | SPhrases = {{S22}}, {{S26}}, {{S36/37/39}} | ||
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Revision as of 08:21, 14 April 2011
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Names | |||
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IUPAC name Triethyloxonium tetrafluoroborate | |||
Identifiers | |||
CAS Number | |||
3D model (JSmol) | |||
Beilstein Reference | 3598090 | ||
ChemSpider | |||
ECHA InfoCard | 100.006.096 | ||
PubChem CID | |||
UN number | 3261 | ||
CompTox Dashboard (EPA) | |||
InChI
| |||
SMILES
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Properties | |||
Chemical formula | C6H15BF4O | ||
Molar mass | 189.99 g·mol | ||
Solubility in water | Reacts | ||
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). Infobox references |
Triethyloxonium tetrafluoroborate is the organic oxonium compound with the formula BF4. It is often called Meerwein's reagent after its discoverer Hans Meerwein. Also well known and commercially available is the related trimethyloxonium tetrafluoroborate. The compounds are exceptionally strong alkylating agents. Aside from the BF4 salt, many related derivatives are available with varying solubilities and stabilities.
Synthesis
Triethyloxonium tetrafluoroborate is prepared from boron trifluoride, diethyl ether, and epichlorohydrin:
- 4 Et2O·BF3 + 2 Et2O + 3 C2H3(O)CH2Cl → 3 Et3OBF4 + B3
The trimethyloxonium salt is available from dimethyl ether via an analogous route. These salts do not have long shelf-lives at room temperature. These salts degrade by hydrolysis:
- BF4 + H2O → (CH3CH2)2O + CH3CH2OH + HBF4
The propensity of trialkyloxoniums to undergo alkyl-exchange may be utilized to the chemists' advantage. For example, trimethyloxonium tetrafluoroborate, which reacts sluggishly due to low solubility in most compatible solvents may be converted in-situ to higher alkyl/more soluble oxoniums, thereby speeding up alkylation reactions.
Structure
The compound features pyramidal oxonium cation and a tetrahedral fluoroborate anion. Reflecting its ionic character, the salt dissolves in polar but inert solvents such as dichloromethane, sulfur dioxide, and nitromethane.
Safety
Triethyloxonium tetrafluoroborate is a strong alkylating agent, although the hazards are diminished because it is non-volatile. It releases strong acid upon contact with water. The properties of the methyl derivative are similar.
Use
Alkylating agent for nucleophilic functional groups in organic synthesis.
References
- H. Meerwein, G. Hinz, P. Hofmann, E. Kroning, and E. Pfeil (1937). "Über Tertiäre Oxoniumsalze, I". Journal für Praktische Chemie. 147 (10–12): 257. doi:10.1002/prac.19371471001.
{{cite journal}}
: CS1 maint: multiple names: authors list (link)H. Meerwein, E. Bettenberg, H. Gold, E. Pfeil, and G. Willfang (1940). "Über Tertiäre Oxoniumsalze, II". Journal für Praktische Chemie. 154 (3–5): 83. doi:10.1002/prac.19391540305.{{cite journal}}
: CS1 maint: multiple names: authors list (link) - Hartwig Perst, Dave G. Seapy "Triethyloxonium Tetrafluoroborate" in Encyclopedia of Reagents for Organic Synthesis John Wiley & Sons, New York, 2008. doi:10.1002/047084289X.rt223.pub2. Article Online Posting Date: March 14, 2008
- H. Meerwein (1973). "Triethyloxonium fluoroborate". Organic Syntheses; Collected Volumes, vol. 5, p. 1080.
- T. J. Curphey (1988). "Trimethyloxonium tetrafluoroborate". Organic Syntheses; Collected Volumes, vol. 6, p. 1019.
- Vartak A.P. and Crooks P.A. (2009). "A Scalable Enantioselective synthesis of the alpha2-adrenergic Agonist, Lofexidine". Org. Process. Res. Dev. 13 (3): 415–419. doi:10.1021/op8002689.
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