Nitronium tetrafluoroborate
| Names | |
|---|---|
| IUPAC name
Nitronium tetrafluoroborate
| |
| Preferred IUPAC name
Nitronium tetrafluoroborate | |
| Other names
Nitronium tetrafluoroborate
Nitryl tetrafluoroborate | |
| Properties | |
| NO2BF4 | |
| Molar mass | 132.81 g/mol |
| Appearance | Colorless crystalline solid |
| Odor | Odorless |
| Density | 1.29 g/cm3 (20 °C) |
| Melting point | 180 °C (356 °F; 453 K) (decomposes) |
| Boiling point | Decomposes |
| Reacts | |
| Solubility | Reacts with acetic acid, dimethylacetamide, dimethylformamide, THF Soluble in acetonitrile, sulfolane Slightly soluble in nitromethane, trifluoroacetic acid |
| Hazards | |
| Safety data sheet | Sigma-Aldrich |
| Flash point | Non-flammable |
| Lethal dose or concentration (LD, LC): | |
| LD50 (Median dose)
|
180 mg/kg (mouse, IV) |
| Related compounds | |
| Related compounds
|
Ammonium tetrafluoroborate |
| Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). | |
| Infobox references | |
Nitronium tetrafluoroborate is an inorganic compound with the chemical formula NO2BF4. It is a salt of nitronium cation and tetrafluoroborate anion.
Contents
Properties
Chemical
Nitronium tetrafluoroborate is used as a nitration agent, replacing the nitrating mixture in many reactions, although due to its poor solubility in many solvents, it's sometimes replaced with the more soluble nitronium hexafluorophosphate.
Nitronium tetrafluoroborate reacts with water.
- NO2BF4 + H2O → HNO3 + HBF4
It also reacts rapidly with acetic anhydride, but less so with acetic acid, dimethylformamide and even slower with acetonitrile, although the reaction is faster at high temperatures. Reaction with acetic acid yields acetyl nitrate. It does not react with sulfolane, which is why it's commonly used as reaction solvent.[1]
NO2BF4 decomposes if heated to 180 °C to NO2F and BF3.[2]
Nitronium tetrafluoroborate oxidizes organic sulfides to sulfoxides. Excess NO2BF4 further oxidizes the sulfoxide to sulfone. Phosphines are similarly oxidized to phosphine oxides.
Physical
Nitronium tetrafluoroborate is a hygroscopic colorless solid.
Availability
Nitronium tetrafluoroborate is sold by chemical suppliers.
Preparation
Nitronium tetrafluoroborate can be prepared by adding a mixture of anhydrous hydrogen fluoride and boron trifluoride to a nitromethane solution of 100% nitric acid or dinitrogen pentoxide. Nitrosonium tetrafluoroborate is also produced as side-product, if the nitric acid used contains traces of nitrogen oxides (such as RFNA).[3]
Projects
- Aromatic nitration
- Make acetyl nitrate
Handling
Safety
Nitronium tetrafluoroborate reacts with water and it's highly corrosive as well as toxic.
Storage
In closed airtight bottles.
Disposal
Should be added slowly to water to safely hydrolyze it, then neutralized with a base.
References
- ↑ Kenneth Schofield, Aromatic Nitration, 1980, p. 88
- ↑ https://onlinelibrary.wiley.com/doi/10.1002/047084289X.rn043
- ↑ https://pubs.acs.org/doi/abs/10.1021/jo00237a043
