Nitronium tetrafluoroborate

Structural formula
General
Surname	Nitronium tetrafluoroborate
Molecular formula	NO 2 [BF 4 ]
Brief description	colorless solid
External identifiers / databases
CAS number 13826-86-3 EC number 237-533-5 ECHA InfoCard 100.034.107 PubChem 11073463 ChemSpider 9248612 Wikidata Q424900
properties
Molar mass	132.81 g · mol -1
Physical state	firmly
Melting point	240 ° C (decomposition)
solubility	Decomposes in water
safety instructions
GHS labeling of hazardous substances danger H and P phrases H: 314-317-334 P: 261-280-305 + 351 + 338-310
MAK	2.5 mg m −3
As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Nitronium tetrafluoroborate is a chemical compound . It is the tetrafluoroborate - salt of the nitronium ion .

presentation

The salt can be made by reacting anhydrous hydrofluoric acid with boron trifluoride and nitrous pentoxide in nitromethane .

use

Nitronium tetrafluoroborate is used as a reactive reagent for the nitration of aromatics . Nitrations run better with this salt and under milder conditions than with the conventional nitration protocol, in which nitronium ions are produced in situ from nitric acid and sulfuric acid. It nitrates benzene to nitrobenzene and even 2,6-dibromopyridine .

Individual evidence

1. ↑ ^{a b c d} data sheet nitronium tetrafluoroborate from AlfaAesar, accessed on March 2, 2010 ( PDF )(JavaScript required) .
2. ↑ ^{a b} data sheet Nitronium tetrafluoroborate from Sigma-Aldrich , accessed on April 16, 2011 ( PDF ).
3. ↑ K. Schofield: Aromatic nitration. 1st edition. Cambridge University Press, Cambridge, ISBN 0-521-23362-3 , p. 88.
4. ↑ J. Buddrus: Fundamentals of organic chemistry. 3. Edition. de Gruyter Verlag, 2003, ISBN 3-11-014683-5 , p. 344.
5. ↑ JL Duffy, KK Laali: Aprotic Nitration (NO ₂ ⁺ BF ₄ ^- ) of 2-Halo- and 2,6-Dihalopyridines and Transfer-Nitration Chemistry of Their N-Nitropyridinium Cations. In: J. Org. Chem. 1991, 56, pp. 3006-3009. doi : 10.1021 / jo00009a015