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13826-86-3 - Nitronium tetrafluoroborate, 96% - Nitryl tetrafluoroborate - B20167 - Alfa Aesar

B20167 Nitronium tetrafluoroborate, 96%

CAS-Nummer
13826-86-3
Synonyme
Nitryl tetrafluoroborate

Größe Preis ($) Menge Verfügbarkeit
5g 65,60
25g 192,00
100g 681,00
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Nitronium tetrafluoroborate, 96%

MDL
MFCD00011432
EINECS
237-533-5

Chemische Eigenschaften

Formel
BF4NO2
Molmasse
132.81
Schmelzpunkt
ca 240° dec.
Sensitivität
Moisture Sensitive
Löslichkeit
Decomposes in water.

Anwendungen

Nitronium tetrafluoroborate has been shown to be a versatile nitrating agent for nitrogen compounds, giving the corresponding N-nitro derivative when reacted with secondary aliphatic amines, an acyl aliphatic amine, a carbamate ester: a diacyl amine and primary amides.

Bemerkungen

Moisture sensitive. Store away from oxidizing agents, bases, water/moisture and heat. Keep the container tightly closed and place it in a cool, dry and well ventilated condition. Store under inert gas. Keep it refrigerated.

Literaturverweise

George A. Olah, et al. Aromatic Substitution. VIII.1 Mechanism of the Nitronium Tetrafluoroborate Nitration of Alkylbenzenes in Tetramethylene Sulfone Solution. Remarks on Certain Aspects of Electrophilic Aromatic Substitution2.J. Am. Chem. Soc.,1961,83(22), 4571-4580.

George A. Olah, et al. Electrophilic reactions at single bonds. 25. Nitration of adamantane and diamantane with nitronium tetrafluoroborate.J. Am. Chem. Soc.,1993,115(6), 7246-7249.

Crystalline salt of the active species in the nitration of arenes. Enables nitration to be carried out in non-aqueous, non-acidic systems (typically in Sulfolane, A13466). For mono- and dinitration of o-tolunitrile without hydrolysis, see: J. Chem. Soc., 4257 (1956); J. Am. Chem. Soc., 83, 4564 (1961).

In acetonitrile solution, addition of the nitronium ion to alkenes, followed by Ritter reaction of the resulting carbonium ion with the solvent, leads to the nitroacetamide: J. Org. Chem., 36, 3641 (1971).

Allylsilanes undergo desilylative nitration with allylic rearrangement; in chiral systems the reaction is enantioselective, useful in the synthesis of (E)-olefin dipeptide isosteres: J. Org. Chem., 60, 7714 (1995).

Has also been used for the oxidative cleavage of O-methyl ethers of aliphatic alcohols; e.g. benzyl methyl ether is cleaved to benzaldehyde: J. Org. Chem., 42, 3097 (1977). Ethylene dithioacetals are cleaved to carbonyl compounds: Synthesis, 273 (1979).

GHS Gefahren- und Sicherheitshinweise

Gefahrenhinweise (EU): H314-H318

Causes severe skin burns and eye damage. Causes serious eye damage.

Sicherheitshinweise: P260u-P303+P361+P353-P305+P351+P338-P301+P330+P331-P405-P501a

IF ON SKIN (or hair): Remove/Take off immediately all contaminated clothing. Rinse skin with water/shower. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. IF SWALLOWED: Rinse mouth. Do NOT induce vomiting. Store locked up. Dispose of contents/container in accordance with local/regional/national/international regulations.

Weitere Referenzen

Gefahrenklasse
8
Verpackungsgruppe
II
Harmonized Tariff Code
2826.90
TSCA
Yes
RTECS
QX8620000

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