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14635-75-7 - Nitrosonium tetrafluoroborate, 98% - Nitrosyl tetrafluoroborate - A15806 - Alfa Aesar

A15806 Nitrosonium tetrafluoroborate, 98%

Codice CAS
14635-75-7
Sinonimi
Nitrosyl tetrafluoroborate

Dimensioni Prezzo ($) Quantità Disponibilità
2g 29,75
10g 72,10
50g 285,31
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Nitrosonium tetrafluoroborate, 98%

MDL
MFCD00011433
EINECS
238-679-2

Proprietà chimiche

Formula
NOBF4
Peso formula
116.82
Punto di fusione
250° subl.
Punto di ebollizione
250°/0.01mm subl.
Densità
2.185
Sensibilità
Moisture Sensitive
Solubilità
Soluble in acetonitrile.

Applicazioni

Nitrosonium tetrafluoroborate is a nitrosating agent and oxidizer used in organic synthesis. It is also used to convert arylamines directly to diazonium tetrafluoroborates, which undergo the Balz-Schiemann reaction in situ to give high yields of aryl fluorides. Further, it is used as a catalyst for iodination of aromatics by iodide ion with air as oxidant, conversion of secondary amines to nitrosamines and in deamination of primary amides. It is involved in the conversion of arylhydrazines to azides. In addition to this, it reacts with ferrocene to prepare ferrocenium tetrafluoroborate.

Note

Hygroscopic. Air and moisture sensitive. Store in a cool place. Keep the container tightly closed in a dry and well-ventilated place. Incompatible with acids and amines.

Letteratura

Crystalline nitrosating agent: Secondary amines to nitrosamines: Chem. Ber., 89, 2374 (1956); deamination of primary amides: J. Org. Chem., 30, 2386 (1965); conversion of arylhydrazines to azides: Tetrahedron Lett., 28, 5091 (1987). In organic solvents, converts arylamines directly to diazonium tetrafluoroborates which undergo the Balz-Schiemann reaction (see Tetrafluoroboric acid, L14037 ) in situ to give high yields of aryl fluorides: Chem. Ber., 88, 1939 (1955); EP 430,434 (1991). Methyl or methoxy substituted aromatics in acetonitrile give the nitrosoaromatics in good yield: J. Org. Chem., 59, 5573 (1994).

Convenient catalyst for iodination of aromatics by iodide ion with air as oxidant: J. Org. Chem., 53, 3548 (1988), or for addition of iodine (or iodine + nucleophile) to alkenes: Acta Chem. Scand. B, 43, 902 (1989).

Undergoes an interesting insertion reaction with diarylcyclopropanes: Chem. Lett., 233 (1988):

With excess reagent, oxidation of the isoxazoline to the isoxazole occurs.

Yang, Y.; Yao, Y.; He, L.; Zhong, Y.; Ma, Y.; Yao, J. Nonaqueous synthesis of TiO2-carbon hybrid nanomaterials with enhanced stable photocatalytic hydrogen production activity. J. Mater. Chem. A 2015, 3 (18), 10060-10068.

Bandi, V.; Gobeze, H. B.; Lakshmi, V.; Ravikanth, M.; D’Souza, F. Vectorial Charge Separation and Selective Triplet-State Formation during Charge Recombination in a Pyrrolyl-Bridged BODIPY-Fullerene Dyad. J. Phys. Chem. C 2015, 119 (15), 8095-8102.

Rischio GHS e dichiarazioni precauzionali

Dichiarazioni di rischio (UE): H314-H318

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

Dichiarazioni precauzionali: P260-P280-P303+P361+P353-P305+P351+P338-P301+P330+P331-P304+P340-P310-P363-P405-P501a

Do not breathe dust/fume/gas/mist/vapours/spray. Wear protective gloves/protective clothing/eye protection/face protection. 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. IF INHALED: Remove to fresh air and keep at rest in a position comfortable for breathing. Immediately call a POISON CENTER or doctor/physician. Wash contaminated clothing before reuse. Store locked up. Dispose of contents/container in accordance with local/regional/national/international regulations.

Altri riferimenti

Merck
14,6649
Classe di rischio
8
Gruppo di imballaggio
II
Codice tariffe armonizzato
2812.90
TSCA
Yes

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