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A14045 Tropylium tetrafluoroborate, 97%

CAS Number
27081-10-3
Synonyms

Stock No. Size Price ($) Quantity Availability
A14045-06 5g 74.70
A14045-14 25g 200.00
A14045-22 100g 774.00
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Tropylium tetrafluoroborate, 97%

MDL
MFCD00013402
EINECS
248-214-5

Chemical Properties

Formula
C7H7BF4
Formula Weight
177.94
Melting point
ca 240° dec.
Storage & Sensitivity
Keep Cold. Moisture Sensitive.
Solubility
Soluble in hot methanol.

Applications

Reactant or reagent involved in Retro-Buchner reactions for synthesis of arylcyclopropanes, α-Cyanation of imines, electrochemical redox transformations, oxidative C-H activation of aliphatic aldehydes.

Notes

Moisture sensitive. Store under inert gas. Store away from oxidizing agents, strong bases, water/ moisture.

Literature References

Markku Lämsä; Kirsi Raitamaa andJouni Pursiainen. Synthesis of podands bearing aromatic end groups and complex formation with tropylium tetrafluoroborate in 1,2-dichloroethane. Journal of Physical Organic Chemistry. 1999, 12 (7), 557-563.

Stanisław Ostrowski and Mieczysław Mąkosza. Reactions of Organic Anions, 160. Synthesis of Heptafulvene Derivatives by Vicarious Nucleophilic Substitution of Hydrogen in Tropylium Tetrafluoroborate. Environ. Sci. Technol. 1989, 1989 (1), 95-97.

Interesting non-benzenoid aromatic system. For a review of 7-membered conjugated cyclic systems, see: Chem. Rev., 73, 293 (1973).

Reaction with a variety of nucleophiles leads to 7-substituted heptatrienes, e.g. active methylene compounds: Bull. Chem. Soc. Jpn., 50, 3425 (1977); J. Org. Chem., 42, 401 (1977), and organometallic reagents: Bull. Soc. Chim. Fr. 2, 127, 245 (1990).

Undergoes [3+2]-cycloaddition with allenylsilanes, in the presence of a non-nucleophilic acid scavenger, in a general route to azulenes: J. Am. Chem. Soc., 111, 389 (1989):

Propargylsilanes react similarly: J. Org. Chem., 57, 6094 (1992).

For reduction to bitropyl (7,7'-bi-cycloheptatrienyl) by one-electron donating reagents such as low-valent Ti or V, see: Synthesis, 798 (1976).

GHS Hazard and Precautionary Statements

Hazard Statements: H314-H500

Causes severe skin burns and eye damage. May form combustible dust concentrations in air

Precautionary Statements: P260-P264b-P280-P301+P330+P331-P303+P361+P353-P304+P340-P305+P351+P338-P310-P363-P501c

Do not breathe dust/fume/gas/mist/vapours/spray. Wash face, hands and any exposed skin thoroughly after handling Wear protective gloves/protective clothing/eye protection/face protection. IF SWALLOWED: Rinse mouth. Do NOT induce vomiting. IF ON SKIN (or hair): Remove/Take off immediately all contaminated clothing. Rinse skin with water/shower. IF INHALED: Remove to fresh air and keep at rest in a position comfortable for breathing. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. Immediately call a POISON CENTER or doctor/physician. Wash contaminated clothing before reuse. Dispose of contents/ container to an approved waste disposal plant

Other References

Beilstein
3574512
Hazard Class
8
Packing Group
II
Harmonized Tariff Code
2942.00
TSCA
Yes

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