cyclohepta-2,4,6-trien-1-ylium; tetrafluoroboranuide

• ChemBase ID: 10324
• Molecular Formular: C7H7BF4
• Molecular Mass: 177.9350928
• Monoisotopic Mass: 178.0576935
• SMILES: [B-](F)(F)(F)F.C1=CC=C[CH+]C=C1
• Canonical SMILES: C1=C[CH+]C=CC=C1.F[B-](F)(F)F
• InChI: InChI=1S/C7H7.BF4/c1-2-4-6-7-5-3-1;2-1(3,4)5/h1-7H;/q+1;-1
• InChIKey: SQVQHTIKOZVGLR-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: cyclohepta-2,4,6-trien-1-ylium; tetrafluoroboranuide
• IUPAC Traditional name: tropylium tetrafluoroborate
• Synonyms: Tropylium tetrafluoroborate; Cyclohepta-2,4,6-trienylium tetrafluoroborate 95%; Tropylium tetrafluoroborate; Tropylium tetrafluoroborate; 四氟硼酸卓鎓

Database IDs

• CAS Number: 27081-10-3
• EC Number: 248-214-5
• MDL Number: MFCD00013402
• Beilstein Number: 3574512
• PubChem SID: 160973631
• PubChem CID: 152926
• Chemspider ID: 134784
• Wikipedia Title: Tropylium_tetrafluoroborate

CALCULATED PROPERTIES

• H Acceptors: 0
• H Donor: 0
• LogD (pH = 5.5): -1.1260408
• LogD (pH = 7.4): -1.1260408
• Log P: -1.1260408
• Molar Refractivity: 30.401 cm^3
• Polarizability: 12.014511 Å^3
• Polar Surface Area: 0.0 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 240°C; ca 240°C(dec); ca 240°C dec.

Safety Information

• Storage Warning: IRRITANT, MOISTURE SENSITIVE, KEEP COLD; Irritant/Keep Cold/Moisture Sensitive; Moisture Sensitive
• European Hazard Symbols: Corrosive (C)
• UN Number: UN1759
• Hazard Class: 8
• Packing Group: III
• Risk Statements: 34
• Safety Statements: 20-26-36/37/39-45-60
• TSCA Listed: false; 是
• GHS Pictograms: GHS05
• GHS Hazard statements: H314-H318
• GHS Precautionary statements: P260-P303+P361+P353-P305+P351+P338-P301+P330+P331-P405-P501A

Product Information

• Purity: 95%; 97%

REFERENCES

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