tetrafluoroboranuide; triphenylmethanium

• ChemBase ID: 100865
• Molecular Formular: C19H15BF4
• Molecular Mass: 330.1270128
• Monoisotopic Mass: 330.12029376
• SMILES: [B-](F)(F)(F)F.c1c(cccc1)[C+](c1ccccc1)c1ccccc1
• Canonical SMILES: c1ccc(cc1)[C+](c1ccccc1)c1ccccc1.F[B-](F)(F)F
• InChI: InChI=1S/C19H15.BF4/c1-4-10-16(11-5-1)19(17-12-6-2-7-13-17)18-14-8-3-9-15-18;2-1(3,4)5/h1-15H;/q+1;-1
• InChIKey: VQXBOEYKSVVPSP-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: tetrafluoroboranuide; triphenylmethanium; tetrafluoroboranuide; triphenylmethylium
• IUPAC Traditional name: triphenylmethanium tetrafluoroborate; triphenylmethylium tetrafluoroborate
• Synonyms: Tris(phenyl)methylium tetrafluoroborate; Tritylium tetrafluoroborate; Trityl fluoroborate; Tritylium tetrafluoroborate; Triphenylcarbenium tetrafluoroborate; Trityl tetrafluoroborate; 三苯基四氟硼酸碳; 三苯甲基四氟硼酸盐; 三苯甲基四氟硼酸盐; 三苯基四氟硼酸碳

Database IDs

• CAS Number: 341-02-6
• EC Number: 206-433-3
• MDL Number: MFCD00013120
• Beilstein Number: 5085649; 3659536
• PubChem SID: 24850086; 162086656; 24889890
• PubChem CID: 2723955

CALCULATED PROPERTIES

• H Acceptors: 0
• H Donor: 0
• LogD (pH = 5.5): 2.030707
• LogD (pH = 7.4): 2.030707
• Log P: 2.030707
• Molar Refractivity: 79.5869 cm^3
• Polarizability: 31.464106 Å^3
• Polar Surface Area: 0.0 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 205-215 °C (dec.)(lit.); 205-215°C; ca 207°C dec.

Safety Information

• Storage Warning: Corrosive/Moisture Sensitive/Light Sensitive/Keep Cold/Store under Argon; Moisture Sensitive
• European Hazard Symbols: Corrosive (C)
• UN Number: 3261; UN3261
• German water hazard class: 3
• Hazard Class: 8
• Packing Group: 2; II
• Risk Statements: 14-34; 34
• Safety Statements: 26-36/37/39-45
• TSCA Listed: 是
• GHS Pictograms: GHS05
• GHS Signal Word: Danger
• GHS Hazard statements: H314; H314-H318
• GHS Precautionary statements: P280-P303+P361+P353-P305+P351+P338-P310; P280-P305 + P351 + P338-P310
• Personal Protective Equipment: Eyeshields, Faceshields, full-face particle respirator type N100 (US), Gloves, respirator cartridge type N100 (US), type P1 (EN143) respirator filter, type P3 (EN 143) respirator cartridges
• RID/ADR: UN 3261 8/PG 2
• Supplemental Hazard Statements: Reacts violently with water.
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥97.0% (T); 98%
• Grade: purum
• Linear Formula: (C6H5)3C(BF4)

DETAILS

Sigma Aldrich - 164577

Packaging
5, 25 g in poly bottle
Application
Reactant involved in:
• Synthesis of substituted dihydroazulene photoswitches1
• Carbene-based Lewis pairs for hydrogen activation2
• 1,3-Dipolar cycloaddition reactions for preparation of α-amino-β-hydroxy esters3
• Oxidation of allenic compounds4
• Mukaiyama aldol addition reactions 5
• Ionic hydrogenation as a counteranion and ligand source6

Sigma Aldrich - 93457

Other Notes
Reagent for the dehydrogenation of hydroaromatic compounds7; Oxidizing agent8,9; Lewis acid for the reaction of enol silyl ethers with thio acetals10
Application
Reactant involved in:
• Synthesis of substituted dihydroazulene photoswitches1
• Carbene-based Lewis pairs for hydrogen activation2
• 1,3-Dipolar cycloaddition reactions for preparation of α-amino-β-hydroxy esters3
• Oxidation of allenic compounds4
• Mukaiyama aldol addition reactions 5
• Ionic hydrogenation as a counteranion and ligand source6

REFERENCES

• The trityl cation abstracts hydride ion from a variety of substrates:
• Cycloheptatriene gives the tropylium cation: J. Am. Chem. Soc., 79, 4557 (1957).
• With 1,3-Dithiane, A10505, gives the electrophilic dithienium salt which can react with silyl enol ethers to give ɑ-formyl or ɑ-methyl carbonyl compounds: Tetrahedron Lett., 22, 2829, 2833 (1981).
• Abstraction of the ɑ-H atom of alcohols and their O-substituted derivatives results in oxidation to the ketones:
• Oxidation of TMS ethers to ketones: J. Org. Chem., 41, 1479 (1976); secondary alcohols to ketones, and secondary diols to ɑ-hydroxy ketones: Tetrahedron Lett., 2771 (1978). Ketones can similarly be oxidized to ɑ?-unsaturated ketones by hydride abstraction from their silyl enol ethers: J. Org. Chem., 42, 3961 (1977); Synthesis, 736 (1979).
• The trityl cation is also useful for the oxidative cleavage of the 4-methoxybenzyl protecting group from secondary alcohols: J. Org. Chem., 49, 51 (1984).