tetrafluoroboranuide; triethyloxidanium

• ChemBase ID: 99456
• Molecular Formular: C6H15BF4O
• Molecular Mass: 189.9873128
• Monoisotopic Mass: 190.11520838
• SMILES: [O+](CC)(CC)CC.[B-](F)(F)(F)F
• Canonical SMILES: F[B-](F)(F)F.CC[O+](CC)CC
• InChI: InChI=1S/C6H15O.BF4/c1-4-7(5-2)6-3;2-1(3,4)5/h4-6H2,1-3H3;/q+1;-1
• InChIKey: IYDQMLLDOVRSJJ-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: tetrafluoroboranuide; triethyloxidanium
• IUPAC Traditional name: triethyloxidanium tetrafluoroborate
• Synonyms: Triethyloxonium tetrafluoroborate 95%; Triethyloxonium tetraflouroborate; MEERWEIN'S REAGENT; Triethyloxonium tetrafluoroborate, 1.0M in dichloromethane; Triethyloxonium tetrafluoroborate; Triethyloxonium tetrafluoroborate solution; Triethyloxonium tetrafluoroborate; Triethyloxonium tetrafluoroborate, 1.0 M in dichloromethane; 三乙基氧鎓四氟硼酸盐, 1.0M 二氯甲烷溶液; 三乙基氧鎓四氟硼酸盐 溶液; 三乙基氧鎓四氟硼酸盐; 三乙基氧鎓四氟硼酸盐, 1.0M二氯甲烷溶液, 氩气下可重封的ChemSeal™瓶包装

Database IDs

• CAS Number: 368-39-8
• EC Number: 206-705-1
• MDL Number: MFCD00044423
• Beilstein Number: 3598090
• PubChem SID: 24850566; 24889378; 162085721; 24889377
• PubChem CID: 2723982
• Chemspider ID: 2006158
• Wikipedia Title: Triethyloxonium_tetrafluoroborate

CALCULATED PROPERTIES

• H Acceptors: 1
• H Donor: 0
• LogD (pH = 5.5): 0.589
• LogD (pH = 7.4): 0.589
• Log P: 0.589
• Molar Refractivity: 44.4508 cm^3
• Polarizability: 14.022011 Å^3
• Polar Surface Area: 13.59 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: methylene chloride: soluble20 mg/mL, clear, colorless; Reacts in water
• Apperance: Liquid
• Melting Point: 84-89°C; 84-89°C; 91 - 92°C
• Density: 1.305 g/mL at 20 °C; 1.328; 1.328 g/mL at 25 °C

Safety Information

• Storage Condition: Room Temperature (15-30°C)
• Storage Warning: Highly Flammable/Corrosive/Moisture Sensitive/Keep Cold/Store under Argon; Moisture Sensitive
• RTECS: RR4584700
• European Hazard Symbols: Corrosive (C); Flammable (F); X
• UN Number: 3261; 3265; UN2922; UN2925
• German water hazard class: 3
• Hazard Class: 4.1; 8
• Packing Group: 2; II
• Risk Statements: 11-34; 14-34; 14-34-40; 34-40; R14, R34
• Safety Statements: 16-26-36/37/39-45; 23-26-36/37/39-45; 26-36/37/39-45; S22, S26, S36/37/39
• TSCA Listed: 是
• GHS Pictograms: GHS02; GHS05; GHS08
• GHS Signal Word: Danger
• GHS Hazard statements: H228-H314-H318; H314; H314-H318-H351; H314-H351
• GHS Precautionary statements: P210-P280-P303+P361+P353-P305+P351+P338-P310; P260-P303+P361+P353-P305+P351+P338-P301+P330+P331-P405-P501A; P261-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; Faceshields, full-face respirator (US), Gloves, Goggles, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter
• RID/ADR: UN 3261 8/PG 2; UN 3265 8/PG 2
• Supplemental Hazard Statements: Reacts violently with water.
• Storage Temperature: -20°C; 2-8°C

Product Information

• Purity: ≥97.0% (T); 95%, stab. with 3-5% diethyl ether
• Concentration: ~1 M in methylene chloride; 1.0 M in methylene chloride; 1.0M in dichloromethane
• Grade: purum
• Packaging: packaged under Argon in resealable ChemSeal? bottles
• Contains: 1-3% ether as stabilizer
• Linear Formula: (C2H5)3O(BF4)

DETAILS

Apollo Scientific Ltd - PC7110

Powerful alkylating reagent for many reactions. Stabilised with diethyl ether

Sigma Aldrich - 176230

Packaging
100 mL in Sure/Seal™
Application
Used in the preparation of ω-aminoesters from lactams.1

Sigma Aldrich - 90520

Other Notes
Powerful ethylating agent1,2; Esterification of acids3; Modifies carboxyl residues in proteins4,5
Packaging
25, 100 g in glass bottle

REFERENCES

• Trialkyloxonium salts, also known as Meerwein's salts, are powerful alkylating agents: Chem. Ber., 89, 209, 2060 (1956). For a brief feature on uses of Meerwein's salts in synthesis, see: Synlett, 195 (2004).
• In combination with a hindered base, e.g. N-Ethyldiisopropylamine, A11801, is a convenient reagent for the conversion of carboxylic acids to their ethyl esters by O-alkylation: Tetrahedron Lett., 4741 (1971); Org. Synth. Coll., 6, 576 (1988).
• Secondary and tertiary amides are O-alkylated to give immonium salts and imino ethers, respectively. Reduction with borohydride provides an effective amide to amine conversion: Tetrahedron Lett., 61 (1968):
  
• Likewise, N-alkylation of nitriles results in their activation to reduction by triethylsilane to give aldehydes, via the imines: Synthesis, 420 (1973); J. Chem. Soc., Chem. Commun., 45 (1974); J. Org. Chem., 46, 602 (1981).
• For further reactions of trialkyloxonium salts, see Trimethyloxonium tetrafluoroborate, A15175.