tetrabutylazanium hydrogen sulfate

• ChemBase ID: 89183
• Molecular Formular: C16H37NO4S
• Molecular Mass: 339.53428
• Monoisotopic Mass: 339.24432967
• SMILES: [N+](CCCC)(CCCC)(CCCC)CCCC.S(=O)(=O)(O)[O-]
• Canonical SMILES: [O-]S(=O)(=O)O.CCCC[N+](CCCC)(CCCC)CCCC
• InChI: InChI=1S/C16H36N.H2O4S/c1-5-9-13-17(14-10-6-2,15-11-7-3)16-12-8-4;1-5(2,3)4/h5-16H2,1-4H3;(H2,1,2,3,4)/q+1;/p-1
• InChIKey: SHFJWMWCIHQNCP-UHFFFAOYSA-M

NAMES AND DATABASE IDS

Names

• IUPAC name: tetrabutylazanium hydrogen sulfate
• IUPAC Traditional name: tetrabutylammonium ion hydrogensulfate; tetrabutylammonium hydrogensulfate
• Synonyms: Hydrogen tetra(but-1-yl)ammonium sulphate 97%; Tetra-n-butylammonium hydrogen sulfate; N,N,N-Tributyl-1-butanaminium Sulfate; Tetrabutyl-ammonium Sulfate; TBAHS-MB; Tetra-n-butylammonium Hydrogen Sulfate; Tetrabutylammonium Hydrosulfate; Tetrabutylammonium Hydrogensulfate; TETRABUTYLAMMONIUM HYDROGEN SULFATE; Tetrabutylammonium hydrogen sulfate; Tetrabutylammonium bisulfate; Tetrabutylammonium hydrogen sulfate solution; Tetrabutylammonium bisulfate solution; Tetrabutylammonium bisulfate solution; Tetrabutylammonium bisulfate, concentrate; Tetrabutylammonium bisulfate; Tetrabutylammonium hydrogensulfate; 正四丁基硫酸氢基铵; 四丁基硫酸氢铵; 四丁基酒石酸氢铵 溶液; 四丁基硫酸氢铵 溶液; Tetrabutylammonium hydrogen sulfate 溶液

Database IDs

• CAS Number: 32503-27-8
• EC Number: 251-068-5
• MDL Number: MFCD00011637
• Beilstein Number: 3599663
• PubChem SID: 162076066; 24886402; 24849572; 24888782; 24888777; 24888793
• PubChem CID: 94433

CALCULATED PROPERTIES

• H Acceptors: 0
• H Donor: 0
• LogD (pH = 5.5): 1.3234289
• LogD (pH = 7.4): 1.3234289
• Log P: 1.3234289
• Molar Refractivity: 91.3961 cm^3
• Polarizability: 31.734425 Å^3
• Polar Surface Area: 0.0 Å^2
• Rotatable Bonds: 12
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; H2O: soluble10 % (w/v), clear, colorless; Methanol
• Apperance: White Solid
• Melting Point: 167-173 °C; 168-172°C; 168-172°C; 169-171 °C(lit.); 169-171°C; 169-173 °C; 171-173°C; 171-174 °C
• Density: 1.01
• Absorption Wavelength: λ: 210 nm Amax: 0.06; λ: 210 nm Amax: 0.10; λ: 220 nm Amax: 0.05; λ: 220 nm Amax: 0.08; λ: 230 nm Amax: 0.03; λ: 230 nm Amax: 0.05; λ: 260 nm Amax: 0.02; λ: 260 nm Amax: 0.05; λ: 500 nm Amax: 0.02

Safety Information

• Storage Condition: Refrigerator; Room Temperature (15-30°C), Desiccate
• Storage Warning: Harmful/Irritant/Hygroscopic/Store under Argon
• European Hazard Symbols: X; Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 22-36/37/38; R:22-36/37/38
• Safety Statements: 26; 26-36; 26-36/37; S:26-36
• TSCA Listed: 是
• GHS Pictograms: GHS06; GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H301-H315-H319-H335; H302-H315-H319-H335; H315-H319
• GHS Precautionary statements: P261-P301+P310-P305+P351+P338-P302+P352-P405-P501A; P261-P305 + P351 + P338; P305 + P351 + P338
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves; Eyeshields, Faceshields, full-face respirator (US), Gloves, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter

Product Information

• Purity: >97%; ≥97.0% (T); ≥99.0%; ≥99.0% (T); 97%
• Concentration: ~55% in H2O
• Grade: for ion pair chromatography; puriss.; purum
• Suitability: corresponds to standard for filter test; corresponds to standard for RP gradient test
• Antion Traces: bromide (Br-): ≤50 mg/kg
• Quality: ampule
• λ: 10 % in H2O; in concentrate
• Linear Formula: (CH3CH2CH2CH2)4N(HSO4)

DETAILS

MP Biomedicals - 02152103

Purity: >97% Crystalline Phase transfer catalyst C16H37NO4S MW 339.5

Sigma Aldrich - 72453

Packaging
250 mL in poly bottle

Sigma Aldrich - 86847

Packaging
concentrate (~0.33 M) in ampules for 6x1L 0.005 M ready-to-use solution

Sigma Aldrich - 155837

Packaging
1 kg in poly bottle
25, 100 g in poly bottle

Toronto Research Chemicals - T289220

Displays antibacterial properties due to the presence of the quaternary amine and the counter ion.

REFERENCES

• Igalsbe, M. L. et al.; Bioorgan. Med. Chem Lett 19, 4984 (2009)
• For phase-transfer catalyzed conversion of nitriles to amides by alkaline H₂O₂, see: Synthesis, 243 (1980).
• In the dehydrohalogenation of aryl 2-haloethyl ethers to give vinyl ethers, this catalyst was found much more effective than the corresponding halides or benzyltriethylammonium salts: Synthesis, 688 (1979).
• The oxidation of primary alcohols to aldehydes by potassium chromate under phase-transfer conditions is better for higher homologues, where solubility in the aqueous phase is limited: Synthesis, 134 (1979). For phase-transfer catalyzed dichromate oxidation of secondary alcohols to ketones, see: Tetrahedron Lett., 1601 (1978).
• For use in the permanganate oxidation of benzylic positions, see Potassium permanganate, A12170.
• Widely used phase-transfer catalyst; see Appendix 2. Some illustrative applications are given below:
• Benzanilides have been N-alkylated in the presence of NaOH and K₂CO₃: Synth. Commun., 18, 2011 (1988).
• It was the most effective catalyst studied for the cyclization of ?-amino acids to ?-lactams by methanesulfonyl chloride and KHCO₃: Chem. Lett., 443 (1981).