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A14047 Tetra-n-butylammonium hydrogen sulfate, 97%

CAS Number
32503-27-8
Synonyms

Stock No. Size Price ($) Quantity Availability
A14047-18 50g 45.30
A14047-30 250g 141.00
A14047-0B 1000g 304.00
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Tetra-n-butylammonium hydrogen sulfate, 97%

MDL
MFCD00011637
EINECS
251-068-5

Chemical Properties

Formula
[CH3(CH2)3]4NHSO4
Formula Weight
339.54
Melting point
168-172°
Storage & Sensitivity
Hygroscopic. Ambient temperatures.
Solubility
Soluble in water.

Applications

Phase transfer catalyst Tetra-n-butylammonium hydrogen sulfate shows antibacterial properties due to the presence of the quaternary amine and the counter ion. It serves as a phase-transfer catalyst, surface-active agent, solvent, intermediate, active ingredient for conditioners, antistatic agent, detergent sanitizers, softener for textiles and paper products, emulsifying agents and pigment dispersers. It is used as an efficient catalyst in the N-alkylation reactions of benzanilides, cyclization of beta-amino acids to beta-lactams, conversion of nitriles to amides, dehydrohalogenation of aryl 2-haloethyl ethers to give vinyl ethers and in the oxidation of alcohols.

Notes

Moisture sensitive. Keep the container tightly closed in a dry and well-ventilated place. Incompatible with strong oxidizing agents.

Literature References

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 ß-amino acids to ß-lactams by methanesulfonyl chloride and KHCO3: Chem. Lett., 443 (1981).

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).

For use in the permanganate oxidation of benzylic positions, see Potassium permanganate, A12170.

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 phase-transfer catalyzed conversion of nitriles to amides by alkaline H2O2, see: Synthesis, 243 (1980).

Pandian, T. S.; Choi, Y.; Srinivasadesikan, V.; Lin, M. C.; Kang, J. A dihydrogen phosphate selective anion receptor based on acylhydrazone and pyrazole. New J. Chem. 2015, 39 (1), 650-658.

Taguchi, H.; Yanagisawa, D.; Morikawa, S.; Hirao, K.; Shirai, N.; Tooyama, I. Synthesis and Tautomerism of Curcumin Derivatives and Related Compounds. Aust. J. Chem. 2015, 68 (2), 224-229.

GHS Hazard and Precautionary Statements

Hazard Statements: H302-H315-H319-H335

Harmful if swallowed. Causes skin irritation. Causes serious eye irritation. May cause respiratory irritation.

Precautionary Statements: P261-P264b-P270-P271-P280-P301+P312-P302+P352-P304+P340-P305+P351+P338-P312-P330-P332+P313-P337+P313-P362-P501c

Avoid breathing dust/fume/gas/mist/vapours/spray. Wash face, hands and any exposed skin thoroughly after handling Do not eat, drink or smoke when using this product. Use only outdoors or in a well-ventilated area. Wear protective gloves/protective clothing/eye protection/face protection. IF SWALLOWED: Call a POISON CENTER or doctor/physician if you feel unwell. IF ON SKIN: Wash with plenty of soap and water. 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. Rinse mouth. If skin irritation occurs: Get medical advice/attention. If eye irritation persists: Take off contaminated clothing and wash before reuse. Dispose of contents/ container to an approved waste disposal plant

Other References

Harmonized Tariff Code
2923.90
TSCA
Yes

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