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HomeProduct name listTetrabutylammonium hydrogen sulfate

Tetrabutylammonium hydrogen sulfate

Synonym(s):Tetrabutylammonium bisulfate;Tetrabutylammonium hydrogen sulfate;Tetrabutylammonium hydrogen sulfate solution;Tetra-n-butylammonium hydrogen sulfate

  • CAS NO.:32503-27-8
  • Empirical Formula: C16H37NO4S
  • Molecular Weight: 339.53
  • MDL number: MFCD00011637
  • EINECS: 251-068-5
  • SAFETY DATA SHEET (SDS)
  • Update Date: 2025-02-23 21:28:46
Tetrabutylammonium hydrogen sulfate Structural

What is Tetrabutylammonium hydrogen sulfate?

Chemical properties

It is a stable, hygroscopic, white powder.

The Uses of Tetrabutylammonium hydrogen sulfate

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

The Uses of Tetrabutylammonium hydrogen sulfate

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. Tetrabutylammonium hydrogensulfate is used as a cocatalyst in the synthesis of propionic acid and the ketones by hydrocarboxylation of ethylene. It is also 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.

What are the applications of Application

Tetrabutylammonium bisulfate is a compound that displays antibacterial properties

Preparation

Tetrabutylammonium hydrogen sulfate can be prepared from tetrabutylammonium azide by treating it with potassium hydrogen sulfate and 10% aqueous sulfuric acid in aqueous medium or from tetrabutylammonium thiocyanate by treating it with relatively concentrated sulfuric acid (70%) at 75 °C.


General Description

Tetrabutylammonium hydrogensulfate, a quaternary ammonium salt, is a phase-transfer reagent. It It serves as solvent for the dissolution of ruthenium(II) complex fac-[Ru(CO)2(H2O)3(C(O)C2H5)][CF3SO3]. It participates as a cocatalyst in the reaction medium for the preparation of alternating polyketones and propionic acid.

Purification Methods

The sulfate crystallises from acetone. It has been used as a phase transfer catalyst.

References

[1] H. N. KARADE M. P K M Sathe. An efficient synthesis of 1, 8-dioxo-octahydroxanthenes using tetrabutylammonium hydrogen sulfate[J]. Arkivoc, 2007, 2007 1. DOI:10.3998/ARK.5550190.0008.D28.
[2] A. J. PARDEY. New media in homogeneous catalysis: wet sodium or tetrabutylammonium hydrogensulfate salts for reppe syntheses catalyzed by a ru(ii) carbonyl complex[J]. Journal of Coordination Chemistry, 2004, 57 1: 871-882. DOI:10.1080/00928970410001721998.
[3] A. J. PARDEY. Hydrocarboxylation and stepwise alternating oligomerization of carbon monoxide and ethylene catalyzed by cis-[Rh(CO)2(amine)2](PF6) complexes in a wet liquid tetrabutylammonium hydrogensulfate[J]. Polyhedron, 2004, 23 1: 1677-1683. DOI:10.1016/J.POLY.2004.03.023.
[4] NEETU TEWARI Rama P T Namrata Dwivedi. Tetrabutylammonium hydrogen sulfate catalyzed eco-friendly and efficient synthesis of glycosyl 1,4-dihydropyridines[J]. Tetrahedron Letters, 2004, 45 49: Pages 9011-9014. DOI:10.1016/j.tetlet.2004.10.057.

Properties of Tetrabutylammonium hydrogen sulfate

Melting point: 171-174 °C
Boiling point: 213.3-593.92℃[at 101 325 Pa]
Density  1.01
vapor pressure  0Pa at 25℃
storage temp.  Store below +30°C.
solubility  H2O: soluble10% (w/v), clear, colorless
form  Solution
color  White to beige
Specific Gravity 1.01
PH Range 1 - 2
Odor Amine like
PH 1-2 (100g/l, H2O, 20℃)
Water Solubility  Soluble
Sensitive  Hygroscopic
λmax λ: 210 nm Amax: 0.06
λ: 220 nm Amax: 0.05
λ: 230 nm Amax: 0.03
λ: 260 nm Amax: 0.02
λ: 500 nm Amax: 0.02
BRN  3599663
Stability: Stable, but moisture sensitive. Incompatible with strong oxidizing agents.
CAS DataBase Reference 32503-27-8(CAS DataBase Reference)
NIST Chemistry Reference Tetrabutylammonium hydrogen sulfate(32503-27-8)
EPA Substance Registry System Tetrabutylammonium sulfate (1:1) (32503-27-8)

Safety information for Tetrabutylammonium hydrogen sulfate

Signal word Danger
Pictogram(s)
ghs
Corrosion
Corrosives
GHS05
ghs
Exclamation Mark
Irritant
GHS07
GHS Hazard Statements H302:Acute toxicity,oral
H314:Skin corrosion/irritation
H412:Hazardous to the aquatic environment, long-term hazard
Precautionary Statement Codes P260:Do not breathe dust/fume/gas/mist/vapours/spray.
P273:Avoid release to the environment.
P280:Wear protective gloves/protective clothing/eye protection/face protection.
P301+P312:IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.
P303+P361+P353:IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.
P305+P351+P338:IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

Computed Descriptors for Tetrabutylammonium hydrogen sulfate

InChIKey SHFJWMWCIHQNCP-UHFFFAOYSA-M

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