Product Introduction
| Tetrabutylammonium hydrogen sulfate Basic information |
| Product Name: | Tetrabutylammonium hydrogen sulfate |
| Synonyms: | ammonium hydrog;en suL;fate;Tetrabutylammonium Hydrogen Sulfate [Reagent for Ion-Pair Chromatography];TETRA-N-BUTYLAMMONIUM HYDROGENSULFATE;TETRA-N-BUTYLAMMONIUM HYDROGEN SULPHATE;TETRABUTYLAMMONIUM HYDROGEN SULFATE;TETRABUTYLAMMONIUM HYDROGEN SULPHATE |
| CAS: | 32503-27-8 |
| MF: | C16H37NO4S |
| MW: | 339.53 |
| EINECS: | 251-068-5 |
| Product Categories: | Ion-pair Reagents;Ammonium Polyhalides, etc. (Quaternary);Analytical Chemistry;HPLC Ion-Pair Reagents for Acidic Samples;Ion-Pair Reagents for HPLC;Quaternary Ammonium Compounds;quarternary ammonium salts;Miscellaneous Reagents;Pharmaceutical intermediates;32503-27-8;bc0001 |
| Mol File: | 32503-27-8.mol |
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| Tetrabutylammonium hydrogen sulfate Chemical Properties |
| 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 | 1-2 (100g/l, H2O, 20℃) |
| Odor | Amine like |
| PH Range | 1 - 2 |
| 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. |
| InChIKey | SHFJWMWCIHQNCP-UHFFFAOYSA-M |
| LogP | 0.96 at 25℃ |
| 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 |
| Hazard Codes | Xn,Xi |
| Risk Statements | 36/37/38-22 |
| Safety Statements | 26-36-37/39 |
| WGK Germany | 3 |
| F | 8-10 |
| Hazard Note | Irritant |
| TSCA | Yes |
| HS Code | 29239000 |
| MSDS Information |
| Provider | Language |
|---|---|
| TBAHS | English |
| SigmaAldrich | English |
| ACROS | English |
| ALFA | English |
| Tetrabutylammonium hydrogen sulfate Usage And Synthesis |
| Chemical Properties | It is a stable, hygroscopic, white powder. |
| Uses | A compound that displays antibacterial properties due to the presence of the quaternary amine and the counter ion. Tetrabutylammonium hydrogen sulfate is an ion pairing reagent that is used in liquid chromatography. It is frequently utilized in the analysis of pharmaceutical compounds and metabolites. |
| Uses | 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. |
| 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. |
| Tetrabutylammonium hydrogen sulfate Preparation Products And Raw materials |
| Raw materials | Tributylamine-->1-Iodobutane-->Potassium pyrosulfate |
| Preparation Products | 3-AMINO-2,2-DIMETHYL-4-OXO-AZETIDINE-1-SULFONIC ACID-->Hydroxytyrosol-->1-Bromo-4-methoxybutane-->4-(2-(PIPERIDIN-1-YL)ETHOXY)-3,5-DICHLOROBENZENAMINE-->1-(3-(4-AMINO-2,6-DICHLOROPHENOXY)PROPYL)PYRROLIDIN-2-ONE-->Tetrabutylammonium azide-->1-(4-AMINO-2,6-DICHLOROPHENOXY)-3-(PYRROLIDIN-1-YL)PROPAN-2-OL-->(S)-(+)-5-(Hydroxymethyl)-2-pyrrolidinone p-toluenesulfonate-->Bis(tetrabutylammonium) sulphate-->4,6-DIMETHYL-PYRIMIDINE-2-SULFONYL FLUORIDE-->4-Biphenylacetonitrile-->5-METHYL-PYRIMIDINE-2-SULFONYL FLUORIDE-->4-METHYL-PYRIMIDINE-2-SULFONYL FLUORIDE-->Butyl glycidyl ether-->ETHYLENE TRITHIOCARBONATE |
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