311-28-4 Usage
Chemical Properties
Tetrabutylammonium iodide is an organic ammonium compound with the molecular formula C16H36IN. white or tan powder. Soluble in water and ethanol, slightly soluble in chloroform and benzene. Stable under normal temperature and pressure.
Uses
Tetrabutylammonium iodide is used in the preparation of novel quaternary amines to serve as antibacterial agents in the rise of drug-resistant bacteria,it is also used in phosphonium reversible inhibitors of cholinesterases.
Application
Tetrabutylammonium iodide may be used as a mobile phase additive in ion-pair high-performance liquid chromatography (IP-HPLC) assay of 4-aminopyridine in serum. It may also be used as a mobile phase additive in the analysis of tetracycline by reversed-phase IPC. The addition of tetrabutylammonium iodide regulates the retention of tetracyclines.Tetrabutylammonium iodide can be used:As an additive in the synthesis of fused triazole derivatives using palladium catalyst.To prepare allyl-PEG-allyl, which is a key intermediate polymer used to synthesize fluorinated amphiphilic copolymers.As a catalyst used in the synthesis of ethers.
Reactions
Tetrabutylammonium iodide (TBAI) has been used as a catalyst in the following reactions:Synthesis of O-benzyl-N-Boc-L-tyrosine benzyl ester from N-Boc-L-tyrosine.Conversion of 8-fluoro-1-aminonaphthalene into 1-(8-fluoro-naphthalen-1-yl)piperazine hydrochloride.Synthesis of 1-(2,4-dichlorophenyl)-5-(4-(4-iodobut-1-ynyl)phenyl)-4-methyl-N-(piperidin-1-yl)-1H-pyrazole-3-carboxamide from 4-(4-(1-(2,4-dichlorophenyl)-4-methyl-3-(piperidin-1-ylcarbamoyl)-1H-pyrazol-5-yl)phenyl)but-3-yn-1-yl methanesulfonate.Other reactions where TBAI can be used as a catalyst:TBAI-tert-butyl hydroperoxide system can catalyze the conversion of α-methyl styrene derivatives into allylic sulfones by reacting with sulfonylhydrazides under metal-free conditions.Palladium(0)-catalyzed cross-coupling between benzylic zinc bromides and aryl or alkenyl triflates.Three-component coupling of amines, carbon dioxide, and halides to form carbamates in the presence of cesium carbonate.
General Description
Tetrabutylammonium iodide is a quaternary ammonium salt used in phase-transfer reactions. It is also used in regioselective ether cleavage reactions and as a source of iodide for nucleophilic displacement reactions.
Flammability and Explosibility
Notclassified
Purification Methods
Crystallise the iodide from toluene/pet ether (see entry for the corresponding bromide), acetone, ethyl acetate, EtOH/diethyl ether, nitromethane, aqueous EtOH or water. Dry it at room temperature under a vacuum. It has also been dissolved in MeOH/acetone (1:3, 10mL/g), filtered and allowed to stand at room temperature to evaporate to ca half its original volume. Distilled water (1mL/g) is then added, and the precipitate is filtered off and dried. It can also be dissolved in acetone, precipitated by adding ether and dried in a vacuum at 90o for 2 days. It has also been recrystallised from CH2Cl2/pet ether or hexane, or anhydrous methanol and stored in a vacuum desiccator over H2SO4. [Chau & Espenson J Am Chem Soc 108 1962 1986, Beilstein 4 IV 558.]
Check Digit Verification of cas no
The CAS Registry Mumber 311-28-4 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 3,1 and 1 respectively; the second part has 2 digits, 2 and 8 respectively.
Calculate Digit Verification of CAS Registry Number 311-28:
(5*3)+(4*1)+(3*1)+(2*2)+(1*8)=34
34 % 10 = 4
So 311-28-4 is a valid CAS Registry Number.
InChI:InChI=1/C16H36N.HI/c1-5-9-13-17(14-10-6-2,15-11-7-3)16-12-8-4;/h5-16H2,1-4H3;1H/q+1;/p-1
311-28-4Relevant articles and documents
Chiral benzimidazole derived bis-phenyl triazoles as chiroptical sensors for iodide and chiral amines
John, Marina E.,Karnik, Anil V.
supporting information, p. 2844 - 2853 (2020/05/25)
A series of chiral 2-hydroxy ethyl/benzyl benzimidazole based aryl triazole tweezers have been prepared using click chemistry in high yields. Chiral pool strategy has been used to obtain the benzimidazole-based tweezers in very high enantiomerically enriched form. The aryl triazole tweezers, S-(?)-5a and S-(+)-8a displayed a high degree of selectivity for iodide anion over other anions, including other halides. The aryl triazole tweezers, S-(?)-5a and S-(+)-8a display significant enantio-discrimination for chiral amines. The chiral recognition studies were carried out using UV and circular dichroism (CD) spectroscopy. NMR analysis has been used for establishing the sites for ligation of the iodide anion.
Silver (I) activated quaternization of tertiary amines by alkyl iodides: Overall analysis coupling homogeneous and heterogeneous processes
Santos, M. Soledade C.S.,Barbosa, Ester F.G.
experimental part, p. 106 - 113 (2012/04/17)
Kinetic data for the silver (I) activated homogeneous and heterogeneous quaternization of tributylamine by alkyl iodides in toluene is presented. Silver iodide was used as a solid catalyst. Solution and surface parameters were obtained applying the multistep kinetic model, previously proposed by Santos and Barbosa. A scrutiny of the derived quantities evidences competing structural and electronic effects. The solution reaction is dominated by structural factors while electronic effects govern the surface process. An overall analysis considering data from triethylamine systems, earlier investigated, allowed the establishment of a parallelism between the homogeneous and heterogeneous processes. A molecular level study involving size, shape and orientation of the chemical species on the surface, lead to estimates of interfacial layer thicknesses. A combination of surface parameters superficial reacting monolayer thicknesses and, the parallelism between homogeneous and heterogeneous catalysis consented the evaluation of "volumetric surface rate constants" which are directly comparable with their solution counterparts.
The 2-indenylidene chloropalladate {PdCl[Ind(Ph2P=S) 2]}(n Bu4N): A versatile pincer complex with "innocent" and "noninnocent" behavior
Oulie, Pascal,Nebra, Noel,Ladeira, Sonia,Martin-Vaca, Blanca,Bourissou, Didier
experimental part, p. 6416 - 6422 (2012/01/31)
The chloropalladate pincer complex {PdCl[Ind(Ph2P=S) 2]}(nBu4N) (2) has been prepared, and its reactivity has been thoroughly investigated. Alkyl halides such as iodomethane and benzyl chloride react at the electron-rich 2-indenylidene moiety, leading to the 2-indenyl pincer complexes {PdI[Ind(Me)(Ph2P=S)2]} (3) and {PdCl[Ind(Bn)(Ph2P=S)2]} (4), respectively. The ligand backbone is also involved in the reaction of 2 with the electron-deficient alkyne MeCO2C≡CCO2Me. Formally, one of the pincer ligand side arms is elongated and the original complex 5, featuring three fused metallacycles, is obtained. Nucleophiles such as PPh3 and NHCy 2 also react readily with 2, to give the corresponding 2-indenylidene complexes by displacement of the chloride at Pd. In addition, treatment of 2 with PhC≡CLi affords {Pd(C≡CPh)[Ind(Ph2P=S) 2]}(nBu4N) (8), the first alkynylpalladate to be isolated. All the new compounds have been characterized by multinuclear NMR spectroscopy and mass spectrometry. The structures of complexes 3, 5, and 8 have been further analyzed by means of X-ray diffraction studies.
