311-28-4 Usage
Description
Tetrabutylammonium iodide is a quaternary ammonium salt with the molecular formula C16H36IN, which is an organic ammonium compound. It appears as a white or tan powder and is soluble in water and ethanol, slightly soluble in chloroform and benzene. Tetrabutylammonium iodide is stable under normal temperature and pressure and is widely used in various chemical reactions and applications due to its unique properties.
Uses
Used in Pharmaceutical Industry:
Tetrabutylammonium iodide is used as a catalyst in the synthesis of novel quaternary amines, which serve as antibacterial agents. This is particularly important in the context of the rise of drug-resistant bacteria, where new and effective antibacterial compounds are crucial.
Used in Enzyme Inhibition:
In the field of biochemistry, Tetrabutylammonium iodide is utilized as a phosphonium reversible inhibitor of cholinesterases, which are essential enzymes in the nervous system. This application can be valuable in studying the function of these enzymes and developing potential therapeutics for related conditions.
Used in Analytical Chemistry:
Tetrabutylammonium iodide may be employed as a mobile phase additive in ion-pair high-performance liquid chromatography (IP-HPLC) assays, such as the analysis of 4-aminopyridine in serum. It can also be used in the analysis of tetracycline by reversed-phase IPC, where the addition of the compound helps regulate the retention of tetracyclines.
Used in Organic Synthesis:
As an additive in the synthesis of fused triazole derivatives using palladium catalyst, Tetrabutylammonium iodide plays a crucial role in the formation of these complex organic molecules, which have potential applications in various industries, including pharmaceuticals and materials science.
Used in Polymer Synthesis:
Tetrabutylammonium iodide is used to prepare allyl-PEG-allyl, a key intermediate polymer in the synthesis of fluorinated amphiphilic copolymers. These copolymers have a range of applications, such as in drug delivery systems and as components in advanced materials.
Used as a Catalyst:
In the synthesis of ethers, Tetrabutylammonium iodide can be employed as a catalyst, facilitating the reaction and improving the overall efficiency of the process.
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.
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.
The triple role of fluoride ions in palladium-catalyzed Suzuki-Miyaura reactions: Unprecedented transmetalation from [ArPdFL2] complexes
Amatore, Christian,Jutand, Anny,Leduc, Gaatan
, p. 1379 - 1382 (2012/03/27)
Fluoride ions play three roles in the Suzuki-Miyaura reaction. They favor the reaction by formation of trans-[ArPdF(PPh3)2], which reacts with Ar B(OH)2 in an unprecedented rate-determining transmetalation, and by promoting the reductive elimination from the trans-[ArPdAr (PPh3)2] intermediate. Conversely, F - disfavors the reaction by formation of unreactive anionic Ar B(OH)n-3Fn- (n=1-3), leading to two antagonistic effects of F- in the transmetalation. Copyright
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.