5271-60-3

Usage

Uses

Used in Organic Synthesis:
TBTOS is utilized as a catalyst in organic synthesis, particularly for olefin polymerization and oligomerization reactions. Its role in these processes is to facilitate the formation of new chemical bonds, leading to the creation of a wide range of industrial and consumer products.
Used in Silicone Production:
TBTOS is also employed in the production of silicones, which are a class of polymers known for their exceptional thermal stability, low toxicity, and resistance to water. These properties make silicones valuable in a variety of applications, from medical devices to construction materials.
Used in Organometallic Compounds Production:
The reactivity of TBTOS makes it a key component in the synthesis of organometallic compounds, which are compounds containing at least one metal-carbon bond. These compounds are essential in various chemical processes and are used in the production of pharmaceuticals, agrochemicals, and materials for the electronics industry.
Environmental and Health Concerns:
While TBTOS has significant industrial applications, it has also raised concerns due to its potential environmental and health effects. It is considered a marine pollutant and an endocrine disruptor, which can interfere with the hormonal systems of both humans and wildlife. As a result, there is a need for careful management and disposal of TBTOS to minimize its impact on the environment and human health.

InChI:InChI=1/4C4H9.2C2H4O2.2Sn/c4*1-3-4-2;2*3-1-2-4;;/h4*1,3-4H2,2H3;2*1-2H2;;/q;;;;2*-2;2*+2/rC20H44O4Sn2/c1-5-9-17-25(18-10-6-2)21-13-15-23-26(19-11-7-3,20-12-8-4)24-16-14-22-25/h5-20H2,1-4H3

Upstream product

• 818-08-6 di(n-butyl)tin oxide 
• 107-21-1 ethylene glycol 

Downstream Products

• 52767-61-0 1,2-ethandiyl bis(2-hydroxyacetate) 

Relevant academic research and scientific papers

Kinetic and biocompatibility investigation on the catalytic ring opening polymerization of L-lactide in bulk using cyclic Bu2Sn initiators derived from ethylene glycol, pentaerythritol and cloisite 30B

In the present work, considering a green approach, PLLA was synthesized by the ring-opening polymerization of L-LA using various cyclic initiators (2,2-dibutyl-2-stanna-1,3-dioxacyclo ethane (1), spirocyclic tin (3) and cloisite modified tin (5)). PLLA was characterized by size exclusion chromatography, differential scanning calorimetry, 1H and 13C NMR, XRD and MALDI-TOF. The molecular weight distribution was narrow (85,000 g/mol). An X-ray study showed the crystalline nature of PLLA, irrespective of the different types of initiators and polymerization conditions. A kinetic investigation showed that all polymerizations were first order with respect to the monomer and no termination reactions occurred during the polymerization. MALDI-TOF spectra of PLLA chains doped with Na+ and K+ cations show that the PLLA prepared using initiators 1 and 3 have hydroxyl and carboxyl end groups without incorporation of tin. The MALDI-TOF spectrum of PLLA prepared using initiator 5 also enabled the simultaneous detection of the linear and cyclic structure of PLLA without tin. Biocompatible and biodegradable PLLA was obtained, which could be used for biomedical applications.

High-yield synthesis of the enterobactin trilactone and evaluation of derivative siderophore analogs

A novel one-step synthesis of the macrocyclic triserine trilactone scaffold of the siderophore enterobactin, which eliminates the β-lactonization step of N-tritylserine, is presented. The cyclization reaction is based on a stannoxane template and leads to an overall yield of ~ 50%. This enables the practical functionalization of the trilactone by attaching chelating groups other than catecholamides. The conformational stability of the trilactone ring has been examined by high-resolution X-ray diffraction studies of the N-trityl intermediate: crystals grown from methylene chloride:methanol are orthorhombic, space group P212121 With unit cell dimensions a = 9.2495(5) A?, b = 11.3584(1) A?, c = 48.945(1) A?, V = 5142.1(2) A?3, and Z = 4. A hydroxypyridinonate analog of enterobactin, N,N',N''-tris[(3-hydroxy-1-methyl-2-oxo-(1H-pyridinyl)carbonyl]-4-cyclotriseryl trilactone (hopobactin), has been prepared by attachment of three 3-hydroxy-1-methyl-2(1H)-pyridinonate (3,2-HOPO) moieties to the triserine trilactone. This ligand represents the first enterobactin analog that retains the trilactone scaffold, but employs chelates other than catecholamides. Crystals of the chiral ferric complex grown from DMF:diethyl ether are monoclinic, space group P21, with unit cell dimensions a 13.0366(9) A?, b = 22.632(2) A?, c = 27.130(2) A?, b = 100.926(1)(o), V = 7860(1) A?3, and Z = 8. The Δ configuration of enterobactin metal complexes is also enforced in those of hopobactin and persists in aqueous or methanolic solution, as demonstrated by circular dichroism. The ferric hopobactin complex is the first reported chiral complex of hydroxypyridinonate ligands. The solution coordination chemistry of this new ligand and its iron(III) and iron(II) complexes have been studied by means of 1H NMR, potentiometric, spectrophotometric, and voltammetric methods. The average protonation constant of the hopobactin free ligand (log K(av) = 6.1) is typical of other 3-hydroxy-1-methyl-2-oxo-1H-pyridin-4-carboxamide ligands. The stability constants of the iron(III) complex formed with hopobactin (log β110 = 26.4) and with the tris(2-aminoethyl)amine-based analog, TRENHOPO, (log β110 to = 26.7) are of the same order of magnitude, unlike the catecholamide-based species, where enterobactin (log β110 = 49) is 6 orders of magnitude more stable than TRENCAM (log β110 = 43.6). The stability enhancement reflects the specific predisposition by the triserine scaffold of the catecholamide binding units. In spite of a significantly lower affinity of 3,2-hydroxypyridinonates for iron(III) compared with the more basic catecholates, hopobactin is an extraordinarily powerful chelating agent under acidic conditions: No measurable dissociation is observed even in 1.0 M HCl. In contrast to enterobactin and its synthetic derivatives, the hopobactin ferric complex undergoes no sequential protonation above pH 1. The affinity of hopobactin and TRENHOPO for iron(III) relative to iron(II) results in strongly negative reduction potentials, -782 mV vs 0.01 M Ag+/Ag in CH3CN or -342 mV vs NHE in water and -875 mV vs 0.01 M Ag+/Ag in CH3CN or -435 mV vs NHE in water, respectively.