96107-95-8

Basic information

• Product Name: Calix[6]arene
• Synonyms: Heptacyclo[31.3.1.1~3,7~.1~9,13~.1~15,19~.1~21,25~.1~27,31~]dotetraconta-1(37),3(42),4,6,9(41),10,12,15(40),16,18,21(39),22,24,27(38),28,30,33,35-octadecaene-37,38,39,40,41,42-hexol; heptacyclo[31.3.1.1~3,7~.1~9,13~.1~15,19~.1~21,25~.1~27,31~]dotetraconta-1(37),3,5,7(42),9,11,13(41),15,17,19(40),21,23,25(39),27,29,31(38),33,35-octadecaene-37,38,39,40,41,42-hexol; Heptacyclo[31.3.1.13,7.19,13.115,19.121,25.127,31]dotetraconta-1(37),3(42),4,6,9(41),10,12,15(40),16,18,21(39),22,24,27(38),28,30,33,35-octadecaene-37,38,39,40,41,42-hexol
• CAS NO: 96107-95-8
• Molecular Formula: C₄₂H₃₆O₆
• Molecular Weight: 636.7316
• Product Categories: Calixarenes;Functional Materials;Macrocycles for Host-Guest Chemistry;Chelation/Complexation Compounds;Synthetic Reagents
• Mol File: 96107-95-8.mol

Chemical Properties

• Melting Point: 395 °C(lit.)
• Boiling Point: 788.8°C at 760 mmHg
• Flash Point: 316.8°C
• Density: 1.302g/cm³
• Vapor Pressure: 7.9E-26mmHg at 25°C
• Refractive Index: 1.688
• PKA: 9.20±0.20(Predicted)
• Water Solubility: 0.180g/100g of water @ 25°C. Miscible with alcohol, chloroform, ether, carbon disulfide, acetone, oils, carbon tetrachloride and glacial acetic acid.
• BRN: 4345238
• CAS DataBase Reference: Calix[6]arene(CAS DataBase Reference)
• NIST Chemistry Reference: Calix[6]arene(96107-95-8)
• EPA Substance Registry System: Calix[6]arene(96107-95-8)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 22-24/25
• WGK Germany: 3
• Hazardous Substances Data: 96107-95-8(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
Calix[6]arene is used as a pharmaceutical intermediate for the development of drug delivery systems and as a host molecule for the complexation of various guest molecules, such as metal ions and organic compounds.
Used in Supramolecular Chemistry:
Calix[6]arene is used as a starting material for preparing functionalized calixarenes, which can be further modified to create new supramolecular systems with specific binding properties and selectivity.
Used in Organic Synthesis:
Calix[6]arene is used as a versatile building block in organic synthesis, allowing for the creation of a wide range of complex organic molecules with potential applications in various fields, such as materials science, catalysis, and medicinal chemistry.
Overall, Calix[6]arene is a versatile and promising compound with applications in various industries, including pharmaceuticals, supramolecular chemistry, and organic synthesis. Its unique properties and ability to form complexes with a wide range of guest molecules make it an attractive candidate for the development of new materials and technologies.

Upstream product

• 98-54-4 para-tert-butylphenol 
• 106-95-6 allyl bromide 
• 106750-72-5 37,38,39,40,41,42-hexabenzoyloxy[6]arene 
• 106750-71-4 37,38,39,40,41,42-hexaacetoxycalix[6]arene 
• 189832-67-5 5,11,17,23,29,35-hexakis(tert-butyl)-37,38,39,40,41-hexakis(hydroxy)calix[6]arene 

Downstream Products

• 123240-82-4 37,38,39,40,41,42-hexaethoxycalix{6}arene 
• 123264-02-8 37,38,39,40,41,42-hexa-n-octyloxycalix{6}arene 
• 123264-03-9 37,38,39,40,41,42-hexakis-(1-n-hexadecyloxy)calix[6]arene 
• 93503-76-5 5,11,17,23,29,35-hexakis(1,1-dimethylpropyl)-37,38,39,40,41,42-hexahydroxycalix<6>arene 
• 189832-67-5 5,11,17,23,29,35-hexakis(tert-butyl)-37,38,39,40,41-hexakis(hydroxy)calix[6]arene 
• 104789-79-9 p-isopropyl calix[6]arene 
• 192661-52-2 37,38,39,40,41,42-hexakis(5,5-dimethyl-1-hexyloxy)calix[6]arene 
• 799765-05-2 (C₆H₃(OCH₂CH₂OCH₂C(O)N(C₂H₅)2)CH₂)6 
• 870777-58-5 37,40-bis[(4-methylbenzyl)oxy]-38,39,41,42-tetrahydroxycalix[6]arene 

Relevant articles and documents

Synthesis and alkali metal ion binding properties of two rigid sterochemical isomers of calix[6]arene bis-crown-4

Cone and 1,2,3-alternate stereochemical isomers of 37,40-diallyloxy-(38,42),(39,41)-bis-crown-4 calix[6]arene, 3 and 4 were isolated in moderate yields by bridging the dialkylated calix[6]arene 2 with triethylene glycol di-p-tosylate. The alkali metal complex stoichiometries, association constants, and ion selectivities of 3 and 4 were studied by 1H NMR titration experiments, liquid - liquid extraction, electrospray ionization mass spectroscopy, and X-ray crystallography. Good agreement between the gas-phase and solution-phase studies regarding these metal binding properties was observed. Both conformers formed 1:1 complexes with all alkali metal ions but were structurally preorganized such that each exhibited a strong preference for the larger cesium ion as evidenced by the "deep-cavity" cesium complex of host 4, wherein π-metal interactions helped to stabilize the complex. The Cs+/Na+ selectivity factor for 4 was found to be 1500, while that of 3 was only 140.

Synthesis and investigation of catalytic affinities of water-soluble amphiphilic calix[n]arene surfactants in the coupling reaction of some heteroaromatic compounds

Six water-soluble calix[n]arene-based Br?nsted acid-type catalysts with amphiphilic groups were successfully synthesized by incorporating sulfonic acid moieties. Their structures were characterized using FTIR,1H NMR,13C NMR, APT-NMR, and elemental analysis techniques. Moreover, their catalytic capabilities were evaluated in the coupling reaction of 2-methylfuran and/or N-methylindole with some sec-alcohols in aqueous media. The association of their surfactant abilities, and the effects of water amount used and reaction durations on the catalytic activities of these amphiphilic calix[n]arene derivatives were also investigated. Observations indicated that these amphiphilic calix[n]arene catalysts exhibited high catalytic activities in the coupling reactions of 2-methylfuran and N-methylindole with some alcohols in water.

P-Sulfonic acid calix[4]arene-functionalized alkyl-bridged organosilica in esterification reactions

Two new p-sulfonic acid calix[4]arene- and p-sulfonic acid calix[6]arene-functionalized organosilica have been synthesized using a sol-gel method and applied as heterogeneous catalysts in esterification reactions. The catalytic performance was evaluated using the esterification of carboxylic acids with ethanol, and good catalytic activity (i.e., 55-88%) was observed under the optimum reaction conditions. This study reports the first promising example of the successful employment of calix[n]arenes as a heterogeneous catalyst for catalytic esterification. The catalyst was easily separated by filtration and reused five times without any significant loss of activity.

Calix[n]arenes: Active organocatalysts for the synthesis of densely functionalized piperidines by one-pot multicomponent procedure

An efficient, suitable and high yielding method has been developed for the synthesis of different densely functionalized piperidine derivatives via pseudo-five component, one-pot domino reaction through a combination of β-ketoesters, aromatic aldehydes, and various amines using p-sulfonic acid calix[n]arenes as catalysts. The reaction was carried out in refluxing methanol, affording very good yields of the expected piperidine. Atomic economy, environmentally benign procedure, reuse of catalysts, and short reaction time are some of the important features of this protocol.

Synthesis, X-ray crystal structure and anti-tumor activity of calix[n]arene polyhydroxyamine derivatives

Calixarene-based compounds are highly effective therapeutic agents against cancer. This study aims to prepare a series of calix [n]arene (n?=?4, 6, 8) polyhydroxyamine derivatives (3a–3m) and to study their potential antitumor activities. The single crystal structure of calixs[4]arene derivative 3a was determined through X-ray diffraction. We assessed the ability of the prepared calix [n]arene polyhydroxyamine derivatives to induce cytotoxicity in six cancer cell lines by performing cancer cell growth inhibition assays. Results demonstrated that compounds 3a–3d achieved IC50values ranging from 1.6?μM to 11.3?μM. Among the different compounds, 3a and 3b exerted the strongest cytotoxic effect in inhibiting the growth of SKOV3 cells. In relation to the underlying mechanisms of cytotoxic effects, cell cycle analysis revealed that the exposure of SKOV3 cells to 3a induced cell cycle arrest in the G0/G1 phase, suggesting a reduction in DNA synthesis. Immunofluorescent staining indicated that the protein expression levels of caspase-3 and p53 in cells significantly increased, whereas that of Bcl-2 was effectively suppressed. Meanwhile, no significant changes in Bax were observed in SKOV3 cells. These results highlight that calixarene 3a can be further studied as a potential anticancer agent.

Pb, Sr and Ba calix[6]arene hexacarboxylic acid octahedral complexation: A dramatic effect of dealkylation

Calix[6]arene hexacarboxylic acid binds instantly and with low symmetry to Pb, Sr and Ba. Later a highly symmetric up-down alternating conformation emerges. The solution structures are identical to their p-tert-butylcalix[6]arene hexacarboxylic acid counterparts. With either receptor, an octahedral cage is formed around the metal. The transformation from low to high symmetry however proceeds at significantly faster rates for the de-t-butylated host.

The synthesis of new calix[n]arene quaternary ammonium salts and investigation of their catalytic affinities for three component Mannich-type reactions in water

Two new calix[n]arenes and a non-cyclic analogue substituted with 1-(2-furoyl)piperazine have been synthesized. Moreover, their quaternary ammonium salts have been prepared by treatment with methyl iodide. All of the new quaternary ammonium salts have been employed as catalysts in one-pot Mannich reactions to afford β-aminocarbonyl compounds. The combination of good to excellent yields, the need for a small amount of catalyst and simple work-up, mean that this route can be considered to be green chemistry.

Br?nsted acidic magnetic nano-Fe3O4-adorned calix[n]arene sulfonic acids: Synthesis and application in the nucleophilic substitution of alcohols

Three magnetically recoverable Br?nsted acidic calix[n]arene derivatives were successfully constructed by immobilizing calix[n]arene sulfonic acids onto silica-coated magnetic nanoparticles, a process, which allows calix[n]arene derivatives to acquire magnetic properties. All of the magnetically recoverable Br?nsted acidic calix[n]arenes efficiently catalyze the coupling of electron-rich arenes with some alcohols in water. After separation and recovery from the reaction mixture by a simple magnet, these Br?nsted acidic calix[n]arenes can be recycled many times without losing their catalytic activity.

P-Sulfonic acid calix[n]arenes as homogeneous and recyclable organocatalysts for esterification reactions

Esterification yields were significantly improved using calix[n]arenes catalysts under simple conditions. p-Sulfonic acid calix[4]arene and p-sulfonic acid calix[6]arene were powerful organocatalysts in several esterification reactions, which showed activity comparable or even superior to other well-established acids catalysts, such as, sulfuric acid, p-toluenesulfonic acid, and p-hydroxybezenesulfonic acid described in the literature.

Study on thermal decomposition of calix[6]arene and calix[8]arene

Thermal decomposition kinetics of calix[6]arene (C6) and calix[8]arene (C8) were studied by Thermogravimetry analysis (TG) and Differential thermal analysis (DTA). TG was done under static air atmosphere with dynamic heating rates of 1.0, 2.5, 5.0, and 10.0 K min-1. Model-free methods such as Friedman and Ozawa-Flynn-Wall were used to evaluate the kinetic parameters such as activation energy (E a) and pre-exponential factors (ln A). Model-fitting method such as linear regression was used for the evaluation of optimum kinetic triplets. The kinetic parameters obtained are comparable with both the model-free and model-fitting methods. Within the tested models, the thermal decomposition of C6 and C8 are best described by a three dimensional Jander's type diffusion. The antioxidant efficiency of C6 and C8 was tested for the decomposition of polypropylene (PP).