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
• Article Data: 18

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

Chemical Properties

white to beige powder

Uses

It is used as a starting material for preparing functionalized calixarenes. It finds its uses as a pharmaceutical intermediate. It is also used in complexation and organic synthesis.

Upstream product

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

Downstream Products

• 133708-88-0 hexa-p-dodecanoyl-calix[6]arene 
• 97600-46-9 hexamethyl calix<6>arene hexaacetate 
• 97600-45-8 37,38,39,40,41,42-Hexaethoxycarbonylmethyleneoxycalix[6]arene 
• 1422251-67-9 calix[6]arene 
• 1268723-06-3 C₉₀H₁₂₀O₁₂ 
• 1268723-01-8 C₆₆H₇₂O₁₂ 
• 1313490-04-8 5,11,17,23,29,35-hexabromo-37,38,39,40,41,42-hexabutoxycalix[6]arene 
• 123240-83-5 37,38,39,40,41,42-hexabutoxycalix<6>arene 
• 245049-23-4 C₄₂H₃₀O₆P₂ 
• 171797-88-9 5,11,17,23,29,35-hexabromo-37,38,39,40,41,42-hexahydroxycalix[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.

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.

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.