68971-82-4

Basic information

• Product Name: 4-TERT-BUTYLCALIX[8]ARENE
• Synonyms: (49),3,5,7(56),9,11,13(55),15,17,19(54),21,23,25(53),27,29,31(52),33,35,37(51),;,41,47-octakis(1,1-dimethylethyl)-;3,1,13,7,19,13,115,19,121,25,127,31,133,37,139,43]hexapentaconta-1(49),3,5,7(56),9,11,13(55),15,Nonacyclo[43;39,41,43(50),45,47-tetracosaene-49,50,51,52,53,54,55,56-octol,5,11,17,23,29,35;nonacyclo[43.3.1.13,7.19,13.115,19.121,25.127,31.133,37.139,43]hexapentaconta-1;5,11,17,23,29,35,41,47-OCTA(TERT-BUTYL)NONACYCLO[43.3.1.1(3,7).1(9,13).1(15,19).1(21,25).1(27,31).1(33,37).1(39,43)]HEXAPENTACONTA-1(49),3(56),4,6,9(55),+;4-TERT-BUTYLCALIX[8]ARENE;4-T-BUTYLCALIX[8]ARENE
• CAS NO: 68971-82-4
• Molecular Formula: C₈₈H₁₁₂O₈
• Molecular Weight: 1297.83
• Product Categories: Calixarenes;Functional Materials;Macrocycles for Host-Guest Chemistry;Chelation/Complexation Compounds;Synthetic Reagents
• Mol File: 68971-82-4.mol

Chemical Properties

• Melting Point: 411-412 °C(lit.)
• Boiling Point: 845.32°C (rough estimate)
• Appearance: White to off-white/Micro-Crystalline Powder
• Density: 1.095±0.06 g/cm3 (20 ºC 760 Torr)
• Refractive Index: 1.6000 (estimate)
• PKA: 9.23±0.20(Predicted)
• BRN: 2612052
• CAS DataBase Reference: 4-TERT-BUTYLCALIX[8]ARENE(CAS DataBase Reference)
• NIST Chemistry Reference: 4-TERT-BUTYLCALIX[8]ARENE(68971-82-4)
• EPA Substance Registry System: 4-TERT-BUTYLCALIX[8]ARENE(68971-82-4)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• TSCA: Yes
• Hazardous Substances Data: 68971-82-4(Hazardous Substances Data)

Usage

Uses

Used in Supramolecular Chemistry:
4-tert-Butylcalix[8]arene is used as a host molecule for the formation of host-guest complexes with a variety of guest molecules, such as metal ions, organic molecules, and anions. Its ability to selectively bind and encapsulate guest molecules makes it a valuable tool in supramolecular chemistry for applications like molecular recognition, sensing, and drug delivery.
Used in Catalysts:
4-tert-Butylcalix[8]arene is used as a catalyst or catalyst support in various chemical reactions. Its cavity and functionalizable upper rim allow for the design of catalysts with specific selectivity and activity, making it useful in processes like esterification, transesterification, and hydrolysis.
Used in Separation Processes:
4-tert-Butylcalix[8]arene is used as a selective adsorbent or ionophore in separation processes, such as chromatography, membrane separation, and ion exchange. Its ability to selectively bind certain ions or molecules can be exploited to separate mixtures or purify specific components.
Used in Materials Science:
4-tert-Butylcalix[8]arene is used as a building block for the development of new materials with unique properties. Its ability to self-assemble and form complexes can be utilized to create supramolecular polymers, gels, and other functional materials with potential applications in areas like sensors, drug delivery, and nanotechnology.
Used in Starting Material for Derivatization:
4-tert-Butylcalix[8]arene serves as a starting material for further derivatization, including halogenation, acylation, and diazo coupling. These modifications can introduce new functional groups or alter the properties of the calixarene, expanding its potential applications and uses in various fields.

Purification Methods

The calixarene recrystallises from CHCl3 in fine colourless, glistening needles. It melts sharply between 400-401o and 411-412o depending on the sample and is sensitive to traces of metal ions. On TLC with silica gel (250\m thick) and elution with CHCl3/hexane (3:4) it has RF 0.75. The octa-acetate is prepared from 8g in Ac2O (50mL) and 2 drops of conc H2SO4 and refluxed for 2hours. On cooling, a colourless precipitate separates and is recrystallised from Ac2O (1.2g 48%) with m 353-354o. The (SiMe3)8 is prepared from 4-tert-butylcalix[8]arene (0.65g) in pyridine (4mL) with excess of hexamethyldisilazane (1mL) and trimethylchlorosilane (0.5mL) and refluxed under N2 for 2hours. Cool, evaporate the pyridine, triturate the gummy residue with MeOH. Chromatograph on silica gel using hexane/CH2Cl2 gave 0.5g (61%) with one spot on TLC. Recrystallise it from hexane/Me2CO to give colourless needles m 358-360o. [Gutsche et al. J Am Chem Soc 103 3782 1981, Gutsche & MuthuKrishnan J Org Chem 43 4905 1978, Gutsche & MuthuKrishnan J Org Chem 44 3962 1979, Andretti et al. J Chem Soc, Chem Commun 533 1981; see Kluawer in Calixarenes, Vicens & B.hner eds Academic Press 1991.]

InChI:InChI=1/C88H112O8/c1-81(2,3)65-33-49-25-51-35-66(82(4,5)6)37-53(74(51)90)27-55-39-68(84(10,11)12)41-57(76(55)92)29-59-43-70(86(16,17)18)45-61(78(59)94)31-63-47-72(88(22,23)24)48-64(80(63)96)32-62-46-71(87(19,20)21)44-60(79(62)95)30-58-42-69(85(13,14)15)40-56(77(58)93)28-54-38-67(83(7,8)9)36-52(75(54)91)26-50(34-65)73(49)89/h33-48,89-96H,25-32H2,1-24H3

Upstream product

• 110-88-3 1,3,5-Trioxan 
• 98-54-4 para-tert-butylphenol 
• 1130162-32-1 C₁₈₄H₂₂₄O₁₆S₈ 
• 50-00-0 formaldehyd 
• 421546-91-0 2,6-bis(methoxymethyl)-para-tert-butylphenol 
• 810-52-6 4-(tert-butyl)-2,6-bis{[5-(tert-butyl)-2-hydroxyphenyl]methyl}phenol 
• 81475-22-1 p-tert-Butylcalix[5]arene 
• 84161-29-5 5,11,17,23,29,35,41-heptakis(1,1-dimethylethyl)-43,44,45,46,47,48,49-heptahydroxy calix[7]arene 
• 78-86-4 s-butyl chloride 
• 82452-93-5 calix[8]arene 
• 136760-77-5 p-tert-butylcalix<8>arene - triethylamine 1:1 adduct 
• 138847-23-1 2C₈₈H₁₁₂O₈*C₉H₂₀N₂ 
• 138847-22-0 C₈₈H₁₁₂O₈*C₉H₁₉N 
• 138847-21-9 C₈₈H₁₁₂O₈*C₆H₁₃N 

Downstream Products

• 150919-08-7 1,3,5,7-tetrakis(p-methylbenzyl)-p-tert-butylcalix[8]arene 
• 168649-10-3 5,11,17,23,29,35,41,47-Octa-tert-butyl-49,51-bis[(4-methylbenzyl)oxy]calix[8]arene-50,52,53,54,55,56-hexol 
• 168649-09-0 5,11,17,23,29,35,41,47-Octa-tert-butyl-49-[(4-methylbenzyl)oxy]calix[8]arene-50,51,52,53,54,55,56-heptol 
• 1130162-26-3 C₁₈₄H₂₄₀O₁₆ 
• 1367887-21-5 C₁₄₀H₁₇₂N₄O₂₀ 
• 1367887-15-7 C₁₃₆H₁₆₄N₄O₂₀ 
• 1367887-27-1 C₁₄₄H₁₈₀N₄O₂₀ 
• 137407-62-6 p-sulfonatocalix[8]arene 
• 157432-87-6 5,11,17,23-tetra-t-butyl-25,26,27,28-tetrahydroxycalix-4-arene 

Relevant articles and documents

Inclusion complexes of water-soluble calix[n]arenes with quercetin: preparation, characterization, water solubility, and antioxidant features

This study focuses on the construction of two new inclusion complexes of quercetin with p-sulfonatocalix[4]arene-tetracarboxylic acid and/or p-sulfonatocalix[8]arene-octacarboxylic acid, so that the drug gets soluble in an aqueous media. The structures of

Path to Industrial Production of Calix[8 and 4]arenes

A highly selective and high yield synthesis for the production of calix[8]arenes in concentrated reaction masses is described. Obtained purities are >98% and yields of >80%, with isolation by simple filtration. The developed approach allows for subsequent

Calix[8]arene-based Ni(II) complexes for electrocatalytic CO2 reduction

The electrochemical behavior and catalytic activity for the electroreduction of CO2 of complexes of Ni(II) containing phenanthroline-based ligands, with or without a calixarene scaffold, were tested. The complexes were characterized by spectroscopic techniques, and their electrocatalytic properties determined by cyclic voltammetry. With water as proton source the complex [(1,5-(2,9-dimethyl-1,10-phenanthro)-p-tert-butylcalix[8]arene)NiCl2] (1) presented a significant increase in current at E = ?2.36 V (relative to Ag/AgCl reference electrode) when reduced under an atmosphere of CO2, indicating that an electrocatalytic process occurs. Thus, calix[8]arenes that feature a phenanthroyl moiety as bidentate N-ligands, and an intramolecular proton source in the phenolic –OH groups, afford Ni(II) electrocatalysts for the reduction of CO2.

MOLECULES THAT STIMULATE THE IMMUNE SYSTEM FOR TREATMENT OF DRUG ADDICTION, METHODS OF SYNTHESIS, ANTIDRUG VACCINE AND USES

This technology relates to immune system stimulating molecules to be used in the treatment of drug addiction and abuse and their synthesis processes. These molecules have a calixarene chemical structure, preferably calix[4]arene and/or calix[8]arene, coupled to an hapten analogous to cocaine, preferably GNE and/or GNC. An anti-drug vaccine, specifically anti-cocaine, is also described using such molecules. The anti-drug vaccine can be also used to prevent fetal exposure to drugs in pregnant women who use drugs and do not wish or cannot stop their use during pregnancy.

Calixarenes functionalised water-soluble iron oxide magnetite nanoparticles for enzyme immobilisation

In this study, we first used water-soluble iron oxide nanoparticles for Candida rugosa lipase immobilisation. Moreover, two new complexation phenomena of the prepared water-soluble Fe3O4 nanoparticles with an enzyme might address int

Efficient removal of pentachlorophenol from aqueous solution by 4-: Tert -butylcalix[8]arene modified thermally sensitive hydrogels

We prepared poly(N-isopropylacrylamide-co-4-tert-butylcalix[8]arene) (PNIPAM-TBCX) hydrogels by copolymerization of N-isopropylacrylamide (NIPAM) with 4-tert-butylcalix[8]arene (TBCX) to capture hazardous pentachlorophenol (PCP) from aqueous solution. Adsorption experiments showed that the adsorption capacities of PNIPAM-TBCX hydrogels reached 1.96, 2.08 and 2.02 mg PCP per 1 g of hydrogel, while the molar percentage ratio of TBCX in the hydrogels was as low as 0.5%, 0.7% and 1%. The equilibrium adsorption of PCP on the hydrogels was studied using different adsorption models. In addition, the PNIPAM-TBCX hydrogel still retained its performance when regenerated several times by immersing in water at 323 K.

Synthesis, luminescence, and electrochemical studies of tetra- and octanuclear ruthenium(ii) complexes of tolylterpyridine appended calixarenes

Tetra- and octanuclear Ru(ii) complexes of tolylterpyridine appended calixarenes, [{Ru(ttpy)}4(L1)](PF6)8 (3) and [{Ru(ttpy)}8(L2)](PF6)16 (4) [L1 = 5,11,17

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-tert-Butylcalix[8]arene catalysed synthesis of 3,5-dinitrothiophene scaffolds: Antiproliferative effect of some representative compounds on selective anticancer cell lines

A new efficient protocol for the synthesis of 3,5-dinitrothiophene scaffolds was developed by using simple p-tert-butylcalix[8]arene in aqueous medium. Biological activities of some representative compounds were also studied to inhibit the cell growth on selective anticancer cell lines.

Enhanced catalysis and enantioselective resolution of racemic naproxen methyl ester by lipase encapsulated within iron oxide nanoparticles coated with calix[8]arene valeric acid complexes

In this study, two types of nanoparticles have been used as additives for the encapsulation of Candida rugosa lipase via the sol-gel method. In one case, the nanoparticles were covalently linked with a new synthesized calix[8]arene octa valeric acid derivative (C[8]-C4-COOH) to produce new calix[8]arene-adorned magnetite nanoparticles (NP-C[8]-C4-COOH), and then NP-C[8]-C4-COOH was used as an additive in the sol-gel encapsulation process. In the other case, iron oxide nanoparticles were directly added into the sol-gel encapsulation process in order to interact electrostatically with both C[8]-C4-COOH and Candida rugosa lipase. The catalytic activities and enantioselectivities of two novel encapsulated lipases (Enc-NP-C[8]-C4-COOH and Enc-C[8]-C4-COOH@Fe 3O4) in the hydrolysis reaction of racemic naproxen methyl ester were evaluated. The results showed that the activity and enantioselectivity of the lipase were improved when the lipase was encapsulated in the presence of calixarene-based additives. Indeed, the encapsulated lipases have an excellent rate of enantioselectivity, with E = 371 and 265, respectively, as compared to the free enzyme (E = 137). The lipases encapsulated with C[8]-C4-COOH and iron oxide nanoparticles (Enc-C[8]-C 4-COOH@Fe3O4) retained more than 86% of their initial activities after 5 repeated uses and 92% with NP-C[8]-C 4-COOH. This journal is the Partner Organisations 2014.