60705-62-6

Usage

Uses

Used in Chemical Synthesis:
4-tert-Butylcalix[4]arene is used as a starting material for further derivatization in chemical synthesis processes. This includes halogenation, acylation, and diazo coupling, which allow for the creation of a wide range of chemical compounds with diverse properties and applications.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 4-tert-Butylcalix[4]arene is used as a building block for the development of new drugs and drug delivery systems. Its unique chemical properties make it a valuable component in the design and synthesis of novel therapeutic agents.
Used in Material Science:
4-tert-Butylcalix[4]arene is also utilized in material science for the development of advanced materials with specific properties. Its ability to undergo various chemical reactions allows for the creation of materials with tailored characteristics for use in different applications, such as sensors, catalysts, and advanced composites.
Used in Analytical Chemistry:
In analytical chemistry, 4-tert-Butylcalix[4]arene is employed as a selective receptor for the recognition and separation of various analytes. Its unique structure and chemical properties enable it to selectively bind to specific target molecules, making it a valuable tool in the development of new analytical methods and techniques.

Purification Methods

The calixarene recrystallises from CHCl3 in large solvated prisms (m 380o dec); it effloresces on drying in air. Its tetra-acetate crystallises from Ac2O in colourless prisms m 332-333o(dec). It crystallises from CCl4 or chlorobenzene /EtOH (m >300o) and the tetra-acetate crystallises from CHCl3/EtOH m >290o(dec). It also crystallises from toluene in white plates with toluene of crystallisation m 344-346o (330-332o); the tetra-acetate crystallises with 1AcOH of crystallisation m 383-386o (softening at 330-340o, also m 283-286o), but acetylation with Ac2O/NaOAc gives the triacetate which recrystallises from AcOH with 1AcOH of crystallisation m 278-281o. 4-tert-Butylcalix[4]arene (100mg) is unchanged after boiling for 4hours with 10N KOH (0.04mL) in xylene (4mL). [Br J Pharmacol 10 73 1955, K.mmerer et al. Monatsh Chem 109 767 1978, Gutsche et al. J Am Chem Soc 103 3782 1981; see also Kluawer in Calixarenes, Vicens & B.hner eds Academic Press 1991, Beilstein 6 IV 7858.]

InChI:InChI=1/C44H56O4/c1-41(2,3)33-17-25-13-27-19-34(42(4,5)6)21-29(38(27)46)15-31-23-36(44(10,11)12)24-32(40(31)48)16-30-22-35(43(7,8)9)20-28(39(30)47)14-26(18-33)37(25)45/h17-24,45-48H,13-16H2,1-12H3

Upstream product

• 50-00-0 formaldehyd 
• 98-54-4 para-tert-butylphenol 
• 2203-14-7 4-tert-butyl-2,5-bis(hydroxymethyl)phenol 
• 68803-63-4 3-<3-<3-(5-tert-butylsalicyl)-5-tert-butylsalicyl>-5-tert-butylsalicyl>-5-tert-butyl-2-hydroxybenzyl alcohol 
• 85097-23-0 7,13,21,27-tetra-tert-butyl-29,30,31,32-tetrahydroxy-2,3,16,17-tetrahomo-3,17-dioxacalix<4>arene 
• 138847-20-8 2C₄₄H₅₆O₄*C₂₈H₅₂N₂O₄ 
• 138847-16-2 C₄₄H₅₆O₄*C₉H₁₉N 
• 138847-18-4 C₄₄H₅₆O₄*C₉H₁₉NO 
• 138847-17-3 2C₄₄H₅₆O₄*C₉H₂₀N₂ 
• 138847-19-5 C₄₄H₅₆O₄*C₁₀H₂₁NO 
• 78-86-4 s-butyl chloride 
• 248590-47-8 25,26,27,28-tetrakis(hydroxy)calix[4]arene 
• 110-88-3 1,3,5-Trioxan 
• 81475-22-1 p-tert-Butylcalix[5]arene 

Downstream Products

• 99314-01-9 25,27-(3,6,9-trioxaundeca-1,11-diyl)oxy-26,28-dihydroxy-5,11,17,23-tetra-tert-butyl-calix[4]arene 
• 124657-96-1 3,7,25,29-tetrakis(1,1-dimethylethyl)-11,12,14,15,17,18,20,21,33,34,36,37,39,40,42,43-hexadecahydro-1,23:9,31-dimethano-5H,27H-tetrabenzo<1,4,7,10,13,19,22,25,28,31>decaoxacyclohexatriacontin 
• 122907-33-9 5,11,17,23-Tetra-tert.-butyl-25,26,27,28-tetrakis-(4'-hydroxy-3',5'-di-tert.-butylphenylcarboxy)-calix<4>aren 
• 137258-41-4 5,11,17,23-tetra-tert-butyl-25,27-bis((3,5-dinitro-4-(β-(dimethylamino)ethyl)benzoyl)oxy)-26,28-dihydroxycalix<4>arene 
• 137258-42-5 5,11,17,23-tetra-tert-butyl-25,27-bis((3,5-dinitro-4-vinyl-benzoyl)oxy)-26,28-dihydroxycalix<4>arene 
• 248590-47-8 25,26,27,28-tetrakis(hydroxy)calix[4]arene 
• 135501-31-4 5,11,17,23-tetra-tert-butyl-25,26,27,28-tetrakis(benzyloxy)calix<4>arene 
• 135288-40-3 proximal-2 
• 135501-37-0 5,11,17,23-tetra-tert-butyl-25,26,27-tris(benzyloxy)-28-hydroxycalix<4>arene 
• 113884-57-4 5,11,17,23-tetra-tert-butyl-25,26,27,28-tetra-(benzoyloxy)calix<4>arene 
• 128910-39-4 25,26-bis-O-(diethoxyphosphoryl)(p-tert-butyl)calix[4]arene 
• 129263-69-0 5,11,17,23-Tetra-tert.-butyl-25,26,27,28-tetrakis-(4'-hydroxy-3,5-di-tert.-butylphenylpropionyl)-calix<4>aren 
• 137571-15-4 11,23-di-tert-butylcalix<4>arene-25,26,27,28-tetrol 
• 180332-11-0 cone-5,11,17-tri-(tert-butyl)-28-hydroxycalix<4>arene 

Relevant academic research and scientific papers

Reversible coloring/decoloring reactions of thermochromic leuco dyes controlled by a macrocyclic compound developer

In this study, we examine macrocyclic compounds to determine whether they can provide a safer replacement and stable complex for BPA in thermochromic dyes. To achieve this objective, a series of macrocyclic compounds, Methyl-N-benzylhexahomotriazacalix[3]arene (MeAC3), p-Chloro-N-benzylhexahomo-triazacalix[3]arene (ClAC3), α-Cyclodexdrin (α-CD), β-Cyclodexdrin (β-CD), p-tert-Butylthiacalix[4]arene (TC4), Calix[4]arene (C4), and Resorcin[4]arene (RC4), were synthesized. Among these macrocyclic compounds, RC4 was determined to be the most appropriate candidate to replace BPA as the developer material used in thermochromic dyes. In tests of prepared thermochromic dyes, RC4 had results similar to those of BPA, achieving the best protonation/deprotonation equilibria and providing a dark contrast with the thermochromic dye. DFT calculations also showed stable complexes between RC4 and CVL via hydrogen-bond interactions.

Synthesis of new anthracene-conjugated calix[4]arene as highly selective fluorescent chemosensor for determination of CN? ion

A new calix[4]arene derivative substituted with anthracene at its 1,3-distal position was synthesized via a simple Schiff base reaction, and its structure was fully characterized by using ATR-FTIR, 1H-NMR, 13C-NMR, ESI-MS and elemental analysis techniques. Furthermore, the ion binding feature of the anthracene substituted calix[4]arene (Ant-Calix) was evaluated against Br?, Cl?, F?, HSO4?, NO3? and CN? ions. Various aspects of anion sensing phenomena were deeply assessed, and the findings addressed that Ant-Calix exhibited excellent selectivity for CN? and could detect in a very low detection limit 92.4 nM. Beside, when CN? ion was bound to the probe Ant-Calix, a significant color change from light green to pink color was observed under UV light. The fluorescence data was also employed to calculate the binding stoichiometry and association constant of the complex obtained between Ant-Calix and cyanide ion. In addition, the 1H-NMR technique was also used to elucidate the mechanism of the complex formation between Ant-Calix and CN?.

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

Optimization of toxic metal adsorption on DEA-calix[4]arene appended silica resin using a central composite design

The present study is devoted to the application of Central Composite Design (CCD) to purify water contaminated with toxic metal ions (Pb2+, Cd2+ and Hg2+) using a p-tert-diethanolaminomethylcalix[4]arene (DEA-C4) based silica resin. The synthesized material was characterized using SEM, FTIR and EDX techniques. Three effective parameters (pH, adsorbent dosage and concentration of metal ion) were optimized by assessment with CCD. The data was analyzed using the quadratic model and the obtained results revealed the highest % adsorptions for Pb2+ (92.7), Cd2+ (93.7) and Hg2+ (88.2) at the optimum points for pH (5.4, 3.18 and 3.89), adsorbent dosage (23.8, 25.5 and 26.12 mg) and metal ion concentration (5.3, 7.62 and 7.18 ppm), respectively. Analysis of variance (ANOVA) results show a good fit for the regression model, showing R2 values of 0.99 for Pb2+, 0.99 for Cd2+ and 0.98 for Hg2+. Furthermore, the results from Freundlich adsorption isotherms suggest its favorability, as the values for n are >1 (i.e., 7.06, 8.85 and 13.2) and there are higher values for R2 = 0.97, 0.99 and 0.98 for Pb2+, Cd2+ and Hg2+, respectively. However, for the Langmuir isotherm, the value of the separation factor RL is >1 (1.01, 1.02 and 1.05 for Pb2+, Cd2+ and Hg2+, respectively), revealing its un-favorability. In kinetics, the pseudo-second-order kinetic model (Ho and McKay) shows R2 values of 0.998, 0.999 and 0.999 for Pb2+, Cd2+ and Hg2+, suggesting the chemical reaction seems significant in the rate controlling step. The thermodynamic results concluded that the reaction is spontaneous and exothermic in nature.

Mathematical modeling studies for the adsorptive removal of ciprofloxacin drug from water samples using functionalized silica resin

The current research demonstrates the adsorptive removal of ciprofloxacin antibiotic drug from pharmaceutical wastewater samples using functionalized silica (FS) resin through batch adsorption experiments. The adsorption experiments were performed under the optimized parameters such as pH effect, FS-resin amount, ciprofloxacin concentration, equilibrium time and temperature. Results demonstrate that the maximum adsorption of ciprofloxacin was achieved at pH (6.5), while the effective resin dose was 20?mg?L?1. The Langmuir and Freundlich models were applied on equilibrium data, and it has been observed that the adsorption was best fit to the Freundlich model with a good correlation coefficient (R2 = 0.999). Moreover, the thermodynamic and kinetic parameters show that the adsorption of ciprofloxacin is endothermic and spontaneous in nature followed by pseudo-second-order kinetic model. To explore the efficiency of resin, the real wastewater samples were collected and it has been observed that resin has better potential to treat pharmaceutical effluents. Furthermore, the FS-resin and ciprofloxacin interaction were analyzed at a molecular level through quantum chemical calculation. Graphical abstract: [Figure not available: see fulltext.]

Viologen-cucurbituril host/guest chemistry - redox control of dimerizationversusinclusion

Two calix[4]arene systems,C234+andC244+- where 2 corresponds to the number of viologen units and 3-4 corresponds to the number of carbon atoms connecting the viologen units to the macrocyclic core - have been synthesized and led to t

Synthesis of new anthracene-substituted calix[4]triazacrown-5 as highly sensitive fluorescent chemosensor and extractant against hazardous dichromate anion

A new fluorogenic anthracene functionalized calix[4]triazacrown-5 (Ant-AzClx) was successfully synthesized using a simple Schiff’s base reaction. The 1H-NMR, 13C-NMR, ESI-MS, and elemental analysis techniques were performed to characterize its structure. Excited at 370 nm, Ant-AzClx reveals excimer emission at 418 nm. Therefore, its anion binding properties were investigated against F?, HCO3?, H2PO4?, NO3?, Cr2O72?, and SO42? ions. When hazardous dichromate anion was introduced into medium, the fluorescence intensity of Ant-AzClx was markedly quenched. The binding constant, stoichiometry, the detection limits and Stern–Volmer equation for the complex formed between Ant-AzClx and Cr2O72? ion were determined. Furthermore, the 1H-NMR technique was also performed to assess the mechanism of the complex (Ant-AzClx@Cr2O72?). Apart from its excellent fluorescent chemosensor properties for selective and sensitive recognition of Cr2O72? ion, Ant-AzClx was used as an efficient extractant towards dichromate anion. The extraction results indicated that Ant-AzClx exhibited high extraction capability, leading to it being a promising extractant for the removal of dichromate anions from water.

Columnar self-assembly, electrochemical and luminescence properties of basket-shaped liquid crystalline derivatives of Schiff-base-moulded: P-tert -butyl-calix[4]arene

A new family of supramolecular liquid crystalline compounds with a calix[4]arene core and two linking groups appended on four sides, exhibiting a wide range of hexagonal columnar phases, has been synthesised and well characterised. The liquid crystal beha

Turn on fluorescence strip based sensor for recognition of Sr2+ and CN? via lowerrim substituted calix[4]arene and its computational investigation

Fluorescence sensor L designed around a calix[4]arene scaffold, bearing two fluorogenic aminoquinoline moities, has been synthesized. It is found to be selective and sensitive towards Sr2+ and CN? over a wide range of cations and anions in a spectrofluorometric study in acetonitrile. The ion-binding property of L was monitored by fluorescence spectroscopy, UV–vis spectroscopy, ESI-MS, 1H NMR, FT-IR investigation and PXRD study. The host L shows a minimum detection limit which is 1.36 nM for Sr2+ and 1.23 nM for CN? having concentration range 5–120 nM and 5–115 nM respectively. The calculated binding constants for L:Sr2+ and L: CN? are respectively 8.859 × 108 M?1 and 8.574 × 108 M?1. Our host L has been utilised in formation of a user-friendly, affordable, and disposable paper-based analytical device (PAD) for rapid chemical screening of Sr2+ and CN? ion via single strip. Moreover, the optimization of probe L has also been done by the MOPAC-2016 software package using NM7 popular method resulting ?21.71 kcals/mol heat of formation and also determined the HOMO-LUMO energy band gap for L, L:Sr2+ and L: CN?. Further, molecular docking score has been calculated using HEX software. The applicability of our probe in real samples containing Sr2+ and CN? has also been checked by emission study with 94–99% recovery.

CALIXCROWNS AND USES THEREOF

Provided herein are novel calixcrowns, such as those of Formula (I), which are useful for coating a solid substrate such as a protein chip, diagnostic kit or protein separation pack. Also provided herein are methods detecting protein-protein interactions with a solid substrate coated with the calixcrown herein and an immobilized protein.