182496-55-5

Basic information

• Product Name: 4-TERT-BUTYLTHIACALIX[4]ARENE
• Synonyms: TETRA-TERT-BUTYL(TETRAHYDROXY)TETRATHIACALIX[4]ARENE;4-TERT-BUTYLTHIACALIX[4]ARENE;2,8,14,20-Tetrathiapentacyclo[19.3.1.13,7.19,13.115,19]octacosa-1(25),3,5,7(28),9,11,13(27),15,17,19(26),21,23-dodecaene-25,26,27,28-tetrol, 5,11,17,23-tetrakis(1,1-dimethylethyl)-;Cobalt(II) ionophore IV ;4-tert-Butylthiacalix[4]arene
• CAS NO: 182496-55-5
• Molecular Formula: C₄₀H₄₈O₄S₄
• Molecular Weight: 721.07
• Product Categories: Functional Materials;Macrocycles for Host-Guest Chemistry;Thiacalixarenes
• Mol File: 182496-55-5.mol

Chemical Properties

• Melting Point: 320-322 °C
• Boiling Point: 735.4°C at 760 mmHg
• Flash Point: 355.6°C
• Appearance: /
• Density: 1.221g/cm³
• Vapor Pressure: 2.33E-22mmHg at 25°C
• Refractive Index: 1.637
• Solubility: soluble in Chloroform
• PKA: 7.33±0.20(Predicted)
• CAS DataBase Reference: 4-TERT-BUTYLTHIACALIX[4]ARENE(CAS DataBase Reference)
• NIST Chemistry Reference: 4-TERT-BUTYLTHIACALIX[4]ARENE(182496-55-5)
• EPA Substance Registry System: 4-TERT-BUTYLTHIACALIX[4]ARENE(182496-55-5)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• Hazardous Substances Data: 182496-55-5(Hazardous Substances Data)

Usage

Uses

Used in Host-Guest Chemistry:
4-TERT-BUTYLTHIACALIX[4]ARENE is used as a host molecule for selectively binding guest molecules due to its large central cavity and non-covalent interaction capabilities, which is crucial for the development of supramolecular systems and molecular recognition processes.
Used in Supramolecular Chemistry:
In supramolecular chemistry, 4-TERT-BUTYLTHIACALIX[4]ARENE is utilized as a building block for constructing novel functional architectures. Its ability to form non-covalent interactions with other molecules allows for the creation of complex and dynamic assemblies.
Used in Molecular Recognition:
4-TERT-BUTYLTHIACALIX[4]ARENE is employed as a molecular recognition tool, leveraging its selective binding properties to identify and interact with specific target molecules, which is essential in various analytical and diagnostic applications.
Used in Material Science:
4-TERT-BUTYLTHIACALIX[4]ARENE is used as a component in the development of new materials, capitalizing on its unique structure and binding properties to create materials with tailored properties for specific applications.
Used in Research and Development:
In the scientific community, 4-TERT-BUTYLTHIACALIX[4]ARENE is used as a subject of research to explore its potential applications and to understand the underlying mechanisms of its interactions with various guest molecules, contributing to the advancement of multiple scientific and technological fields.

InChI:InChI=1/C40H48O4S4/c1-37(2,3)21-13-25-33(41)26(14-21)46-28-16-23(39(7,8)9)18-30(35(28)43)48-32-20-24(40(10,11)12)19-31(36(32)44)47-29-17-22(38(4,5)6)15-27(45-25)34(29)42/h13-20,41-44H,1-12H3

Upstream product

• 950778-60-6 C₄₂H₄₆F₆O₈S₆ 
• 100-46-9 benzylamine 

Downstream Products

• 204190-49-8 p-tert-butylsulfonylcalix[4]arene 
• 549504-21-4 26,28-dibenzyloxy-5,11,17,23-tetra-tert-butyl-2,8,14,20-tetrathiapentacyclo[19.3.1.1^3,7.1^9,13.1^15,19]octacosa-1⁽²⁵⁾,3,5,7⁽²⁸⁾,9,11,13⁽²⁷⁾,15,17,19⁽²⁶⁾,21,23-dodecaene-25,27-diol 
• 210706-03-9 5,11,17,23-tetra-tert-butyl-25,26,27,28-tetrakis[(ethoxycarbonyl)methoxy]-2,8,14,20-tetrathiacalix[4]arene 
• 270085-37-5 distal-5,11,17,23-tetra-tert-butyl-25,27-bis[(ethoxycarbonyl)methoxy]-26,28-dihydroxy-2,8,14,20-tetrathiacalix[4]arene 
• 911432-76-3 1,3-alternate-25,27-bis(benzyloxy)-26,28-diethoxy-5,11,17,23-tetra-tert-butyl-2,8,14,20-tetrathiacalix[4]arene 
• 911432-77-4 1,3-alternate-25,27-bis(benzyloxy)-26,28-dipropoxy-5,11,17,23-tetra-tert-butyl-2,8,14,20-tetrathiacalix[4]arene 
• 911432-78-5 1,3-alternate-25,27-bis(benzyloxy)-26,28-dibutoxy-5,11,17,23-tetra-tert-butyl-2,8,14,20-tetrathiacalix[4]arene 

Relevant articles and documents

Synthesis of mono- and 1,3-diaminocalix[4]arenes via ullmann-type amination and amidation of 1,3-bistriflate esters of calix[4]arenes

Practical methods are described for the preparation of monoamines 4 and 1,3-diamines 5, bearing one or two amino group(s) instead of the hydroxy group(s) at the 28-position or at both the 26- and 28-positions of p-tert-butylcalix[4]arene (1a) and p-tert-butylthiacalix[4]arene (1b), via the Ullmann-type amination or amidation. Thus, the copper-catalyzed or mediated amination of the 1,3-bistriflate ester (2a) of 1a with benzylamine affords either mono(benzylamino) triflate 7a or 1,3-bis(benzylamine) 8 in a high yield, depending on the reaction conditions. On the other hand, the 1,3-bistriflate ester (2b) of 1b resists disubstitution and produces, under stoichiometric conditions, mono(benzylamino) triflate 7b. The disubstitution of 2b is achieved by amidation with tosylamide, giving 1,3-bis(tosylamide) 17b. The hydrogenolysis of the benzylamino moiety of 7a, followed by the hydrolysis of the Tf moiety, affords monoamine 4a, while the hydrogenolysis of 8 affords 1,3-diamine 5a. The amino moiety of 7b can be deprotected under acidic conditions to give, after hydrolysis, monoamine 4b. The hydrolysis of 17b affords 1,3-diamine 5b. The overall yields of compounds 4a, 4b, 5a, and 5b are 72%, 45%, 78%, and 24%, respectively, based on commercially available compounds 1 and are much higher than the ones previously reported in the literature.

Casting heteracalixarenes from calixarene templates: A unique synthetic strategy

A simple, intuitive and modular strategy to synthesize higher heteracalixarene (in particular thiacalixarene) homologs using respective calixarene templates has been developed and demonstrated. The Royal Society of Chemistry.