458561-35-8

Basic information

• Product Name: tris[2,2,6,6-tetramethyl-8-(carboxy-tert-butyl)benzo[1,2-d;4,5-d]bis(1,3-dithiol)-4-yl]methanoltritylalcohol
• Synonyms: tris[2,2,6,6-tetramethyl-8-(carboxy-tert-butyl)benzo[1,2-d;4,5-d]bis(1,3-dithiol)-4-yl]methanoltritylalcohol
• CAS NO: 458561-35-8
• Molecular Weight: 885.516
• Mol File: 458561-35-8.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: tris[2,2,6,6-tetramethyl-8-(carboxy-tert-butyl)benzo[1,2-d;4,5-d]bis(1,3-dithiol)-4-yl]methanoltritylalcohol(CAS DataBase Reference)
• NIST Chemistry Reference: tris[2,2,6,6-tetramethyl-8-(carboxy-tert-butyl)benzo[1,2-d;4,5-d]bis(1,3-dithiol)-4-yl]methanoltritylalcohol(458561-35-8)
• EPA Substance Registry System: tris[2,2,6,6-tetramethyl-8-(carboxy-tert-butyl)benzo[1,2-d;4,5-d]bis(1,3-dithiol)-4-yl]methanoltritylalcohol(458561-35-8)

Safety Data

• Hazardous Substances Data: 458561-35-8(Hazardous Substances Data)

Upstream product

• 447463-65-2 1,2,4,5-tetrakis(tert-butylthio)benzene 

Downstream Products

• 910912-05-9 bis(8-ethoxycarbonyl)tris(2,2,6,6-tetramethylbenzo[1,2-d;4,5-d']bis[1,3]dithiol-4-yl)methanol 
• 76-84-6 triphenylmethyl alcohol 
• 447463-75-4 tris[8-ethoxycarbonyl-2,2,6,6-tetramethylbenzo[1,2-d:4,5-d']bis-([1,3]dithiole)-4-yl]methanol 

Relevant articles and documents

Trityl Radicals with a Combination of the Orthogonal Functional Groups Ethyne and Carboxyl: Synthesis without a Statistical Step and EPR Characterization

Finland trityl radical (FTR) shows very attractive EPR spectroscopic properties for a manifold of applications. For most of its applications only one chemically reactive functional group is needed. The presence of three equally reactive carboxyl groups leads to FTR modifications through reactions which give statistical mixtures of 1-fold-, 2-fold-, and 3-fold-modified and unmodified FTR. To avoid the side effects of such a statistical reaction - limited yields and separation challenges - we took a route to FTR-type trityl radicals with scaffold assembly by addition of an aryllithium with one type of substituent to a diarylketone with another type of substituent. This gave the two FTR-type trityl radicals 1 and 2 which carry a combination of the chemically orthogonal groups, carboxyl and triisopropylsilylethynyl. Standard column chromatography was sufficient for product isolation on all stages, whereby polar tagging helped. The EPR spectroscopic properties of the trityl radicals 1 and 2 in ethanol were determined in X and W bands. Their g anisotropy and T1 and T2 relaxation times make them spin labels as good as the benchmark FTR. This paper discloses also details on the synthesis of building blocks used for FTR preparation and improved access to the bare FTR scaffold.

Synthesis, Characterization, and Nanoencapsulation of Tetrathiatriarylmethyl and Tetrachlorotriarylmethyl (Trityl) Radical Derivativesí-A Study to Advance Their Applicability as in Vivo EPR Oxygen Sensors

Tissue oxygenation plays an important role in the pathophysiology of various diseases and is often a marker of prognosis and therapeutic response. EPR (ESR) is a suitable noninvasive oximetry technique. However, to reliably deploy soluble EPR probes as oxygen sensors in complex biological systems, there is still a need to investigate and improve their specificity, sensitivity, and stability. We reproducibly synthesized various derivatives of tetrathiatriarylmethyl and tetrachlorotriarylmethyl (trityl) radicals. Hydrophilic radicals were investigated in aqueous solution mimicking physiological conditions by, e.g., variation of viscosity and ionic strength. Their specificity was satisfactory, but the oxygen sensitivity was low. To enhance the capability of trityl radicals as oxygen sensors, encapsulation into oily core nanocapsules was performed. Thus, different lipophilic triesters were prepared and characterized in oily solution employing oils typically used in drug formulations, i.e., middle-chain triglycerides and isopropyl myristate. Our screening identified the deuterated ethyl ester of D-TAM (radical 13) to be suitable. It had an extremely narrow single EPR line under anoxic conditions and excellent oxygen sensitivity. After encapsulation, it retained its oxygen responsiveness and was protected against reduction by ascorbic acid. These biocompatible and highly sensitive nanosensors offer great potential for future EPR oximetry applications in preclinical research.

Generation of trityl radicals by nucleophilic quenching of tris(2,3,5,6-tetrathiaaryl)methyl cations and practical and convenient large-scale synthesis of persistent tris(4-carboxy-2,3,5,6-tetrathiaaryl)methyl radical

Tris(2,3,5,6-tetrathiaaryl)methyl cations, which were generated from the corresponding triarylmethanols in the presence of strong acids, underwent reaction with nucleophiles to give trityl radicals, as the product of a one-electron reduction of the carbocation. Depending on the nature of the nucleophile, the only byproducts were either diamagnetic quinone methides or asymmetrical monosubstituted trityl radicals. Herein, we report a protocol for the large-scale synthesis of the Finland trityl, which has the advantage of high overall yield and reproducibility. Tris(2,3,5,6-tetrathiaaryl)methyl cations, which were generated from the corresponding triarylmethanols and strong acids, underwent reaction with nucleophiles to give trityl radicals. Depending on the nucleophile, the only byproducts were diamagnetic quinone methides or asymmetrical monosubstituted trityl radicals. A protocol for the large-scale synthesis of the Finland trityl is reported. Copyright