76-84-6 Usage
Description
Triphenylmethanol, also known as Zidovudine EP Impurity D, is a triaryl methane derivative with a white powder or colorless trisolated crystals appearance. It is soluble in alcohol, ether, and benzene, and forms a dark yellow solution when dissolved in concentrated sulfuric acid. Triphenylmethanol is colorless when dissolved in glacial acetic acid, and it is insoluble in water and petroleum ether. It can be distilled at 360-380℃ without decomposition. Triphenylmethanol is known for its antiproliferative properties and is used in various applications across different industries.
Uses
1. Used in Pharmaceutical Industry:
Triphenylmethanol is used as an antiproliferative agent, particularly in the development of drugs that inhibit cell proliferation. Its ability to suppress the growth of cells makes it a valuable compound in the pharmaceutical sector for potential therapeutic applications.
2. Used in Research Laboratories:
Triphenylmethanol serves as a reagent in research laboratories, where it is utilized in various chemical reactions and experiments. Its versatility as a reagent makes it an essential component in scientific research.
3. Used in Dye Production:
As an intermediate in the production of commercially useful triarylmethane dyes, Triphenylmethanol plays a crucial role in the chemical industry. These dyes are widely used in various applications, including textiles, plastics, and printing inks.
4. Used in the Preparation of Triphenylmethane:
Triphenylmethanol is used in the synthesis of triphenylmethane, an important organic compound with various applications in the chemical and pharmaceutical industries.
5. Used in the Synthesis of Pyrylogen Reduction Product:
Triphenylmethanol is employed in the synthesis of the two-electron reduction product of pyrylogen, which is an essential step in the production of this compound.
6. Used in the Formation of Molecular Complexes:
Triphenylmethanol reacts with triphenylphosphine oxide to form a 1:1 molecular complex, which is significant in the field of supramolecular chemistry.
7. Used as a Clathrate Host:
Triphenylmethanol serves as a specific clathrate host for methanol and dimethyl sulphoxide, forming clathrate inclusion complexes. These complexes have potential applications in the storage and transport of gases, as well as in the development of new materials with unique properties.
Preparation
Triphenylmethanol synthesis: Triphenylmethanol was prepared by the action of benzene with carbon tetrachloride in the presence of Aluminum chloride, followed by acidification and hydrolysis.Triphenylmethanol can also be prepared by the reaction of phenylmagnesium bromide with methyl benzoate (instead of benzophenone).Synthesis of Triphenylmethanol
Reactions
The first one is the formation of the triphenylmethyl bromide from the reaction of triphenylmethanol with hydrobromic acid.
The second reaction is the formation of an ether from the reaction of triphenylmethanol with methanol in acidic conditions.
Synthesis Reference(s)
Organic Syntheses, Coll. Vol. 3, p. 839, 1955The Journal of Organic Chemistry, 57, p. 4555, 1992 DOI: 10.1021/jo00042a044
Purification Methods
Crystallise the carbinol from EtOH, MeOH, CCl4 (4mL/g), *benzene, hexane or pet ether (b 60-70o). Dry it at 90o. [Ohwada et al. J Am Chem Soc 108 3029 1986, Beilstein 6 IV 5014.]
Check Digit Verification of cas no
The CAS Registry Mumber 76-84-6 includes 5 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 2 digits, 7 and 6 respectively; the second part has 2 digits, 8 and 4 respectively.
Calculate Digit Verification of CAS Registry Number 76-84:
(4*7)+(3*6)+(2*8)+(1*4)=66
66 % 10 = 6
So 76-84-6 is a valid CAS Registry Number.
InChI:InChI=1/C19H16O/c20-19(16-10-4-1-5-11-16,17-12-6-2-7-13-17)18-14-8-3-9-15-18/h1-15,20H
76-84-6Relevant articles and documents
Wiig
, p. 4742,4743, 4748 (1930)
West et al.
, p. 6269,6271 (1960)
-
Morton,Stevens
, p. 2244,2246, 4028, 4030 (1931)
-
Metal-Free Access to (Spirocyclic)Tetrahydro-β-carbolines in Water Using an Ion-Pair as a Superacidic Precatalyst
Ji, Liang,Jia, Zhenhua,Liu, Xiaoxiao,Loh, Teck-Peng,Zhang, Ting,Zhang, Zhenguo
, p. 2052 - 2057 (2022/02/10)
The unprecedented triarylcarbonium ion-pair-catalyzed Pictet-Spengler reaction of tryptamines with aromatic aldehydes and cyclic ketones in water was disclosed. Under metal-free conditions, diverse tetrahydro-β-carbolines and spirocyclic tetrahydro-β-carb
Nonheme Diiron Oxygenase Mimic That Generates a Diferric-Peroxo Intermediate Capable of Catalytic Olefin Epoxidation and Alkane Hydroxylation including Cyclohexane
Kaizer, József,Oloo, Williamson N.,Que, Lawrence,Szávuly, Miklós
, (2021/12/27)
Herein are described substrate oxidations with H2O2 catalyzed by [FeII(IndH)(CH3CN)3](ClO4)2 [IndH = 1,3-bis(2′-pyridylimino)isoindoline], involving a spectroscopically characterized (μ-oxo)(μ-1,2-peroxo)diiron(III) intermediate (2) that is capable of olefin epoxidation and alkane hydroxylation including cyclohexane. Species 2 also converts ketones to lactones with a decay rate dependent on [ketone], suggesting direct nucleophilic attack of the substrate carbonyl group by the peroxo species. In contrast, peroxo decay is unaffected by the addition of olefins or alkanes, but the label from H218O is incorporated into the the epoxide and alcohol products, implicating a high-valent iron-oxo oxidant that derives from O-O bond cleavage of the peroxo intermediate. These results demonstrate an ambiphilic diferric-peroxo intermediate that mimics the range of oxidative reactivities associated with O2-activating nonheme diiron enzymes.
C-H Activation by RuCo3O4Oxo Cubanes: Effects of Oxyl Radical Character and Metal-Metal Cooperativity
Amtawong, Jaruwan,Balcells, David,Handford, Rex C.,Skjelstad, Bastian Bjerkem,Suslick, Benjamin A.,Tilley, T. Don
, p. 12108 - 12119 (2021/08/20)
High-valent multimetallic-oxo/oxyl species have been implicated as intermediates in oxidative catalysis involving proton-coupled electron transfer (PCET) reactions, but the reactive nature of these oxo species has hindered the development of an in-depth understanding of their mechanisms and multimetallic character. The mechanism of C-H oxidation by previously reported RuCo3O4 cubane complexes bearing a terminal RuV-oxo ligand, with significant oxyl radical character, was investigated. The rate-determining step involves H atom abstraction (HAA) from an organic substrate to generate a Ru-OH species and a carbon-centered radical. Radical intermediates are subsequently trapped by another equivalent of the terminal oxo to afford isolable radical-trapped cubane complexes. Density functional theory (DFT) reveals a barrierless radical combination step that is more favorable than an oxygen-rebound mechanism by 12.3 kcal mol-1. This HAA reactivity to generate organic products is influenced by steric congestion and the C-H bond dissociation energy of the substrate. Tuning the electronic properties of the cubane (i.e., spin density localized on terminal oxo, basicity, and redox potential) by varying the donor ability of ligands at the Co sites modulates C-H activations by the RuV-oxo fragment and enables construction of structure-activity relationships. These results reveal a mechanistic pathway for C-H activation by high-valent metal-oxo species with oxyl radical character and provide insights into cooperative effects of multimetallic centers in tuning PCET reactivity.