1060-92-0

Usage

Uses

Used in Chemical Catalysis:
1,3-Bis[3,5-bis(trifluoromethyl)phenyl]thiourea is used as a thiourea catalyst for the activation of various chemical groups such as carbonyls, nitroolefins, and imines. Its ability to act as a hydrogen-bond donor makes it a versatile and efficient catalyst in a range of organic reactions.
Used in Green Chemistry:
1,3-Bis[3,5-bis(trifluoromethyl)phenyl]thiourea is utilized in the development of greener alternative products, aligning with one or more of The 12 Principles of Greener Chemistry. Its enhanced catalytic efficiency contributes to reducing waste, decreasing toxicity, and improving the overall sustainability of chemical processes.

InChI:InChI=1/C17H8F12N2S/c18-14(19,20)7-1-8(15(21,22)23)4-11(3-7)30-13(32)31-12-5-9(16(24,25)26)2-10(6-12)17(27,28)29/h1-6H,(H2,30,31,32)

Upstream product

• 23165-29-9 3,5-bistrifluoromethylphenylisothiocyanate 
• 328-74-5 3,5-Bis-(trifluoromethyl)aniline 
• 463-71-8 thiophosgene 
• 1298088-82-0 C₂₉H₁₆F₁₂N₂SSi 
• 1298088-80-8 C₁₇H₆Cl₂F₁₂N₂SSi 
• 6160-65-2 1,1'-Thiocarbonyldiimidazole 

Downstream Products

• 1298088-82-0 C₂₉H₁₆F₁₂N₂SSi 
• 1298088-80-8 C₁₇H₆Cl₂F₁₂N₂SSi 
• 1404310-23-1 C₁₇H₈F₁₂N₂S*C₅H₈O₂ 
• 1404310-27-5 C₁₇H₈F₁₂N₂S*C₆H₁₀O 
• 61474-61-1 methyl 2,3,4-tri-O-benzyl-6-O-(2,3,4,6-tetra-O-benzyl-D-glucopyranosyl)-α-D-glucopyranoside 

Relevant academic research and scientific papers

Organocatalytic Claisen rearrangement: Theory and experiment

(Chemical Equation Presented) A combined computational and experimental study on the Claisen rearrangement of a 2-alkoxycarbonyl-substituted allyl vinyl ether in the presence of thioureas as potential noncovalent organocatalysts has been performed. DFT ca

Influence of Anion-Binding Schreiner's Thiourea on DMAP Salts: Synergistic Catalysis toward the Stereoselective Dehydrative Glycosylation from 2-Deoxyhemiacetals

Amines are used as additives to facilitate or increase the host-guest chemistry between the thiourea and the anions of Bronsted acids. However, we here demonstrate, for the first time, the synergistic effect of the combination of DMAP/HCl/Schreiner's thio

Organophotocatalysis: Insights into the Mechanistic Aspects of Thiourea-Mediated Intermolecular [2+2]Photocycloadditions

Mechanistic investigations of the intermolecular [2+2] photocycloaddition of coumarin with tetramethylethylene mediated by thiourea catalysts reveal that the reaction is enabled by a combination of minimized aggregation, enhanced intersystem crossing, and

Supramolecular relay-control of organocatalysis with a hemithioindigo-based molecular motor

Integration of individual molecular components such as molecular motors or switches into larger meta-functional systems represents a current challenge at the forefront of molecular machine research. Here we present a modular supramolecular approach to relay the photoinduced geometry changes of a hemithioindigo based molecular motor into catalytic efficiency of a chemical reaction. Using the intrinsic chemical nature of the motor for recognition of different hydrogen-bonding organocatalysts a greater than 10-fold modulation in binding affinity is achieved upon photoisomerization. This change in affinity is then translated effectively into control of catalytic competence of the organocatalysts without direct interference by the motor. As an example the organocatalysed Michael addition reaction between nitrostyrene and 3-methoxy-dimethyl aniline was modulated in situ by visible light irradiation. Thus, dynamic and reversible remote control of catalytic processes by the switching capacity of a hemithioindigo molecular motor is established in a multicomponent chemical system. The high intrinsic modularity of this approach presents further advantages, e.g., for easy tailoring of conditions or facile exchange of catalysts and reactions. These results represent a first stepping stone into integrated chemical networks regulated by molecular machines in a fully dynamic way.

Hydrogen-Bond Catalysis of Imine Exchange in Dynamic Covalent Systems

The reversibility of imine bonds has been exploited to great effect in the field of dynamic covalent chemistry, with applications such as preparation of functional systems, dynamic materials, molecular machines, and covalent organic frameworks. However, acid catalysis is commonly needed for efficient equilibration of imine mixtures. Herein, it is demonstrated that hydrogen bond donors such as thioureas and squaramides can catalyze the equilibration of dynamic imine systems under unprecedentedly mild conditions. Catalysis occurs in a range of solvents and in the presence of many sensitive additives, showing moderate to good rate accelerations for both imine metathesis and transimination with amines, hydrazines, and hydroxylamines. Furthermore, the catalyst proved simple to immobilize, introducing both reusability and extended control of the equilibration process.

Synergetic Organocatalysis for Eliminating Epimerization in Ring-Opening Polymerizations Enables Synthesis of Stereoregular Isotactic Polyester

Ring-opening polymerization of O-carboxyanhydrides (OCAs) can furnish polyesters with a diversity of functional groups that are traditionally hard to harvest by polymerization of lactones. Typical ring-opening catalysts are subject to unavoidable racemization of most OCA monomers, which hampers the synthesis of highly isotactic crystalline polymers. Here, we describe an effective bifunctional single-molecule organocatalysis for selective ring-opening polymerization of OCAs without epimerization. The close vicinity of both activating groups in the same molecule engenders an amplified synergetic effect and thus allows for the use of mild bases, thereby leading to minimal epimerization for polymerization. Ring-opening polymerization of manOCA monomer (OCA from mandelic acid) mediated by the bifunctional single-molecule organocatalyst yields highly isotactic poly(mandelic acid) (PMA) with controlled molecular weights (up to 19.8 kg mol-1). Mixing of the two enantiomers of PMA generates the first example of a crystalline stereocomplex in this area, which displayed distinct Tm values around 150 °C. Remarkably, the bifunctional catalysts are moisture-stable, recyclable, and easy to use, allowing sustainable and scalable synthesis of a stereoregular functional polyester.

Mechanism-Based Condition Screening for Sustainable Catalysis in Single-Electron Steps by Cyclic Voltammetry

A cyclic-voltammetry-based screening method for Cp2TiX-catalyzed reactions is introduced. Our mechanism-based approach enables the study of the influence of various additives on the electrochemically generated active catalyst Cp2TiX, which is in equilibrium with catalytically inactive [Cp2TiX2]?. Thioureas and ureas are most efficient in the generation of Cp2TiX in THF. Knowing the precise position of the equilibrium between Cp2TiX and [Cp2TiX2]? allowed us to identify reaction conditions for the bulk electrolysis of Cp2TiX2 complexes and for Cp2TiX-catayzed radical arylations without having to carry out the reactions. Our time- and resource-efficient approach is of general interest for the design of catalytic reactions that proceed in single-electron steps.

Stereoselective Koenigs–Knorr Glycosylation Catalyzed by Urea

A stereoselective Koenigs–Knorr glycosylation reaction under the catalysis of urea is described. This method is characterized by urea-mediated hydrogen-bond activation and subsequent glycosylation with glycosyl chlorides or bromides. Excellent yields and high anomeric selectivity can be achieved in most cases. Moreover, the low α-stereoselectivity of glycosylations observed when using perbenzylated glucosyl donors can be greatly improved by the addition of tri-(2,4,6-trimethoxyphenyl)phosphine (TTMPP).

Stereoselective glycosylation of 2-nitrogalactals catalyzed by a bifunctional organocatalyst

The use of a bifunctional cinchona/thiourea organocatalyst for the direct and α-stereoselective glycosylation of 2-nitrogalactals is demonstrated for the first time. The conditions are mild, practical, and applicable to a wide range of glycoside acceptors with products being isolated in good to excellent yields. The method is exemplified in the synthesis of mucin type Core 6 and 7 glycopeptides.

Application of "hydrogen bonding interaction" in new drug development: Design, synthesis, antiviral activity, and sars of thiourea derivatives

A series of simple thiourea derivatives were designed based on the structure of natural product harmine and lead compound and synthesized from amines in one step. The antiviral activity of these thiourea derivatives was evaluated. Most of them exhibited significantly higher anti-TMV activity than commercial plant virucides ribavirin, harmine, and lead compound. The hydrogen bond was found to be important but not the more the better. The optimal compound (R,R)-20 showed the best anti-TMV activity in vitro and in vivo (in vitro activity, 75%/500 a??g/mL and 39%/100 a??g/mL; inactivation activity, 71%/500 a??g/mL and 35%/100 a??g/mL; curative activity, 73%/500 a??g/mL and 37%/100 a??g/mL; protection activity, 69%/500 a??g/mL and 33%/100 a??g/mL), which is significantly higher than that of Ningnanmycin. The systematic study provides strong evidence that these simple thiourea derivatives could become potential TMV inhibitors.