329-14-6

Basic information

• Product Name: 4-TRIFLUOROMETHYL THIOANISOLE
• Synonyms: 4-TRIFLUOROMETHYL THIOANISOLE
• CAS NO: 329-14-6
• Molecular Formula: C₈H₇F₃S
• Molecular Weight: 192.2013896
• Mol File: 329-14-6.mol

Chemical Properties

• Boiling Point: 197.394 °C at 760 mmHg
• Flash Point: 73.182 °C
• Appearance: /
• Density: 1.259 g/cm³
• Vapor Pressure: 0.534mmHg at 25°C
• Refractive Index: 1.493
• CAS DataBase Reference: 4-TRIFLUOROMETHYL THIOANISOLE(CAS DataBase Reference)
• NIST Chemistry Reference: 4-TRIFLUOROMETHYL THIOANISOLE(329-14-6)
• EPA Substance Registry System: 4-TRIFLUOROMETHYL THIOANISOLE(329-14-6)

Safety Data

• Hazardous Substances Data: 329-14-6(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
4-Trifluoromethyl Thioanisole is used as an intermediate in organic synthesis for the development of pharmaceutical drugs. Its unique structure and reactivity contribute to the creation of complex drug molecules, enhancing their efficacy and selectivity.
Used in Chemical Industry:
In the chemical industry, 4-Trifluoromethyl Thioanisole serves as a building block for the synthesis of various chemical compounds. Its trifluoromethyl group and sulfide functionality provide versatility in the design and synthesis of novel chemical entities with potential applications in different fields.

InChI:InChI=1/C8H7F3S/c1-12-7-4-2-6(3-5-7)8(9,10)11/h2-5H,1H3

Upstream product

• 825-83-2 4-trifluoromethylbenzenethiol 
• 74-88-4 methyl iodide 
• 110935-27-8 {CpFe(CO)2S(C₆H₄-p-CF₃)(CH₃)}I 
• 402-54-0 p-nitrobenzotrifluoride 
• 3908-55-2 Trimethyl(methylthio)silane 
• 98546-51-1 (4-thiomethoxyphenyl)boronic acid 
• 455-14-1 4-trifluoromethylphenylamine 
• 624-92-0 Dimethyldisulphide 
• 455-13-0 4-Iodobenzotrifluoride 
• 67-68-5 dimethyl sulfoxide 
• 5188-07-8 sodium thiomethoxide 
• 98-56-6 4-chlorobenzotrifluoride 
• 616-38-6 carbonic acid dimethyl ester 
• 25752-91-4 2-methyl-2-propyl 4-trifluoromethylphenyl sulfide 

Downstream Products

• 102582-93-4 <4-(trifluoromethyl)phenylthio>acetic acid 
• 1251954-94-5 S-methyl-S-[4-(trifluoromethyl)phenyl]-N-(trifluoromethanesulfonyl)sulfilimine 
• 478247-76-6 2-(4-(trifluoromethyl)phenyl)benzoxazole 
• 214360-65-3 4-trifluoromethylphenylboronic acid pinacol ester 

Relevant articles and documents

PROTEIN-MACROMOLECULE CONJUGATES AND METHODS OF USE THEREOF

The present disclosure provides protein-macromolecule conjugates, releasable linkers, and macromolecules, as defined herein. The disclosed conjugates provide unique properties that are based at least upon the properties of linker and number of linker-Macromolecule moieties. Also provided herein are a method of synthesis and use of conjugates in treating diseases and disorders.

Nickel-Catalyzed Reversible Functional Group Metathesis between Aryl Nitriles and Aryl Thioethers

We describe a new functional group metathesis between aryl nitriles and aryl thioethers. The catalytic system nickel/dcype is essential to achieve this fully reversible transformation in good to excellent yields. Furthermore, the cyanide- and thiol-free reaction shows high functional group tolerance and great efficiency for the late-stage derivatization of commercial molecules. Finally, synthetic applications demonstrate its versatility and utility in multistep synthesis.

Iridium-Catalyzed ortho-C-H Borylation of Thioanisole Derivatives Using Bipyridine-Type Ligand

A simple iridium catalytic system was developed that allows for a variety of 2-borylthioanisoles to be easily synthesized via ortho-selective C-H borylation of thioanisole derivatives. Once introduced, boryl and methylthio groups were converted by palladium-catalyzed transformations. Density functional theory calculations revealed that weak interactions, such as hydrogen bonding between the C-H bond of the SCH3 group and the oxygen atom of the boryl ligand, control the ortho-selectivity.

Copper-catalyzed and additive free decarboxylative trifluoromethylation of aromatic and heteroaromatic iodides

A copper-catalyzed decarboxylative trifluoromethylation of (hetero)aromatic iodides has been developed. Importantly, this new copper-catalyzed reaction operates in the absence of any ligands and metal additives. The protocol shows good functional group tolerance and is compatible with heteroaromatic systems. The reaction proved scalable to a 15 mmol scale with increased yield. Finally, late-stage installation of the trifluoromethyl functionality afforded the N-trifluoroacetamide variant of the antidepressant agent, Prozac, demonstrating the applicability of the developed method.

Cathodic C-H Trifluoromethylation of Arenes and Heteroarenes Enabled by an in Situ-Generated Triflyltriethylammonium Complex

While several trifluoromethylation reactions involving the electrochemical generation of CF3 radicals via anodic oxidation have been reported, the alternative cathodic, reductive radical generation has remained elusive. Herein, the first cathodic trifluoromethylation of arenes and heteroarenes is reported. The method is based on the electrochemical reduction of an unstable triflyltriethylammonium complex generated in situ from inexpensive triflyl chloride and triethylamine, which produces CF3 radicals that are trapped by the arenes on the cathode surface.

Reduction of CO2 with NaBH4/I2 for the Conversion of Thiophenols to Aryl Methyl Sulfides

We report a tandem reaction to realize reduction of carbon dioxide with thiophenols to generate aryl methyl sulfides under the NaBH4/I2 system with 18-crown-6 as the solvent. Thiophenols bearing electron-donating and electron-withdrawing groups are feasible in this reaction. Controlled experiment results indicate that 18-crown-6 plays a critical role in six-electron reduction of carbon dioxide.

Transition-Metal-Free Aryl-Heteroatom Bond Formation via C-S Bond Cleavage

Aryl-heteroatom bonds (C-Het) are almost ubiquitously present in chemical molecules. However, methods for diverse C-Het bond formations from a simple substrate are limited. Herein, we report a convenient and efficient C-S bond transformation of aryl sulfoniums to various C-Het bonds (C-O, C-S, C-Sn, C-Si, C-Se) in the absence of any transition-metal catalyst. These reactions proceeded in mild conditions with a wide substrate scope.

Cesium carbonate-promoted synthesis of aryl methyl sulfides using: S -methylisothiourea sulfate under transition-metal-free conditions

In the presence of cesium carbonate, an efficient synthesis of aryl methyl sulfides by the reactions of aryl halides with commercially available S-methylisothiourea sulfate is developed. This odourless and highly crystalline solid can be used as the subst

Palladium-Catalyzed Thiomethylation via a Three-Component Cross-Coupling Strategy

In this report, the combination of masked inorganic sulfur and dimethyl carbonate was designed to achieve thiomethylated cross coupling of aryl chlorides. Remarkably, this powerful strategy realized thiomethylation of nucleosides bearing unprotected ribose, chloride-containing pharmaceuticals with late-stage coupling, and herbicides possessing multiple heteroatoms and steric hindrance. Moreover, this protocol is practically amenable to multigram-scale synthesis with a lower catalysis loading and a higher yield.

Transalkylation of alkyl aryl sulfides with alkylating agents

The reaction of methyl iodide with tert-butylphenylsulfide in DMF leads to a transalkylation that produces methylphenylsulfide. This transalkylation reaction was further studied by 1H NMR spectroscopy. The polarity of the solvent, the electron density on the sulfur atom, and the strength of the alkylating agent (MeI, EtI, BuI, dimethyl sulfate, or dimethyl carbonate) played important roles in the reaction. The suggested mechanism of the reaction involves the formation of a dialkyl aryl sulfonium salt that subsequently eliminates the radical. This mechanism was supported by the observation of higher conversion rates for compounds with more branched alkyl groups on the sulfur atom, which may lead to the formation of more stable radicals.