372-16-7

Usage

Uses

Used in Pharmaceutical Industry:
4-(Trifluoromethylthio)aniline is used as a key intermediate in the synthesis of pharmaceutical compounds for its ability to impart specific biological activities and improve drug properties such as solubility, stability, and bioavailability.
Used in Agrochemical Industry:
In the agrochemical sector, 4-(Trifluoromethylthio)aniline serves as a building block for the development of novel agrochemicals, including insecticides, herbicides, and fungicides, due to its potential to enhance the effectiveness and selectivity of these compounds.
Used in Dye and Pigment Industry:
4-(Trifluoromethylthio)aniline is utilized as a precursor in the production of dyes and pigments, where its unique properties contribute to the color intensity, stability, and application range of the final products.
Used in Material Science:
4-(Trifluoromethylthio)aniline is employed in the development of advanced materials, such as polymers and coatings, where its chemical structure can influence properties like durability, resistance to environmental factors, and specific interactions with other materials.

InChI:InChI=1/C7H6F3NS/c8-7(9,10)12-6-3-1-5(11)2-4-6/h1-4H,11H2

Upstream product

• 100-32-3 di(p-nitrophenyl) disulfide 
• 2314-97-8 iodotrifluoromethane 
• 1193-02-8 4-aminotiophenol 
• 1314-15-4 platinum(IV) oxide 
• 403-66-7 p-nitrophenyl trifluoromethyl sulfide 
• 2926-29-6 Langlois reagent 
• 586-78-7 para-nitrophenyl bromide 
• 1045821-71-3 N-[(trifluoromethyl)sulfanyl]aniline 
• 1849-36-1 para-nitrobenzenethiol 
• 100-01-6 4-nitro-aniline 
• 713-66-6 4-nitrophenyl trichloromethylsulfide 
• 701-57-5 1-methylthio-4-nitro-benzene 

Downstream Products

• 333-47-1 1-bromo-4-(trifluoromethyl)thiobenzene 
• 372-15-6 1-iodo-4-(trifluoromethylsulfanyl)benzene 
• 64628-04-2 1-(2-Methyl-benzoyl)-3-(4-trifluoromethylsulfanyl-phenyl)-urea 
• 64627-98-1 N-(4-trifluoromethylthiophenyl)-N'-(2,6-difluorobenzoyl)-urea 
• 55225-73-5 4-(fluorosulfonyl)-4'-(trifluoromethylthio)carbanilide 
• 55225-61-1 4-(4-chlorophenoxy)-4'-(trifluoromethylthio)thiocarbanilide 
• 64627-99-2 1-(2-Fluoro-benzoyl)-3-(4-trifluoromethylsulfanyl-phenyl)-urea 
• 64628-05-3 1-(2-Bromo-benzoyl)-3-(4-trifluoromethylsulfanyl-phenyl)-urea 
• 326-45-4 SKA-19 
• 55266-54-1 N,N'-bis(4-trifluoromethylthiophenyl)urea 
• 55225-66-6 4-(4-methylphenoxycarbonyl)-4'-(trifluoromethylthio)carbanilide 
• 55225-24-6 3-(trifluoromethyl)-4-ethoxy-4'-(trifluoromethylthio)carbanilide 
• 55225-79-1 4-(trifluoromethylsulfonyl)-4'-(trifluoromethylthio)carbanilide 
• 55266-56-3 4-(4-(isopropylideneamino)phenylsulfonyl)-4'-(trifluoromethylthio)carbanilide 

Relevant academic research and scientific papers

A concise and convenient synthesis of 4-(trifluoromethylthio)aniline

4-(Trifluoromethylthio)aniline, a key agricultural intermediate, can be synthesized from 4-nitrobromobenzene. First 4-nitrothioanisole was obtained by the methylthiotriazine of 4-nitrobromobenzene with sodium salt of methyl mercaptan in the presence of phase-transfer catalyst in a 91.4 % yield; then 4-(trifuroromethylthio)nitrobenzene was produced through chlorination in a 83.7 % yield and fluorination in a 86.3 % yield; finally the hydrogenation in the presence of Pd/C can afford 4-(trifluoromethylthio)aniline with a 98 % yield.

Chalcogen OCF3 Isosteres Modulate Drug Properties without Introducing Inherent Liabilities

The synthesis of SCF3 as well as SeCF3 isosteres of two OCF3-containing drugs was achieved through visible light and copper-catalyzed processes. Herein, we show that chalcogen replacement modulates physicochemical and ADME properties without introducing intrinsic liabilities. The SCF3 and SeCF3 groups are more lipophilic than their oxygen counterpart; however, microsomal stability is unchanged, indicating that these molecular changes may be beneficial for in vivo half-life. Enabled by modern synthetic methods, we present the chalcogen-CF3 groups as potential key players for future fluorinated pharmaceuticals.

Enhancement of Benzothiazoles as Pteridine Reductase-1 Inhibitors for the Treatment of Trypanosomatidic Infections

2-Amino-benzo[d]thiazole was identified as a new scaffold for the development of improved pteridine reductase-1 (PTR1) inhibitors and anti-trypanosomatidic agents. Molecular docking and crystallography guided the design and synthesis of 42 new benzothiazoles. The compounds were assessed for Trypanosoma brucei and Leishmania major PTR1 inhibition and in vitro activity against T. brucei and amastigote Leishmania infantum. We identified several 2-amino-benzo[d]thiazoles with improved enzymatic activity (TbPTR1 IC50 = 0.35 μM; LmPTR1 IC50 = 1.9 μM) and low μM antiparasitic activity against T. brucei. The ten most active compounds against TbPTR1 were able to potentiate the antiparasitic activity of methotrexate when evaluated in combination against T. brucei, with a potentiating index between 1.2 and 2.7. The compound library was profiled for early ADME toxicity, and 2-amino-N-benzylbenzo[d]thiazole-6-carboxamide (4c) was finally identified as a novel potent, safe, and selective anti-trypanocydal agent (EC50 = 7.0 μM). Formulation of 4c with hydroxypropyl-β-cyclodextrin yielded good oral bioavailability, encouraging progression to in vivo studies.

Diversification of Trifluoromethylthiolation of Aromatic Molecules with Derivatives of Trifluoromethanesulfenamide

Trifluoromethylthiolation of aromatic compounds with different electrophilic reagents of the type ArNHSCF3 was studied in the presence of triflic acid as an activator. The effect of the reagent structure on the reactivity was studied with three different reagents: PhNHSCF3 (H/SCF3, 1a), 4-ClC6H4NHSCF3 (Cl/SCF3, 1b) and C6F5NHSCF3 (F5/SCF3, 1c). p-Chloro substituted reagent 1b was more stable than the unsubstituted 1a and was the most effective because it could not react by trifluoromethylthiolation of itself. This reaction was the most important side reaction of 1a. The pentafluoro derivative 1c was less reactive. Solvent played an important role in the transformation and, depending on the substrate, dichloromethane, hexane or trifluoroacetic acid gave the best yield of various trifluoromethylthiolated aromatic molecules (63–98 %).

Trifluoromethylation of thiophenols and thiols with sodium trifluoromethanesulfinate and iodine pentoxide

A selective and facile trifluoromethylation process for a wide range of thiophenols and thiols under metal free conditions has been developed using two simple and safe solids, sodium trifluoro-methanesulfinate and iodine pentoxide, via the radical process.

A mild and fast photocatalytic trifluoromethylation of thiols in batch and continuous-flow

S-CF3 bonds are important structural motifs in various pharmaceutical and agrochemical compounds. However, their preparation remains a major challenge in synthetic organic chemistry. Here, we report the development of a mild and fast photocatalytic trifluoromethylation of thiols. The combination of commercially available Ru(bpy)3Cl2, visible light and inexpensive CF3I gas proved to be an efficient method for the direct trifluoromethylation of thiols. The protocol is demonstrated on a wide range of aromatic, hetero-aromatic and aliphatic substrates in both batch and continuous microflow (32 examples, 52-98% yield). Process intensification through continuous microflow application resulted in a 15-fold increase in production rate (0.25 mmol min-1) due to improved gas-liquid mass transfer, enhanced irradiation as well as convenient handling of the gaseous CF3 source. Furthermore, the efficiency of the flow process allowed to reduce the amount of CF3I (1.1 equivalent) to reach full conversion. This journal is

Selective oxidation and chlorination of trifluoromethylsulfide using trichloroisocyanuric acid in ionic liquid

A route to chemoselective oxidation and chlorination of aryltrifluoromethylsulfide using trichloroisocyanuric acid (TCCA) in ionic liquid, an efficiently O-methylation reaction and a reduction of nitro- to amido- in excellent yields have been developed.

Substituted arylpyrazoles

This invention relates to a range of 1-aryl-4-cyclopropylpyrazoles in which there is at least one fluorine attached to the cyclopropyl ring, to compositions comprising such compounds, processes to their synthesis and their use as parasiticides.

5-HT2A receptor inverse agonists

Disclosed herein is a new class of pyrazole compounds which act at the 5HT2A receptors.

Small molecule modulators of non-endogenous, constitutively activated human serotonin receptors

Disclosed herein are non-endogenous, constitutively activated forms of the human 5-HT2A and human 5-HT2C receptors and uses of such receptors to screen candidate compounds. Further disclosed herein are candidate compounds identified by the screening method which act at the 5HT2A receptors. Yet further disclosed is a new class of compounds which act at the 5HT2A receptors.