372-16-7

Basic information

• Product Name: 4-(Trifluoromethylthio)aniline
• Synonyms: 4-Trifluoromethylsulfanyl-phenylamine;4-Aminophenyl trifluoromethyl sulphide 96%;4-Aminophenyltrifluoromethylsulphide96%;4-(TRIFLUOROMETHYLTHIO)ANILINE 99%;4-[(Trifluoromethyl)thio]benzenamine;4-(Trifluoromethylthio)aniline,95%;4-Aminophenyl trifluoromethyl sulphi;4-Aminophenyl trifluoromethyl sulphide, 4-[(Trifluoromethyl)sulphanyl]aniline
• CAS NO: 372-16-7
• Molecular Formula: C₇H₆F₃NS
• Molecular Weight: 193.19
• EINECS: 206-744-4
• Product Categories: Organic Building Blocks;Sulfides/Disulfides;Sulfur Compounds
• Mol File: 372-16-7.mol
• Article Data: 12

Chemical Properties

• Boiling Point: 102-103 °C8 mm Hg(lit.)
• Flash Point: 224 °F
• Appearance: Clear colorless to yellow/Liquid
• Density: 1.351 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.788mmHg at 25°C
• Refractive Index: n20/D 1.528(lit.)
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• PKA: 2.79±0.10(Predicted)
• Water Solubility: insoluble
• BRN: 2208859
• CAS DataBase Reference: 4-(Trifluoromethylthio)aniline(CAS DataBase Reference)
• NIST Chemistry Reference: 4-(Trifluoromethylthio)aniline(372-16-7)
• EPA Substance Registry System: 4-(Trifluoromethylthio)aniline(372-16-7)

Safety Data

• Hazard Codes: Xn,T,Xi
• Statements: 20/21/22
• Safety Statements: 36-36/37
• RIDADR: UN2810
• WGK Germany: 3
• HazardClass: 6.1
• PackingGroup: III
• Hazardous Substances Data: 372-16-7(Hazardous Substances Data)

Usage

Chemical Properties

clear colorless to yellow liquid

General Description

4-(Trifluoromethylthio)aniline is a 4-substituted aniline derivative.

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

Upstream product

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

Downstream Products

• 64628-04-2 1-(2-Methyl-benzoyl)-3-(4-trifluoromethylsulfanyl-phenyl)-urea 
• 76635-47-7 N,N'-Bis<4-(trifluormethylthio)phenyl>-dichlormaleinsaeure-diamid 
• 326-45-4 SKA-19 
• 588-81-8 thioacetic acid-(4-trifluoromethylsulfanyl-anilide) 
• 1423020-12-5 3-bromo-1-(3-chloropyridin-2-yl)-N-(2-oxo-2-((4-((trifluoromethyl)thio)phenyl)amino)ethyl)-1H-pyrazole-5-carboxamide 
• 183946-05-6 2-Cyano-N-(4-trifluoromethylsulfanyl-phenyl)-acetamide 
• 456-56-4 phenyl trifluoromethylsulfide 
• 55225-45-1 4-(2-chloro-1,1,2-trifluoroethoxy)-4'-(trifluoromethylthio)carbanilide 
• 55225-85-9 4,4-sulfonylbis(4'-(trifluoromethylthio)carbanilide) 
• 55225-81-5 4-(4-acetamidophenylsulfonyl)-4'-(trifluoromethylthio)carbanilide 
• 55225-80-4 4-(4-nitrophenylsulfonyl)-4'-(trifluoromethylthio)carbanilide 
• 55266-56-3 4-(4-(isopropylideneamino)phenylsulfonyl)-4'-(trifluoromethylthio)carbanilide 
• 55225-79-1 4-(trifluoromethylsulfonyl)-4'-(trifluoromethylthio)carbanilide 
• 55225-24-6 3-(trifluoromethyl)-4-ethoxy-4'-(trifluoromethylthio)carbanilide 

Relevant articles and documents

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.

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.

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.