1736-71-6

Basic information

• Product Name: 2-(Trifluoromethyl)phenylthiourea
• Synonyms: 2-(TRIFLUOROMETHYL)PHENYLTHIOUREA;1-[2-(TRIFLUOROMETHYL)PHENYL]-2-THIOUREA;6-TRIFLUOROMETHYL-3-PYRIDYLMETHANOL;6-TRIFLUOROMETHYL-3-PYRIDINEMETHANOL;RARECHEM AL BD 1231;[2-(trifluoromethyl)phenyl]-thioure;o-(trifluoromethyl)phenylthiourea;3-Hydroxy-6-(trifluoromethyl) pyridine
• CAS NO: 1736-71-6
• Molecular Formula: C₈H₇F₃N₂S
• Molecular Weight: 221.22
• EINECS: 217-084-1
• Product Categories: Heterocyclic Series;Pyridines
• Mol File: 1736-71-6.mol

Chemical Properties

• Melting Point: 163-165°C
• Boiling Point: 100-102°C/1mm
• Flash Point: 117.297 °C
• Appearance: /
• Density: 1.458 g/cm³
• Vapor Pressure: 0.056mmHg at 25°C
• Refractive Index: 1.462
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• BRN: 2695476
• CAS DataBase Reference: 2-(Trifluoromethyl)phenylthiourea(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(Trifluoromethyl)phenylthiourea(1736-71-6)
• EPA Substance Registry System: 2-(Trifluoromethyl)phenylthiourea(1736-71-6)

Safety Data

• Hazard Codes: T,Xi
• Statements: 25-37/38-41-43
• Safety Statements: 26-36/37/39-45
• RIDADR: UN 2810 6.1/PG 3
• WGK Germany: 3
• TSCA: Yes
• HazardClass: 6.1
• PackingGroup: III
• Hazardous Substances Data: 1736-71-6(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
2-(Trifluoromethyl)phenylthiourea is used as a reagent for the preparation of heterocyclic compounds, which are important in the development of pharmaceuticals and agrochemicals. Its unique trifluoromethyl group contributes to the reactivity and selectivity of the reactions, making it a valuable building block in organic synthesis.
Used in Medicinal Chemistry Research:
2-(Trifluoromethyl)phenylthiourea exhibits inhibitory activity against various enzymes and possesses bioactivities, making it a promising candidate for drug discovery. Its ability to modulate biological targets and pathways can lead to the development of new therapeutic agents.
Used in Pharmaceutical Applications:
As a precursor for the synthesis of complex organic molecules, 2-(Trifluoromethyl)phenylthiourea has potential pharmaceutical applications. Its derivatives may exhibit therapeutic properties, and further research can lead to the discovery of novel drugs with improved efficacy and safety profiles.
Used in Academic and Industrial Research Settings:
2-(Trifluoromethyl)phenylthiourea is a versatile chemical reagent that finds applications in both academic and industrial research. Its unique properties and potential applications make it an important tool for chemists and researchers working in various fields, including organic synthesis, medicinal chemistry, and drug discovery.
However, it is important to handle 2-(Trifluoromethyl)phenylthiourea with caution due to its potential toxic and irritant properties. Proper safety measures should be taken to minimize risks during its use in research and development.

InChI:InChI=1/C7H6F3NO/c8-7(9,10)6-2-1-5(4-12)3-11-6/h1-3,12H,4H2

Upstream product

• 88-17-5 2-(trifluoromethyl)benzenamine 
• 63494-72-4 N-((2-(trifluoromethyl)phenyl)carbamothioyl)benzamide 
• 1147550-11-5 ammonium thiocyanate 
• 17356-08-0 thiourea 
• 1743-86-8 2-(trifluoromethyl)phenyl isothiocyanate 

Downstream Products

• 1743-86-8 2-(trifluoromethyl)phenyl isothiocyanate 
• 57513-63-0 N-(2-trifluormethylphenyl)-S-methylisothiourea 
• 60388-36-5 4-(trifluoromethyl)benzo[d]thiazol-2-amine 
• 89070-00-8 N-(2-trifluoromethylphenyl)-S-ethylisothiourea 
• 35160-11-3 N-(2-(trifluoromethyl)phenyl)-4,5-dihydrothiazol-2-amine 
• 701277-32-9 1-(2-trifluoromethylphenyl)-5-(2-trifluoromethylphenyl)-2-thioxo hexahydro-1,3,5-triazine 
• 82636-24-6 2-Methylsulfanyl-6-oxo-1-(2-trifluoromethyl-phenyl)-1,6-dihydro-pyrimidine-5-carboxylic acid ethyl ester 
• 82635-96-9 2-[2-Methyl-3-(2-trifluoromethyl-phenyl)-isothioureidomethylene]-malonic acid diethyl ester 
• 1959-06-4 N_.N'-Bis-(2-trifluormethyl-phenyl)-thioharnstoff 
• 1744-41-8 1-Guanyl-4-<2-trifluormethyl-phenyl>-thiosemicarbazid 
• 674290-09-6 ethyl 4-(4-cyanophenyl)-6-methyl-2-thioxo-1-[3-(trifluoromethyl)phenyl]-1,2,3,4-tetrahydro-5-pyrimidinecarboxylate 

Relevant articles and documents

Discovery of Novel Thiazol-2-Amines and Their Analogues as Bioactive Molecules: Design, Synthesis, Docking and Biological Evaluation

A simple and highly efficient procedure for the synthesis of novel thiazol-2-amines, via Mannich reaction with secondary amines, is described. The newly synthesized derivatives 8(a-e) and 9(a-e) were characterized by 1 H NMR, 13 C NMR, IR, Mass spectroscopy and elemental analysis. All the derivatives were evaluated for their in-vitro anti-microbial activity against a panel of pathogenic strains of bacteria and fungi. The SAR showed that the secondary amines had a significant impact on the in-vitro antimicrobial activity of this class of agents. The most potent analogue N-((1H-benzo[d]imidazol-1-yl)methyl)-N-(2(trifluoromethyl)phenyl)-4,5-dihydrothiazol-2-amine (8c) showed excellent inhibition with MIC (zoi) 6.25 (22.5), 25 (21.5) and 25 (18) μg/mL against E. coli, S. typhi and P. aeruginosa respectively as compared to the standard drug. Molecular docking results suggest that compound exhibited inhibitory activity by binding of the title compound within the active sites of the inhibiting Enoyl ACP reductase, Lipid A, Pyridoxal kinase and type I DHQase enzymes. The compound exhibited promising anti-microbial activity which can be further explored as potential lead for the development of cheaper, safe, effective and potent drugs against resistant microbial parasites.

Search for the Active Ingredients from a 2-Aminothiazole DMSO Stock Solution with Antimalarial Activity

Chemical decomposition of DMSO stock solutions is a common incident that can mislead biological screening campaigns. Here, we share our case study of 2-aminothiazole 1, originating from an antimalarial class that undergoes chemical decomposition in DMSO at room temperature. As previously measured biological activities observed against Plasmodium falciparum NF54 and for the target enzyme PfIspE were not reproducible for a fresh batch, we tackled the challenge to understand where the activity originated from. Solvent- and temperature-dependent studies using HRMS and NMR spectroscopy to monitor the decomposition led to the isolation and in vitro evaluation of several fractions against PfIspE. After four days of decomposition, we successfully isolated the oxygenated and dimerised compounds using SFC purification and correlated the observed activities to them. Due to the unstable nature of the two isolates, it is likely that they undergo further decomposition contributing to the overall instability of the compound.

4-PHENYL-N-(PHENYL)THIAZOL-2-AMINE DERIVATIVES AND RELATED COMPOUNDS AS ARYL HYDROCARBON RECEPTOR (AHR) AGONISTS FOR THE TREATMENT OF E.G. ANGIOGENESIS IMPLICATED OR INFLAMMATORY DISORDERS

4-phenyl-N-(phenyl)thiazol-2-amine and 4-(pyridin-3-yl)-N-( phenyl) thiazol-2-amine derivatives and the corresponding thiadiazole, thiophene, oxazole, oxadiazole, imidazole and triazole derivatives and related compounds as aryl hydrocarbon receptor (AHR) agonists for the treatment of angiogenesis implicated disorders, such as e.g. retinopathy, psoriasis, rheumatoid arthritis, obesity and cancer, or inflammatory disorders.

Green and efficient synthesis of thioureas, ureas, primary: O -thiocarbamates, and carbamates in deep eutectic solvent/catalyst systems using thiourea and urea

An efficient and general catalysis process was developed for the direct preparation of various primary O-thiocarbamates/carbamates as well as monosubstituted thioureas/ureas by using thiourea/urea as biocompatible thiocarbonyl (carbonyl) sources. This procedure used choline chloride/tin(ii) chloride [ChCl][SnCl2]2 with a dual role as a green catalyst and reaction medium to afford the desired products in moderate to excellent yields. Moreover, the DES can be easily recovered and reused for seven cycles with no significant loss in its activity. Besides, the method shows very good performance for synthesizing the desired products on a large scale.

Synergism of fused bicyclic 2-aminothiazolyl compounds with polymyxin B against: Klebsiella pneumoniae

A series of fused bicyclic 2-aminothiazolyl compounds were synthesized and evaluated for their synergistic effects with polymyxin B (PB) against Klebsiella pneumoniae (SIPI-KPN-1712). Some of the synthesized compounds exhibited synergistic activity. When 4 μg ml-1 compound B1 was combined with PB, it showed potent antibacterial activity, achieving 64-fold reduction of the MIC of PB. Furthermore, compound B1 showed prominent synergistic efficacy in both concentration gradient and time-kill curves in vitro. In addition, B1 combined with PB also exhibited synergistic and partial synergistic effect against E. coli (ATCC25922 and its clinical isolates), Acinetobacter baumannii (ATCC19606 and its clinical isolates), and Pseudomonas aeruginosa (Pae-1399).

Structure-activity relationships of 2-aminothiazoles effective against Mycobacterium tuberculosis

A series of 2-aminothiazoles was synthesized based on a HTS scaffold from a whole-cell screen against Mycobacterium tuberculosis (Mtb). The SAR shows the central thiazole moiety and the 2-pyridyl moiety at C-4 of the thiazole are intolerant to modification. However, the N-2 position of the aminothiazole exhibits high flexibility and we successfully improved the antitubercular activity of the initial hit by more than 128-fold through introduction of substituted benzoyl groups at this position. N-(3-Chlorobenzoyl)-4-(2-pyridinyl) -1,3-thiazol-2-amine (55) emerged as one of the most promising analogues with a MIC of 0.024 μM or 0.008 μg/mL in 7H9 media and therapeutic index of nearly ～300. However, 55 is rapidly metabolized by human liver microsomes (t1/2 = 28 min) with metabolism occurring at the invariant aminothiazole moiety and Mtb develops spontaneous low-level resistance with a frequency of ～10-5.

Synthesis and biological evaluation of substituted 4-arylthiazol-2-amino derivatives as potent growth inhibitors of replicating Mycobacterium tuberculosis H37RV

In search of potential therapeutics for tuberculosis, we describe herein synthesis and biological evaluation of some substituted 4-arylthiazol-2-amino derivatives as modified analogues of the antiprotozoal drug Nitazoxanide (NTZ), which has recently been reported as potent inhibitor of Mtb H37Rv (Mtb MIC = 52.12 μM) with an excellent ability to evade resistance. Among the synthesized derivatives, the two compounds 7a (MIC = 15.28 μM) and 7c (MIC = 17.03 μM) have exhibited about three times better Mtb growth inhibitory activity over NTZ and are free from any cytotoxicity (Vero CC50 of 244 and 300 μM respectively). These two compounds represent promising leads for further optimization.

Synthesis and antioxidant activity of quinolinobenzothiazinones

A new series of structurally diverse quinolinobenzothiazinones has been synthesized with the annulation of heterocyclic structural pharmacophores. The synthesized quinolinobenzothiazinones have been evaluated for their antioxidant (LPO & GSH) and radical scavenging activities (DPPH and ABTS assays).

Design, synthesis, cytoselective toxicity, structure-activity relationships, and pharmacophore of thiazolidinone derivatives targeting drug-resistant lung cancer cells

Ten cytoselective compounds have been identified from 372 thiazolidinone analogues by applying iterative library approaches. These compounds selectively killed both non-small cell lung cancer cell line H460 and its paclitaxel-resistant variant H460taxR at an IC50 between 0.21 and 2.93 μM while showing much less toxicity to normal human fibroblasts at concentrations up to 195 μM. Structure-activity relationship studies revealed that (1) the nitrogen atom on the 4-thiazolidinone ring (ring B in Figure 1) cannot be substituted, (2) several substitutions on ring A are tolerated at various positions, and (3) the substitution on ring C is restricted to the -NMe2 group at the 4-position. A pharmacophore derived from active molecules suggested that two hydrogen bond acceptors and three hydrophobic regions were common features. Activities against P-gp-overexpressing and paclitaxel-resistant cell line H460taxR and modeling using a previously validated P-gp substrate pharmacophore suggested that active compounds were not likely P-gp substrates.