32062-69-4

Usage

Uses

Used in Pharmaceutical Research:
1-(4-bromophenyl)-3-phenylthiourea is used as a research compound for its potential anti-inflammatory and antiviral properties, making it a valuable tool in the development of new medications to combat inflammation and viral infections.
Used in Organic Synthesis:
In the field of organic chemistry, 1-(4-bromophenyl)-3-phenylthiourea is used as a synthetic building block and reagent in various chemical reactions, contributing to the creation of novel compounds with diverse applications.
Used in Chemical Reactions:
As a reagent, 1-(4-bromophenyl)-3-phenylthiourea is employed in chemical processes to facilitate specific transformations, enhancing the efficiency and selectivity of these reactions.
Overall, 1-(4-bromophenyl)-3-phenylthiourea is a multifaceted chemical compound with a broad spectrum of potential applications across different industries, including pharmaceuticals, organic synthesis, and chemical research.

Upstream product

• 62-53-3 aniline 
• 1985-12-2 4-Bromophenyl isothiocyanate 
• 106-40-1 4-bromo-aniline 
• 29647-72-1 o-phenyl (4-bromophenyl)carbamothioate 
• 103-72-0 phenyl isothiocyanate 
• 75-15-0 carbon disulfide 

Downstream Products

• 104672-90-4 [3-(4-bromo-phenyl)-thiazolidin-2-ylidene]-phenyl-amine 
• 755699-68-4 N-(4-bromo-phenyl)-S-methyl-N'-phenyl-isothiourea 
• 72544-85-5 (4-bromo-phenyl)-[4-(4-chloro-phenyl)-3-phenyl-3H-thiazol-2-ylidene]-amine 
• 53288-65-6 1-(4-bromophenyl)-3-phenylcarbodiimide 
• 1308273-00-8 N-(4-bromophenyl)-1-phenyl-1H-tetrazol-5-amine 
• 1308272-94-7 1-(4-bromophenyl)-N-phenyl-1H-tetrazol-5-amine 
• 36969-54-7 3-(4-bromo-phenyl)-2-phenylimino-thiazolidin-4-one 
• 6278-86-0 N₂-(4-bromophenyl)-1,3-benzothiazol-2-amine 
• 50871-89-1 4-(4-bromophenyl)-N-phenyl-4H-1,2,4-triazol-3-amine 
• 50871-88-0 N-(4-bromophenyl)-4-phenyl-4H-1,2,4-triazol-3-amine 
• 1017535-57-7 1-acetyl-1-(p-bromophenyl)-3-phenylurea 
• 80529-77-7 Cd(N-phenyl-N'-p-bromophenylthiourea)2(NCS)2 
• 72544-91-3 4-(4-chlorophenyl)-3-phenylthiazol-2(3H)-one 
• 13114-92-6 1-(4-bromophenyl)-3-phenyl-urea 

Relevant academic research and scientific papers

Nitroarenes as versatile building blocks for the synthesis of unsymmetrical urea derivatives and N-Arylmethyl-2-substituted benzimidazoles

In this contribution, a fast and simple method for the synthesis of unsymmetrical urea derivatives and N-arylmethyl-2-substituted benzimidazoles was developed starting from nitroarenes. The reaction of nitroarenes and phenyl isocyanate or phenyl isothiocyanate in tin (II) chloride dihydrate/choline chloride eutectic mixture afforded the expected urea and thiourea derivatives, while the reaction of different aldehydes with o-nitroaniline or 4-methoxy-2-nitroaniline shows a markedly high preference for the obtention of N-arylmethyl-2-substituted benzimidazoles over the 2-substituted analogues. This method offers a straightforward alternative to obtain the target compounds in good to excellent yields with short reaction times employing an operationally simple experimental set-up. Graphic abstract: [Figure not available: see fulltext.] A series of unsymmetrical urea and thiourea derivatives together with 1,2-disubstituted benzimidazoles are easily obtained in good yields starting from nitroarenes employing the eutectic mixture tin (II) chloride dihydrate/choline chloride as reductive reaction media.

Tunable NIR-II emitting silver chalcogenide quantum dots using thio/selenourea precursors: Preparation of an MRI/NIR-II multimodal imaging agent

Aqueous-stable, Cd- and Pb-free colloidal quantum dots with fluorescence properties in the second near-infrared region (NIR-II, 1000-1400) are highly desirable for non-invasive deep-tissue optical imaging and biosensing. The low band-gap semiconductor, silver chalcogenide, offers a non-toxic and stable alternative to existing Pd, As, Hg and Cd-based NIR-II colloidal quantum dots (QDs). We report facile access to NIR-II emission windows with Ag2X (X = S, Se) QDs using easy-to-prepare thio/selenourea precursors and their analogues. The aqueous phase transfer of these QDs with a high conservation of fluorescence quantum yield (retention up to ～90%) and colloidal stability is demonstrated. A bimodal NIR-II/MRI contrast agent with a tunable fluorescence and high T1 relaxivity of 408 mM-1 s-1 per QD (size ～ 2.2 nm) and 990 mM-1 s-1 per QD (size ～ 4.2 nm) has been prepared by grafting 50 and 120 monoaqua Gd(iii) complexes respectively to two differently sized Ag2S QDs. The size of the nanocrystals is crucial for tuning the Gd payload and the relaxivity.

Nickle Catalysis Enables Access to Thiazolidines from Thioureas via Oxidative Double Isocyanide Insertion Reactions

An efficient synthesis of thiazolidine-2,4,5-triimine derivatives was developed via Ni-catalyzed oxidative double isocyanide insertion to thioureas under air conditions, in which thioureas play three roles as a substrate, a ligand, and overcoming isocyanide polymerization. The reaction is featured by employing a low-cost and low loading Ni(acac)2 catalyst, without any additives, and high atom economy. This is the first example to directly apply a Ni(II) catalyst in oxidative double isocyanide insertion reactions.

Inhibition of adipogenesis by thiourea derivatives

Background: Obesity is one of the major health problems with inherent risk of type 2 diabetes, hypertension, CVDs, etc. Adipogenesis is a major contributor in the process of obesity. Inhibition of adipocytes differentiation is one of the key approaches to treat obesity. Objective: To discover the new inhibitors of adipogenesis as the treatment for obesity. Method: We describe here, the synthesis, and anti-adipogenic activity of thiourea derivatives 1-14. These derivatives were synthesized by the reactions of phenyl and pentafluorophenyl isothiocyanate with different aromatic amines. Pure compounds 1-14 were evaluated for their in vitro antiadipogenesis activity employing 3T3-L1 cells lines. Results: Compounds 1-3, 5-9, and 11-14 significantly inhibited the pre-adipocyte differentiation into adipocytes, which was measured by staining the cells, and through morphological examination. Compound 10 (1-(4"-Chlorophenyl)-3-(pentafluorophenyl)-thiourea) showed a potent inhibition of adipocyte differentiation with IC50 = 740.00 ± 2.36 nM, which was more potent than the standards, epigallocatechin gallate (IC50 = 16.73 ± 1.34 μM), and curcumin (IC50 = 18.62 ± 0.74 μM). All other compounds showed a moderate to weak anti-adipogenesis activity. Compounds 1- 14 were also evaluated for their cytotoxicity. Compounds 3, 10, and 14 showed some toxicity to the cancer cell lines, while compounds 2, 3, 10, 12, and 14 showed a moderate to weak cytotoxicity against the normal cell lines. Conclusion: All the compounds reported in this paper are known, except compound 11. They have been identified as new inhibitors of Adipogenesis. Adipogenesis is the process of adipocytes differentiation from pre-adipocytes. This extensively studied model of cell diff differentiation. Further synthetic modifications, and optimization of anti-adipogenic activity may lead to the development of anti-obesity agents.

Convenient synthesis of unsymmetrical N,N′-disubstituted thioureas in water

A simple and convenient two-step method has been developed and used to synthesise 25 (4 of which are novel) unsymmetrical N,N′-disubstituted thioureas in water. Alkylamines or variously substituted arylamines reacted smoothly with phenyl chlorothionoformate at room temperature to form thiocarbamates, which were then reacted with another alkyl- or arylamine in water at reflux to afford the unsymmetrical N,N′-disubstituted thioureas in good to excellent yields. Mild conditions, simple work-up, high yields as well as using water as solvent are the major advantages of the method.

Synthesis and in vitro urease inhibitory activity of N,N′- disubstituted thioureas

Thiourea derivatives (1-38) were synthesized and evaluated for their urease inhibition potential. The synthetic compounds showed a varying degree of in vitro urease inhibition with IC50 values 5.53 ± 0.02-91.50 ± 0.08 μM, most of which are superior to the standard thiourea (IC50 = 21.00 ± 0.11 μM). In order to ensure the mode of inhibition of these compounds, the kinetic study of the most active compounds has been carried out. Most of these inhibitors were found to be mixed-type of inhibitors, except compounds 13 and 30 which were competitive, while compound 19 was identified as non-competitive inhibitor with Ki values between 8.6 and 19.29 μM.

Synthesis and biological evaluation of halogenated 2-arylimino-3- arythiazolidine-4-ones containing benzoic acid fragments as antibacterial agents

A series of halogenated 2-arylimino-3-ary-thiazolidine-4-ones containing (5-furan-2-yl)-benzoic acid or (5-thiophene-2-yl)-benzoic acid fragments was synthesized, and evaluated in vitro for their antibacterial activity, antibiofilm activity, erythrocyte h

Tandem regioselective synthesis of tetrazoles and related heterocycles using iodine

A one-pot, tandem process has been developed for the synthesis of a library of tetrazoles from aryl isothiocyanates. Condensation of aryl isothiocyanates with ammonia, and aryl amines (R-NH2) provided mono, 1,3-disubstituted symmetrical and unsymmetrical thioureas, which on desulfurization with molecular iodine (I2) led to formation of the corresponding heterocumulene (cyanamides or carbodiimides). The in situ generated heterocumulene on subsequent treatment with sodium azide at room temperature gave corresponding tetrazoles. The product regioselectivity for unsymmetrical 1,3-disubstituted thioureas was found to be correlated with the basicities (pKa's) of the parent amines attached to the thiourea. Aryl-sec-alkyl unsymmetrical thioureas gave thioamido guanidino products rather than the 5-aminotetrazoles produced by HgCl2 mediation of the reaction. Bis-thioureas derived from aryl isothiocyanates and hydrazine gave thiadiazoles exclusively.

Synthesis, phytotoxic, cytotoxic, acetylcholinesterase and butrylcholinesterase activities of N,N-diaryl unsymmetrically substituted thioureas

Fourteen N,N-diaryl unsymmetrically substituted thioureas were synthesised and their cytotoxic (in vitro), phytotoxic (in vitro), acetylcholinesterase and butrylcholinesterase activities were determined. Thiourea 16 exhibited high, and 1 and 3 showed significant phytotoxic activity. Thioureas 1, 3, 4, 6 and 10 showed significant activity and 2, 6 and 7 indicated moderate cytotoxic activities. Compound 12 exhibited butrylcholinesterase activity higher than a standard reference.