2059-75-8

Usage

Appearance

White to off-white crystalline solid

Solubility

Insoluble in water

Uses

a. Intermediate for the synthesis of pharmaceuticals and agrochemicals

Biological activity

Potential antifungal and antiparasitic properties

Research applications

Reagent for the determination of trace amounts of nickel and other metals in various samples

Hazard classification

Classified as a hazardous substance

Safety measures

Should be used in a controlled laboratory setting with appropriate safety measures

Upstream product

• 75-15-0 carbon disulfide 
• 106-40-1 4-bromo-aniline 
• 463-71-8 thiophosgene 
• 1985-12-2 4-Bromophenyl isothiocyanate 
• 4314-19-6 bis(1H-benzo[d][1,2,3]triazol-1-yl)methanethione 
• 333-20-0 potassium thioacyanate 
• 624-19-1 4-bromoaniline hydrochloride 
• 93253-29-3 2-deoxy-2-(ethylamino)-L-mannose hydrochlorid 

Downstream Products

• 726-41-0 bis(p-bromophenyl)carbodiimide 
• 75104-95-9 (6-bromo-benzothiazol-2-yl)-(4-bromo-phenyl)-amine 
• 51964-16-0 3-(4-bromophenyl)-2-(4-bromophenylimino)thiazolidin-4-one 
• 1985-12-2 4-Bromophenyl isothiocyanate 
• 35251-92-4 (4-bromo-phenyl)-[3-(4-bromo-phenyl)-6-nitro-3H-thiazolo[4,5-b]quinoxalin-2-ylidene]-amine 
• 23808-79-9 (4-bromo-phenyl)-[3-(4-bromo-phenyl)-4-(3,4-dimethoxy-phenyl)-3H-thiazol-2-ylidene]-amine 
• 20044-32-0 3-(4-bromo-phenyl)-2-(4-bromo-phenylimino)-4-methyl-2,3-dihydro-thiazole-5-carboxylic acid ethyl ester 
• 36220-48-1 (4-bromo-phenyl)-[3-(4-bromo-phenyl)-4-(4-methoxy-phenyl)-3H-thiazol-2-ylidene]-amine 
• 82686-83-7 (4-Bromo-phenyl)-[3-(4-bromo-phenyl)-4-isopropyl-3H-thiazol-(2Z)-ylidene]-amine 
• 116088-25-6 4-(N,N'-bis(4-bromophenyl)guanidino-2methyl-5-methylthio-2H-1,2,4-triazole-3(4H)-thione 
• 106038-57-7 4-(4-bromo-phenyl)-5-(4-bromo-phenylimino)-[1,2,4]dithiazolidin-3-one 
• 82686-67-7 (4-Bromo-phenyl)-[3-(4-bromo-phenyl)-5-isopropyl-4-methyl-3H-thiazol-(2Z)-ylidene]-amine 
• 78556-13-5 (4-Bromo-phenyl)-[3-(4-bromo-phenyl)-[1,3]thiazinan-(2Z)-ylidene]-amine 
• 134835-91-9 1-acetyl-1,3-di-(p-bromophenyl)urea 

Relevant academic research and scientific papers

Palladium catalyzed carbonylative annulation of the C(sp2)-H bond of N,1-diaryl-1H-tetrazol-5-amines and N,4-diaryl-4H-triazol-3-amines to quinazolinones

Pd(ii) catalyzed direct C-H carbonylative annulation of N,1-diaryl-1H-tetrazol-5-amines and N,4-diaryl-4H-1,2,4-triazol-3-amines gave the corresponding triazole and tetrazole fused quinazolinones in good yields. This methodology offers a convenient method for the synthesis of these important heterocyclic scaffolds in a highly atom economical process. On the mechanistic aspect weakly nucleophilic triazole and tetrazole moieties function as both directing as well as intramolecular nucleophiles. The catalytically active C-H activated intermediate dimeric Pd complex was isolated and characterized which on exposure to CO gas gave the corresponding tetrazole fused quinazolinone derivative. On the basis of isolation of the intermediate and observed kinetic isotope effects, a mechanism has been proposed for the C-H activated direct carbonylative annulation reaction.

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.

Novel non-peptidic small molecule inhibitors of secreted aspartic protease 2 (SAP2) for the treatment of resistant fungal infections

Targeting secreted aspartic protease 2 (SAP2), a kind of virulence factor, represents a new strategy for antifungal drug discovery. In this report, the first-generation of small molecule SAP2 inhibitors was rationally designed and optimized using a structure-based approach. In particular, inhibitor 23h was highly potent and selective and showed good antifungal potency for the treatment of resistant Candida albicans infections.

CERAMIDE GALACTOSYLTRANSFERASE INHIBITORS FOR THE TREATMENT OF DISEASE

Described herein are compounds, methods of making such compounds, pharmaceutical compositions and medicaments containing such compounds, and methods of using such compounds to treat or prevent diseases or disorders associated with the enzyme ceramide galactosyltransferase (CGT), such as, for example, lysosomal storage diseases. Examples of lysosomal storage diseases include, for example, Krabbe disease and Metachromatic Leukodystrophy.

Novel self-condensation of ammonium dithiocarbamates leading to symmetrical substituted thioureas

For the first time, the formation of symmetrical substituted thiourea analogues generated by the selfcondensation of trialkylammoniumdithiocarbamates is reported. The reactions occurred under mild conditions. The method allows the use of amines possessing a weak nucleophilic feature in good yields. The highlight of the study is a novel self-condensation mechanism based on dithiocarbamates as a basic compound in organic chemistry.

Formation of 1,4,2-Dithiazolidines or 1,3-Thiazetidines from 1,1-Dichloro-2-nitroethene and Phenylthiourea Derivatives

A method for preparation of 1,4,2-dithiazolidine or 1,3-thiazetidine heterocycles was developed by reactions of phenylthioureas with 1,1-dichloro-2-nitroethene. The solvent has a significant influence on the type of product formation. 1,4,2-Dithiazolidines were formed in the aprotic solvent chloroform, while in the protic solvent ethanol, 1,3-thiazetidines were the main products.

Naphthyridine derivatives as a model system for potential lithium-sulfur energy-storage applications

Naphthyridines have been identified as structural elements in sulfurized polyacrylonitrile, which is a common electrode material in lithium-sulfur batteries. Some dibenzonaphthyridine derivatives with a fused dithiolo moiety were prepared as model compounds for battery studies. These heterocyclic systems were prepared via the corresponding diphenyldicarbamide intermediate. Followed by naphthyridione formation, stepwise installation of the dithiolane subunit occurred in a straightforward manner. In the solid state, the heteroaromatic system is completely planar and was thoroughly characterized. Initial battery cycling tests indicated a potential use of such structural motifs in sulfur-lithium systems.

Trapping Reactive Intermediates by Mechanochemistry: Elusive Aryl N-Thiocarbamoylbenzotriazoles as Bench-Stable Reagents

Monitoring of mechanochemical thiocarbamoylation by in situ Raman spectroscopy revealed the formation of aryl N-thiocarbamoylbenzotriazoles, reactive intermediates deemed unisolable in solution. The first-time isolation and structural characterization of these elusive molecules demonstrates the ability of mechanochemistry to access otherwise unobtainable intermediates and offers a new range of masked isothiocyanate reagents.

Water promoted one pot three-component synthesis of tetrazoles

A one pot, three component synthesis of tetrazoles via thiourea has been accomplished in water. Water enhances the solubility of a higher number of components in the three component protocol thus promoting the reaction. The synthesis involves a chemoselective exocyclic reaction, regioselective electrocyclisation and a preferred conformational orientation of the tetrazole side chain which are rationalised based on the relative magnitude of Garbisch angle strain/allylic strains anticipated during the course of the reaction.

A simple and straightforward synthesis of phenyl isothiocyanates, symmetrical and unsymmetrical thioureas under ball milling

Promoted by KOH under ball milling, anilines were efficiently transformed into isothiocyanates (in presence of 5.0 equiv. CS2) or symmetrical thioureas (in presence of 1.0 equiv. CS2), without using any other harsh or toxic decomposition reagent. Some in situ generated isothiocyanates can directly "click" with other amines to afford unsymmetrical thioureas.