141106-52-7

Usage

Uses

Used in Pharmaceutical Synthesis:
2,4-Difluorophenyl isothiocyanate is used as a key intermediate in the synthesis of various hydrazinecarbothioamides, which have potential applications in the pharmaceutical industry. These compounds are synthesized as follows:
1. N-(2,4-difluorophenyl)-2-(4-(phenylsulfonyl)benzoyl)hydrazinecarbothioamide
2. 2-(4-(4-chlorophenylsulfonyl)benzoyl)-N-(2,4-difluorophenyl)hydrazinecarbothioamide
3. 2-(4-(4-bromophenylsulfonyl)benzoyl)-N-(2,4-difluorophenyl)hydrazinecarbothioamide
These hydrazinecarbothioamides are synthesized for their potential use in the development of new drugs, particularly those targeting various diseases and conditions. The specific application reason for each synthesized compound may vary based on their unique properties and potential therapeutic effects.

Upstream product

• 75-15-0 carbon disulfide 
• 367-25-9 2,4-difluorophenylamine 
• 463-71-8 thiophosgene 
• 16420-13-6 N,N-Dimethylthiocarbamoyl chloride 

Downstream Products

• 354151-66-9 N-(2,4-Difluorophenyl)-N'-(3,4-difluorophenyl)thiourea 
• 371914-71-5 1-(3,4-difluoro-2-hydroxy-phenyl)-3-(2,4-difluoro-phenyl)-thiourea 
• 662146-10-3 1-(2,4-difluoro-phenyl)-3-(2-hydroxy-1,1-dimethyl-ethyl)-thiourea 
• 549521-45-1 1-(2,4-difluoro-phenyl)-3-(2,2-dimethyl-propyl)-2-thioxo-imidazolidine-4,5-dione 
• 549521-43-9 1-(2,4-difluoro-phenyl)-2-thioxo-3-(1,2,2-trimethyl-propyl)-imidazolidine-4,5-dione 
• 1152594-66-5 O-[2-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)ethyl] 2,4-difluorophenylthiocarbamate 
• 1152595-52-2 2-({[2-({[(2,4-difluorophenyl)amino]carbonothioyl}oxy)ethyl]amino}carbonyl)benzoic acid 
• 175277-76-6 1-(2,4-difluorophenyl)thiourea 
• 1242020-21-8 α-acetyl-2,4-dichloro-N-(2,4-difluorophenyl)benzene-ethanethioamide 

Relevant academic research and scientific papers

Synthesis and herbicidal activities of fluorine-containing 3-pyridylmethyl-2-phenyliminothiazolidine derivatives

A series of fluorine-containing 2-phenyliminothiazolidine derivatives were synthesized by a facile and mild method in high yields. The structures of all the title compounds were characterized by 1H NMR, IR and HRMS. The results of bioassay showed that most of target compounds exhibited efficient herbicidal activities against Echinochloa crusgalli, Sorghum vulgare, Digitaria sanguinalis, Eclipta prostrasta, Cucumis sativus and Brassica campestris at 50 mg L-1.

Microwave mediated synthesis of 2-aminooxazoles

A microwave mediated synthesis of 2-aminooxazoles at 150 °C was developed, providing products with a variety of functional groups. The reaction takes 5 min and provides product with a simple precipitation at moderate to good yields without the need for recrystallization or flash chromatography.

6-HETEROARYLOXY BENZIMIDAZOLES AND AZABENZIMIDAZOLES AS JAK2 INHIBITORS

The present disclosure provides 6-heteroaryloxy benzimidazole and azabenzimidazole compounds and compositions thereof useful for inhibiting JAK2.

Synthesis and nematicidal activity of piperazinedione derivatives based on the natural product Barettin

Nematodes are serious constraints of crop production worldwide. However, the traditional nematicides suffer from the side-effects, including environmental and human toxicity. Herein, more than 70 novel piperazinedione derivatives based on the natural product Barettin were synthesized and evaluated against the root-knot nematode Meloidogyne incognita (M. incognita). While most of synthesized compounds exhibited certain nematicidal activity at high concentration, the best one showed a nematicidal activity of 75% at 2.4 μmol/L.

Pyrazolopyrimidines: Potent Inhibitors Targeting the Capsid of Rhino- and Enteroviruses

There are currently no drugs available for the treatment of enterovirus (EV)-induced acute and chronic diseases such as the common cold, meningitis, encephalitis, pneumonia, and myocarditis with or without consecutive dilated cardiomyopathy. Here, we report the discovery and characterization of pyrazolopyrimidines, a well-tolerated and potent class of novel EV inhibitors. The compounds inhibit the replication of a broad spectrum of EV in vitro with IC50 values between 0.04 and 0.64 μM for viruses resistant to pleconaril, a known capsid-binding inhibitor, without affecting cytochrome P450 enzyme activity. Using virological and genetics methods, the viral capsid was identified as the target of the most promising, orally bioavailable compound 3-(4-trifluoromethylphenyl)amino-6-phenylpyrazolo[3,4-d]pyrimidine-4-amine (OBR-5-340). Its prophylactic as well as therapeutic application was proved for coxsackievirus B3-induced chronic myocarditis in mice. The favorable pharmacokinetic, toxicological, and pharmacodynamics profile in mice renders OBR-5-340 a highly promising drug candidate, and the regulatory nonclinical program is ongoing. Curing the common cold! A cluster of pyrazolopyrimidines with potent broad-spectrum activity against enteroviruses was discovered. Extensive structure-property relationship analyses led to the identification of 3-(4-trifluoromethyl-phenyl)amino-6-phenylpyrazolo[3,4-d]pyrimidine-4-amine, shown to be a blocker of the viral capsid protein, as a lead compound for drug development with favorable physicochemical, pharmacokinetic, and toxicological properties.

Environmentally benign one-pot synthesis of cyanamides from dithiocarbamates using I2 and H2O2

An environmentally benign reaction is devised for the synthesis of cyanamides from dithiocarbamate salts using iodine and H2O 2. Taylor & Francis Group, LLC.

Molecular iodine mediated preparation of isothiocyanates from dithiocarbamic acid salts

We have developed a general economical and environmentally benign method for the preparation of isothiocyanates from the corresponding dilhiocarbamic acid salts by using cheap and readily available reagent molecular iodine. This is perhaps the most efficient method reported so far for the synthesis of isothiocyanates. The reagent is easily available and nontoxic, and the precipitated sulfur can be removed easily; hence, this method is most suitable for large-scale synthesis. Wiley-VCH Verlag GmbH & Co. KGaA.

A one-pot preparation of cyanamide from dithiocarbamate using molecular iodine

An efficient one-pot method for the synthesis of cyanamides from dithiocarbamate salts via a double desulfurization strategy using molecular iodine is disclosed. Dithiocarbamates, by the action of iodine yield isothiocyanates in situ, which on treatment with aqueous NH3 give thioureas. The thioureas so generated undergo further oxidative desulfurization with I2 giving corresponding cyanamides in good yields. Environmental benignity, cost effectiveness and high yields are the important attributes of this one pot procedure. The Royal Society of Chemistry 2009.

Syntheses, structures and bioactivities of fluorine-containing phenylimino-thia(oxa)zolidine derivatives as agricultural bioregulators

From insight into the structure of trehazolin as trehalase inhibitor, six series of fluorine-containing phenylimino-thiazolidines (oxazolidines) derivatives were designed and prepared through a convenient synthesis of fluoroaryl isothiocyanate and a one-pot facile synthesis in high yield of fluorophenyl aminobenzoxazoles by cyclodesulfurization. The structures of the target compounds were confirmed with using IR, NMR, MS and elemental analysis. Their X-ray crystal analysis suggested that there were novel intermolecular (sp2CF?H3C) and intramolecular (sp 2CF?HN) hydrogen bonds between the fluorine atom on benzene ring and hydrogen atom of methyl group or amino group on five-membered heterocycle. Their fungicidal activities against Rhizoctonia solani and Pyricuraria oryzae at 100 ppm were determined. From insight into the structure of trehazolin as trehalase inhibitor, six series of fluorine-containing phenylimino-thiazolidines (oxazolidines) derivatives were designed and prepared through a convenient synthesis of fluoroaryl isothiocyanate and a one-pot facile synthesis in high yield of fluorophenyl aminobenzoxazoles by cyclodesulfurization. The structures of the target compounds were confirmed with using IR, NMR, MS and elemental analysis. Their X-ray crystal analysis suggested that there were novel intermolecular (sp2CF?H 3C) and intramolecular (sp2CF?HN) hydrogen bonds between the fluorine atom on benzene ring and hydrogen atom of methyl group or amino group on five-membered heterocycle. Their fungicidal activities against Rhizoctonia solani and Pyricuraria oryzae at 100 ppm were determined. fx1

Synthesis and quantitative structure - Activity relationships of fluorine-containing 4,4-dihydroxylmethyl-2-aryliminooxazo(thiazo)lidines as trehalase inhibitors

Five fluorine-containing 4,4-dihydroxylmethyl-2-aryliminooxazolidines and five 4,4-dihydroxylmethyl-2-aryliminothiazolidines were synthesized and evaluated for their inhibitory activity against trehalase in vitro. All these compounds were very readily synthesized compared with the natural trehalase inhibitors. They had moderate inhibitory activity toward trehalase, and showed larvicidal activity and inhibition action to insect flight. The steric parameters and semiempirical quantum parameters of these compounds were acquired by using the molecular modeling method and the PM3-SCF-MO method, respectively. A quantitative structure - activity relationship between half-inhibitory concentrations toward trehalase and the above parameters was established.