2740-88-7

Usage

Uses

Used in Pharmaceutical Industry:
4-Fluorobenzyl isothiocyanate is used as a key intermediate in the synthesis of new drugs, contributing to the development of pharmaceuticals with potential therapeutic applications.
Used in Organic Synthesis:
4-FLUOROBENZYL ISOTHIOCYANATE serves as a versatile building block in organic synthesis, enabling the creation of a wide range of chemical compounds for various applications.
Used in Agrochemical Production:
4-Fluorobenzyl isothiocyanate is also utilized in the production of agrochemicals, playing a role in the development of substances that can protect crops and enhance agricultural productivity.
Used in Laboratory Research:
Due to its reactivity and potential in chemical synthesis, 4-fluorobenzyl isothiocyanate is frequently used in laboratory research to explore new chemical reactions and synthesize novel compounds.

InChI:InChI=1/C8H6FNS/c9-8-3-1-7(2-4-8)5-10-6-11/h1-4H,5H2

Upstream product

• 140-75-0 para-fluorobenzylamine 
• 75-15-0 carbon disulfide 
• 32315-10-9 bis(trichloromethyl) carbonate 
• 2740-87-6 p-fluorobenzyl thiocyanate 
• 463-71-8 thiophosgene 

Downstream Products

• 1122-82-3 isothiocyanatocyclohexane 
• 897514-14-6 4-(3-(4-fluorobenzyl)thioureido)-N-(5-methylisoxazol-3-yl)benzenesulfonamide 
• 1352552-23-8 2-(4-dimethylaminophenyl)-4-(4-fluorobenzyl)-1,2,4-thiadiazolidine-3,5-dione 
• 1352552-22-7 2-(4-t-butylphenyl)-4-(4-fluorobenzyl)-1,2,4-thiadiazolidine-3,5-dione 
• 1055193-18-4 2-(3-methylphenyl)-4-(4-fluorobenzyl)-1,2,4-thiadiazolidine-3,5-dione 
• 1055193-25-3 2-(4-chlorophenyl)-4-(4-fluorobenzyl)-1,2,4-thiadiazolidine-3,5-dione 
• 1055193-29-7 2-phenyl-4-(4-fluorobenzyl)-1,2,4-thiadiazolidine-3,5-dione 
• 883050-24-6 4-[(4-fluorophenyl) methyl]-2-(4-methylphenyl)-1,2,4-thiadiazolidine-3,5-dione 
• 1055193-27-5 2-(4-methoxyphenyl)-4-(4-fluorobenzyl)-1,2,4-thiadiazolidine-3,5-dione 
• 1352551-94-0 2-(3,4-dichlorophenyl)-4-(4-fluorobenzyl)-1,2,4-thiadiazolidine-3,5-dione 
• 1055193-20-8 2-(3-chlorophenyl)-4-(4-fluorobenzyl)-1,2,4-thiadiazolidine-3,5-dione 
• 1352551-95-1 2-(3-trifluoromethylphenyl)-4-(4-fluorobenzyl)-1,2,4-thiadiazolidine-3,5-dione 
• 1352552-10-3 2-ethyl-4-(4-fluorobenzyl)-1,2,4-thiadiazolidine-3,5-dione 
• 1055193-39-9 2-n-butyl-4-(4-fluorobenzyl)-1,2,4-thiadiazolidine-3,5-dione 

Relevant academic research and scientific papers

Electron-transfer induced rearrangement of thiocyanate to isothiocyanate

Benzyl thiocyanates with an electron-withdrawing group (1a, 1b) and 9- fluorenyl thiocyanate (1e) rearrange to the corresponding isothiocyanate (2) under 9,10-diphenylanthracene (DPA) sensitization. The rearrangement would proceed via carbon-sulfur bond cleavage in an anion radical of 1 produced by photoinduced electron transfer, followed by back electron transfer to DPA·+ and recombination of the resulting radical or ion pair.

4-Dimethylaminopyridine-catalyzed synthesis of isothiocyanates from amines and carbon disulfide

Isothiocyanates were synthesized by reactions between primary amines and CS2 in the presence of 4-dimethylaminopyridine as a catalyst and tert-butyl hydroperoxide as an oxidant. Various aryl, benzyl, alkyl, and hydroxyl amines were transformed into the corresponding isothiocyanates in 41–82% yields.

Method for preparing isothiocyanate by alkali catalysis

The invention discloses a method for preparing isothiocyanate by alkali catalysis, which realizes one-step conversion from primary amine to isothiocyanate under the alkali catalysis. The method comprises the following steps: dissolving primary amine in methanol at -20 to 40 DEG C to obtain a primary amine solution, sequentially adding an alkali catalyst, carbon disulfide and an oxidant into the primary amine solution, carrying out stirring reaction, and carrying out reduced pressure distillation; finally, carrying out extraction and column chromatography purification to obtain the product; wherein the molar ratio of the primary amine to the base catalyst to the carbon disulfide to the oxidizing agent is 1: (0.05-0.2) : (2.5-10) : (1.2-4.5), the structural general formula of the primary amine is RNH2, the structural general formula of the isothiocyanate is R-N=C=S, and the R group is alkyl, aryl, benzyl or allyl. Herein, primary amine reacts with carbon disulfide under the action of analkali catalyst and an oxidizing agent to directly generate isothiocyanate, so that sulfur phosgene and excessive alkali are avoided, and the whole reaction atom economy is high, operation is simple.The method is more suitable for preparation of functional organic intermediates and active biomolecules.

Application of sulfur-containing isocyanate compounds in growth inhibition of blue-green algae

The invention relates to the application of sulfur-containing isocyanate compounds in the growth inhibition of blue-green algae. The compounds have structures as shown in a general formula I and a general formula II. In the general formula I, R1 represents a methyl group, a phenethyl group, a phenyl group, 4-methylpyridine or 3-methylpyridine. In the general formula II, M represents a carbonyl group, a methylene group and a methylene phenyl group; R3 represents hydrogen or chlorine; R4 represents oxygen, hydrogen, fluorine or chlorine; R5 represents oxygen, hydrogen, chlorine, a methyl group,fluorine, a benzene ring, bromine or a trifluoromethyl group; when R4 and R5 are oxygen, R4 and R5 are cyclized to form 1,3-dioxocyclopentene; R6 represents hydrogen, fluorine, bromine, a trifluoromethyl group, a methyl group and chlorine; and R7 represents hydrogen, a trifluoromethyl group, chlorine and bromine. The sulfur-containing isocyanate compounds with the structures as shown in the general formulas I and II provided by the invention have relatively good inhibition effect on blue-green algae, and can be used as an effective component of a blue-green algae algicide.

HETEROCYCLIC INTEGRIN AGONISTS

The present invention provides polycyclic oxothioxoimidazolidines, dioxoimidazolines, oxothioxooxazolidines, dioxooxazolidines, and related compounds, which are useful as integrin agonists. Methods for the treatment of integrin-mediated diseases such as cancer are also described.

The synthesis of sulforaphane analogues and their protection effect against cisplatin induced cytotoxicity in kidney cells

A series of sulforaphane analogues were synthesized with various amines by treatment of carbon disulfide followed by Boc2O and DMAP. These synthesized sulforaphane analogues were tested on cisplatin treated cultured LLC-PK1 kidney cell line. Among these analogues, several compounds including SF5 show a potent effect on kidney cell protection assay at the concentration of 2.5 μM. Further studies with compound SF5 revealed that the kidney cell protection effect was related by inhibiting the apoptosis pathway through JNK-p53-caspase apoptotic cascade. Compound SF5 may be considered as a promising candidate for the development of new kidney protection agent against drug induced acute kidney disease.

Enantioselective synthesis of 3,5-disubstituted thiohydantoins and hydantoins

A mild method to convert optically pure amino acid thiourea and urea derivatives to thiohydantoins and hydantoins, respectively, is described. It provides an efficient way to realize enantioselective synthesis of thiohydantoins and hydantoins with good to high isolated yields and enantiomeric purities. We found that the enantiomeric purities were highly dependent on the reaction conditions including bases, solvents, and temperature.

Synthesis and cytotoxic evaluation of quinazolin-4(3H)-one derivatives bearing thiocarbamate, thiourea or N-methyldithiocarbamate side Chains

We have previously found that the dithiocarbamate derivatives of quinazolin-4(3H)-one could act as cytotoxic agents against a panel of human tumor cell lines. To investigate the contribution of dithiocarbamate moiety to the cytotoxic activity, three series of novel quinazolin-4(3H)-one derivatives bearing thiocarbamate, thiourea or Nmethyldithiocarbamate side chains were synthesized and tested for their cytotoxic activity against human cancer cell lines A549, MCF-7, HeLa, HT29 and HCT-116 by MTT assay. The results showed that transformation of the dithiocarbamate moiety in lead compound I to thiocarbamate or thiourea led to a decrease or loss of cytotoxic activity. Some N-alkylated analogs of lead compound II preferentially inhibited the proliferation of A549 cells, although their potencies were not improved in comparison with the unalkylated counterparts. The structure-activity relationship obtained in this research will be beneficial for further synthesis and discovery of effective cytotoxic agents.

EMETINE DERIVATIVES, PRODRUGS CONTAINING SAME, AND METHODS OF TREATING CONDITIONS USING SAME

Compounds are provided herein which are emetine derivatives that can be used as prodrugs which selectively undergo activation to release emetine in specific cellular conditions. In one aspect, a blocking group is incorporated onto the emetine molecule by the derivization of the N2'-position with moieties that can be selectively removed by hydrolysis in the cancer/tumor microenvironment. Such compounds are less cytotoxic than emetine and are substantially inactive in non-cancerous cells. In one aspect, the compounds described herein can be used for the treatment of metastatic and non-metastatic cancers, including, for example, breast cancer, prostate cancer, lung cancer, and leukemia.

Structure-activity relationships (SAR) research of thiourea derivatives as dual inhibitors targeting both HIV-1 capsid and human cyclophilin A

HIV-1 capsid (CA) and human cyclophilin A (CypA) play important roles in HIV-1 assembly and disassembly processes, which are critical in HIV-1 replication. Based on the discovery of thiourea derivatives targeting both of the two proteins and indicating effective inhibitory activities in our group, we designed and synthesized a new class of thiourea derivatives. Their abilities to bind to capsid and cyclophilin A were determined by ultraviolet spectroscopic analysis, fluorescence binding affinity, and PPIase inhibition assay. Furthermore, the newly synthesized compounds were tested for their antiviral activities and cytotoxicities using CEM cells. According to the biological evaluation and subsequent molecular docking analyses, we studied the structure-activity relationships of thiourea derivatives. Three optimal compounds (K17, K24, K25) based on the achieved structure-activity relationships would be the basis for future optimization.