24277-44-9

Usage

Chemical Properties

Clear yellow liquid

InChI:InChI=1/C9H9NS/c1-8(10-7-11)9-5-3-2-4-6-9/h2-6,8H,1H3/t8-/m1/s1

Upstream product

• 100-42-5 styrene 
• 540-72-7 sodium thiocyanide 
• 60211-92-9 (2-iodo-1-isothiocyanato-ethyl)-benzene 
• 124908-16-3 1-phenylethyl thiocyanate 
• 592-85-8 mercury(II) thiocyanate 
• 585-71-7 (1-bromoethyl)benzne 
• 98-85-1 1-Phenylethanol 
• 17356-08-0 thiourea 
• 202061-61-8 2-phenylpropanohydroximoyl chloride 
• 463-71-8 thiophosgene 
• 7664-93-9 sulfuric acid 
• 618-36-0 rac-methylbenzylamine 
• 59647-78-8 2-phenylpropanal oxime 
• 76926-65-3 C₁₁H₁₅NS₂ 

Downstream Products

• 67398-34-9 N-(α-methylbenzyl)thiourea 
• 29876-59-3 racem.-N,N'-bis-(1-phenyl-ethyl)-thiourea 
• 76176-60-8 N,N-dimethyl-N'-(1-phenyl-ethyl)-thiourea 
• 21076-44-8 4-(α-Methyl-benzyl)-2-isopropyl-thiosemicarbazid 
• 1536-14-7 Thio-bis- 
• 4312-19-0 4-(1-phenyl-ethyl)-thiosemicarbazide 
• 61079-02-5 4r-methyl-4,5c-diphenyl-oxazolidine-2-thione 
• 61079-02-5 4r-methyl-4,5t-diphenyl-oxazolidine-2-thione 
• 74548-48-4 1,1-Bis-(2-hydroxy-ethyl)-3-(1-phenyl-ethyl)-thiourea 
• 4312-18-9 4-(α-Methyl-benzyl)-2-methyl-thiosemicarbazid 
• 13120-06-4 N-methyl-N'-((+/-)-α-methylbenzyl)thiourea 
• 74548-49-5 1-(3-Hydroxy-propyl)-3-(1-phenyl-ethyl)-thiourea 
• 131156-76-8 4-Methyl-4-phenylthiazolidine-2,5-dithione 
• 116986-60-8 5-Amino-3-morpholin-4-yl-[1,2,4]triazole-1-carbothioic acid (1-phenyl-ethyl)-amide 

Relevant academic research and scientific papers

Synthesis of isothiocyanates using DMT/NMM/TsO? as a new desulfurization reagent

Thirty-three alkyl and aryl isothiocyanates, as well as isothiocyanate derivatives from esters of coded amino acids and from esters of unnatural amino acids (6-aminocaproic, 4-(aminomethyl)benzoic, and tranexamic acids), were synthesized with satisfactory or very good yields (25–97%). Synthesis was performed in a “one-pot”, two-step procedure, in the presence of organic base (Et3 N, DBU or NMM), and carbon disulfide via dithiocarbamates, with 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium toluene-4-sulfonate (DMT/NMM/TsO? ) as a desulfurization reagent. For the synthesis of aliphatic and aromatic isothiocyanates, reactions were carried out in a microwave reactor, and selected alkyl isothiocyanates were also synthesized in aqueous medium with high yields (72–96%). Isothiocyanate derivatives of L-and D-amino acid methyl esters were synthesized, under conditions without microwave radiation assistance, with low racemization (er 99 > 1), and their absolute configuration was confirmed by circular dichroism. Isothiocyanate derivatives of natural and unnatural amino acids were evaluated for antibacterial activity on E. coli and S. aureus bacterial strains, where the most active was ITC 9e.

Synthesis and antitumor activity of novel pyridazinone derivatives containing 1,3,4-thiadiazole moiety

A series of novel pyridazinone derivatives containing the 1,3,4-thiadiazole moiety were synthesized and characterized by 1H NMR, 13C NMR, spectroscopies HRMS and IR. Among them, the structure of compound 5c (2-(Tert-butyl)?4-chloro-5-((5-((2-ethylphenyl)amino)?1,3,4-thiadiazol-2-yl)thio)pyridazin-3(2H)-One) was unambiguously confirmed via single crystal X-ray diffraction analysis. The inhibitory activity of all the target compounds against MGC-803 and Bcap-37 was determined by MTT assay, with doxorubicin (the inhibition rates were 95.5 ± 0.4% and 95.7 ± 1.0% respectively) as a control. The preliminary results showed that the inhibitory activity of compound 5n (2-(Tert-butyl)?4-chloro-5-((5-((3-fluorophenyl)amino)?1,3,4-thiadiazol-2-yl)thio)pyridazin-3(2H)-One) was superior to the others. The inhibition rates of MGC-803 and Bcap-37 cells were 86.3 ± 2.2% and 92.3 ± 0.6% at a concentration of 10 μmol/L, respectively. The preliminary structure-activity relationship showed that when the 2-position of the benzene ring was substituted by a methyl group, such as compound 5j (2-(Tert-butyl)?4-chloro-5-((5-((2,3-dimethylphenyl)amino)?1,3,4-thiadiazol-2-yl)thio)pyridazin-3(2H)-One), it exhibited good anticancer activity on MGC-803 cells. Besides, introducing fluorine, chlorine, or trifluoromethyl group onto the benzene ring, such as compound 5 m (2-(Tert-butyl)?4-chloro-5-((5-((4-(trifluoromethoxy)phenyl)amino)?1,3,4-thiadiazol-2-yl)thio)pyridazin-3(2H)-One), displayed good anticancer activity on MGC-803 and Bcap-37 cells.

Direct, Microwave-Assisted Synthesis of Isothiocyanates

A microwave-assisted desulfuration of readily available dithiocarbamates, formed in situ from primary amines, leading to target isothiocyanates has been developed. This efficient protocol provides a rapid, environmentally benign route to aliphatic and aromatic isothiocyanates.

Na2S2O8-mediated efficient synthesis of isothiocyanates from primary amines in water

We have developed two green, practical, and efficient procedures, including a one-pot one, to synthesize isothiocyanates from amines and carbon disulfide via desulfurization with sodium persulfate. Water is used as the solvent. Basic conditions are necessary for good chemoselectivity for isothiocyanates. Structurally diverse linear and branched alkyl amines and aryl amines are readily converted to isothiocyanates by the two procedures in satisfactory yields. Halogens, benzylic C-H bonds, methylthio, nitro, ester, alkenyl, electron-rich or -deficient (hetero)aryls, acetylenyl, and even phenolic and alcoholic hydroxyls are well tolerated. The one-pot procedure in water can also be used to realize the preparation of chiral isothiocyanates from chiral amines, and the modification of bioactive structures with free amino groups. In large-scale preparation, simple and practical purification procedures independent of column chromatography are developed.

T3P - A Benign Desulfurating Reagent in the Synthesis of Isothiocyanates

A number of alkyl, aryl and bifunctional isothiocyanates are obtained in moderate to high yields (41-94%) in a two-step, one-pot reaction of the parent primary amines or their salts with carbon disulfide, followed by reaction of the thus formed dithiocarbamates with T3P (propane phosphonic acid anhydride) as a new and efficient desulfurating agent.

Reaction of Thiocarbonyl Fluoride Generated from Difluorocarbene with Amines

The reaction of thiocarbonyl fluoride, generated from difluorocarbene, with various amines under mild conditions is described. Secondary amines, primary amines, and o-phenylenediamines are converted to thiocarbamoyl fluorides, isothiocyanates, and difluoromethylthiolated heterocycles, respectively. Thiocarbamoyl fluorides were further transformed into trifluoromethylated amines by using a one-pot process. Thiocarbonyl fluoride is generated in situ and is rapidly fully converted in one pot under mild conditions; therefore, no special safety precautions are needed.

Synthesis, molecular modeling, and biological evaluation of novel chiral thiosemicarbazone derivatives as potent anticancer agents

A series of new chiral thiosemicarbazones derived from homochiral amines in both enantiomeric forms were synthesized and evaluated for their in vitro antiproliferative activity against A549 (human alveolar adenocarcinoma), MCF-7 (human breast adenocarcinoma), HeLa (human cervical adenocarcinoma), and HGC-27 (human stomach carcinoma) cell lines. Some of compounds showed inhibitory activities on the growth of cancer cell lines. Especially, compound 17b exhibited the most potent activity (IC50 4.6 μM) against HGC-27 as compared with the reference compound, sindaxel (IC50 10.3 μM), and could be used as a lead compound to search new chiral thiosemicarbazone derivatives as antiproliferative agents.

Optically active helical polymers with pendent thiourea groups: Chiral organocatalyst for asymmetric michael addition reaction

This article reports a novel category of helical substituted polyacetylenes bearing pendant thiourea groups and showing remarkable asymmetric catalysis ability. Thiourea-based monomer and another chiral monomer underwent copolymerization, affording copoly

Contrasting Reactivity of CS2 with Cyclic vs. Acyclic Amidines

The interaction between carbon dioxide (CO2) and amidines such as 1,8-diazabicyclo[5.4.0]undecane (DBU) has been extensively studied, but the reaction of isovalent CS2 with such bases has been largely ignored, apart from a single crystallography report. Acyclic acetamidines are cleaved by CS2 at room temperature to give an isothiocyanate and a thioacetamide. Because the pathway to that cleavage involves a rotation that is difficult for cyclic amidines, the reaction of CS2 with cyclic amidines produces an entirely different product: a cyclic carbamic carboxylic trithioanhydride structure. The path to that product involves sp3 C-H activation leading to the formation of a new C-C bond at a carbon α to the central carbon of the amidine group. Alkylation and ring-opening of the cyclic carbamic carboxylic trithioanhydride has also been demonstrated under ambient conditions.