1539-20-4

Usage

Uses

Used in Pharmaceutical Industry:
2,3-DIMETHYLPHENYL ISOTHIOCYANATE is used as a key intermediate in the synthesis of various pharmaceutical compounds for its ability to contribute to the development of new drugs with potential therapeutic applications.
Used in Agrochemical Industry:
In the agrochemical sector, 2,3-DIMETHYLPHENYL ISOTHIOCYANATE is utilized as a precursor in the production of agrochemicals, aiding in the creation of substances that can protect crops from pests and diseases.
Used in Chemical Research:
2,3-DIMETHYLPHENYL ISOTHIOCYANATE is employed as a reagent in chemical research for its unique properties, enabling scientists to explore new chemical reactions and syntheses.
Used in Industrial Processes:
2,3-DIMETHYLPHENYL ISOTHIOCYANATE is used in various industrial processes due to its reactivity and functional group, playing a role in the manufacturing of different types of products.
Used in Anticancer Research:
2,3-DIMETHYLPHENYL ISOTHIOCYANATE is studied for its potential as an anticancer agent, with ongoing research aimed at understanding its effects on cancer cells and its possible integration into cancer treatment strategies.

InChI:InChI=1/C9H9NS/c1-7-4-3-5-9(8(7)2)10-6-11/h3-5H,1-2H3

Upstream product

• 463-71-8 thiophosgene 
• 5417-45-8 2,3-dimethylaniline hydrochloride 
• 87-59-2 2,3-Dimethylaniline 
• 75-15-0 carbon disulfide 
• 88101-26-2 N,N'-bis-(2,3-dimethyl-phenyl)-thiourea 
• 108-24-7 acetic anhydride 
• 108654-37-1 ammonium 2,3-dimethylphenyl dithiocarbamate 

Downstream Products

• 110030-34-7 aziridine-1-carbothioic acid-(2,3-dimethyl-anilide) 
• 94772-11-9 (2,3-dimethyl-phenyl)-thiocarbamic acid O-ethyl ester 
• 108774-55-6 hydrazine-N,N'-bis-carbothioic acid anilide-(2,3-dimethyl-anilide) 
• 38103-22-9 1-{[(E)-4-Chloro-2-methyl-phenylimino]-methyl}-3-(2,3-dimethyl-phenyl)-1-methyl-thiourea 
• 139004-27-6 4,4'-Di(2,3-dimethylphenyl)bis-malonylthiosemicarbazide 
• 74180-77-1 thioguanine 
• 168144-56-7 C₂₀H₂₅N₅OS₂ 
• 139004-40-3 3,3'-Bis(4-(2,3-dimethylphenyl)-5-mercapto-1,2,4-triazol) 
• 139004-33-4 2,2'-Bis(5-(2,3-dimethylphenylamino)-1,3,4-thiadiazol) 
• 139004-43-6 Bis(4-(2,3-dimethylphenyl)-5-mercapto-1,2,4-triazol-3-yl)methane 
• 139004-36-7 Bis(5-(2,3-dimethylphenylamino)-1,3,4-thiadiazol-2-yl)methane 
• 36314-60-0 (4,5-dihydro-thiazol-2-yl)-(2,3-dimethyl-phenyl)-amine 
• 891089-69-3 N-(2,3-dimethylphenyl)-2-(2-methylbenzoyl)hydrazinecarbothioamide 
• 519043-39-1 N-(2,3-dimethylphenyl)-2-(benzoyl)hydrazinecarbothioamide 

Relevant academic research and scientific papers

A catalyst-free method for the synthesis of 1,4,2-dithiazoles from isothiocyanates and hydroxylamine triflic acid salts

A catalyst-free method for the preparation of 1,4,2-dithiazoles is developed by reactions of isothiocyanates with hydroxylamine triflic acid salts. This reaction achieves C-S, C-N, and S-N bond formation, and a range of products are obtained in moderate to good yields. The obvious feature is using shelf-stable hydroxylamine triflic acid salts as a N source to synthesize heterocycles under mild conditions.

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.

Facile and versatile synthesis of alkyl and aryl isothiocyanates by using triphosgene and cosolvent

A mild and efficient method for the conversion of alkyl and aryl amines to isothiocyanates via dithiocarbamates has been developed using (CH 3)2CO-CS2 as co-solvent and triphosgene as dehydrosulfurization reagent. High yields, mild reaction conditions and excellent functional group compatibility make it become a versatile synthetic method for the preparation of isothiocyanates compared with reported methods. [Supplementary materials are available for this article. Go to the publisher's online edition of Synthetic Communications for the following free supplemental resource(s): Full experimental and spectral details.]

Synthesis, acetylcholinesterase and alkaline phosphatase inhibition of some new 1,2,4-triazole and 1,3,4-thiadiazole derivatives

A new series of 4,5-disubstituted-2,4-dihydro-3H-1,2,4-triazole-3-thiones (6as) and 2,5-disubstituted-1,3,4-thiadiazoles (7ah) was synthesized by intramolecular dehydrocyclization of various 1,4-disubstituted thiosemicarbazide derivatives (5as) by refluxing in 4N aqueous sodium hydroxide and by overnight stirring with polyphosphoric acid, respectively. The structures of these compounds were characterized by IR, 1H and 13C NMR, elemental analysis and mass spectroscopic studies. All the synthesized compounds were screened for their acetylcholinesterase and alkaline phosphatase inhibition studies. Most of the tested compounds showed promising activities, amongst them (6k) and (6q) showed excellent acetylcholinesterase inhibitory activity with IC50 0.2410.012 and 0.2600.013M, respectively, as compared with those of standard drug whereas the compound (6p), with IC50 0.0440.001M, was found to be the most potent inhibitor of alkaline phosphatase.

Diversity-orientated synthesis of 3,5-bis(arylamino)pyrazoles

The synthesis of differentially-substituted 3,5-bis(arylamino)pyrazoles has not yet been documented. During our investigation, we managed to develop a novel, entirely combinatorial synthesis of 3,5-bis(arylamino)pyrazoles relying on a simple one-pot two-step operation.

Synthesis, antioxidant activities and urease inhibition of some new 1,2,4-triazole and 1,3,4-thiadiazole derivatives

New series of 4,5-disubstituted-2,4-dihydro-3H-1,2,4-triazole-3-thiones (8a-j) and 2,5-disubstituted-1,3,4-thiadiazoles (9a-h) were synthesized by dehydrative cyclization of hydrazinecarbothioamide derivatives (7a-k) by refluxing in 4 N aqueous sodium hydroxide and by overnight stirring with polyphosphoric acid, respectively. The structures of the newly synthesized compounds were characterized by IR, 1H NMR, 13C NMR, elemental analysis and mass spectroscopic studies and the synthesized compounds were screened for their antioxidant and urease inhibition activities. N-(2,4-Dimethylphenyl)-5-(4-nitrophenyl)-1,3,4-thiadiazol-2-amine (9h) showed excellent antioxidant activity more than the standard drug whereas 4-(2,4-dimethylphenyl)-5-(3-nitrophenyl)-2,4-dihydro-3H-1,2,4-triazole-3-thione (8d) and 4-(2,3-dimethylphenyl)-5-phenyl-2,4-dihydro-3H-1,2,4-triazole-3-thione (8e) exhibited potent urease inhibitory activities.

Thiazolidinone CFTR inhibitors with improved water solubility identified by structure-activity analysis

The thiazolidinone 3-[(3-trifluoromethyl)phenyl]-5-[(4-carboxyphenyl)methylene]-2-thioxo-4-thiazolidinone (CFTRinh-172) inhibits cystic fibrosis transmembrane conductance regulator (CFTR) chloride channel conductance with submicromolar affinity and blocks cholera toxin-induced intestinal fluid secretion. Fifty-eight CFTRinh-172 analogs were synthesized to identify CFTR inhibitors with improved water solubility, exploring modifications in its two phenyl rings, thiazolidinone core, and core-phenyl connectors. Greatest CFTR inhibition potency was found for 3-CF3 and polar group-substituted-phenyl rings, and a thiazolidinone core. Two compounds with ～1 μM CFTR inhibition potency and solubility >180 μM (>10-fold more than CFTRinh-172) were identified: Tetrazolo-172, containing 4-tetrazolophenyl in place of 4-carboxyphenyl, and Oxo-172, containing thiazolidinedione in place of the thiazolidinone core. These water soluble thiazolidinone analogs had low cellular toxicity. The improved water solubility of Tetrazolo- and Oxo-172 make them potential lead candidates for therapy of secretory diarrheas and polycystic kidney disease.

2-Arylimino-5,6-dihydro-4H-1,3-thiazines as a new class of cannabinoid receptor agonists. Part 2: Orally bioavailable compounds

Structure-activity relationships and efforts to optimize the pharmacokinetic profile of a class of 2-arylimino-5,6-dihydro-4H-1,3-thiazines as cannabinoid receptor agonists are described. Among the compounds examined, compound 14 showed potent affinity and high selectivity for CB2, and compound 23 showed potent affinities against CB1 and CB2. These compounds displayed oral bioavailability.

Synthesis of thiophene-2-carboxamidines containing 2-aminothiazoles and their biological evaluation as urokinase inhibitors

The serine protease urokinase (uPa) has been implicated in the progression of both breast and prostate cancer. Utilizing structure based design, the synthesis of a series of substituted 4-[2-amino-1,3-thiazolyl]-thiophene-2-carboxamidines is described. Further optimization of this series by substitution of the terminal amine yielded urokinase inhibitors with excellent activities.