19241-16-8

Usage

Uses

Used in Chemical Synthesis:
2,6-DIMETHYLPHENYL ISOTHIOCYANATE is used as a key intermediate in the synthesis of various organic compounds for [application reason] enhancing the development of novel chemical entities.
Used in Analytical Chemistry:
In Analytical Chemistry, 2,6-DIMETHYLPHENYL ISOTHIOCYANATE is used as a derivatizing agent for the preparation of derivatized β-cyclodextrins, which serve as a chiral stationary phase in normal-phase liquid chromatography, allowing for the separation and analysis of enantiomers.
Used in Pharmaceutical Industry:
2,6-DIMETHYLPHENYL ISOTHIOCYANATE is used as a building block in the development of pharmaceutical compounds, such as tris(2,6-dimethylphenylimido)methylrhenium (VII) and 1-(2-isopropylphenyl)-3-(2,6-dimethylphenyl)urea, for [application reason] contributing to the advancement of drug discovery and therapeutic applications.
Used in Material Science:
In Material Science, 2,6-DIMETHYLPHENYL ISOTHIOCYANATE is used as a component in the creation of novel materials and polymers, leveraging its unique chemical properties to enhance material performance and functionality.

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

Upstream product

• 594-42-3 chlorothio-trichloro-methane 
• 87-62-7 2,6-dimethylaniline 
• 108-77-0 1,3,5-trichloro-2,4,6-triazine 
• 75-15-0 carbon disulfide 
• 2198-53-0 N-(2,6-dimethylphenyl)acetamide 
• 6160-65-2 1,1'-Thiocarbonyldiimidazole 
• 58654-90-3 2,6-dimethylphenyl dithiocarbamic acid triethylammonium 
• 103-72-0 phenyl isothiocyanate 
• 1336-21-6 ammonium hydroxide 
• 541-41-3 chloroformic acid ethyl ester 
• 7361-61-7 xylazine 
• 67-63-0 isopropyl alcohol 
• 607-92-1 2,6-dimethylformanilide 
• 787-09-7 ((2,6-dimethylphenyl)amino)phenoxymethane-1-thione 

Downstream Products

• 479373-47-2 N-(2,6-dimethylphenyl)-2-phenylhydrazine-1-carbothioamide 
• 25480-78-8 N,N′-bis(2,6-dimethylphenyl)thiourea 
• 55469-53-9 1-(2,6-dimethyl-phenyl)-3-(3-morpholin-4-yl-propyl)-thiourea 
• 58647-42-0 4-(2,6-Dimethylphenyl)-1,1-dimethyl-thiosemicarbazid 
• 24053-73-4 N¹-Methyl-N²-<2,6-dimethyl-phenyl>-N¹-benzyl-thioharnstoff 
• 63299-74-1 4-(2.6-Dimethylphenyl)-2-methylthiosemicarbazid 
• 49839-66-9 C₁₀H₁₄N₂OS 
• 63299-77-4 1.2-Dimethyl-4-(2.6-dimethylphenyl)-thiosemicarbazid 
• 63299-95-6 Aceton<4-(2.6-dimethylphenyl)-2-methylthiosemicarbazon> 
• 58647-46-4 1-(tert.-Butoxycarbonyl)-1-methyl-4-(2,6-dimethyl-phenyl)-thiosemicarbazid 
• 49839-57-8 C₁₈H₂₂N₂OS 
• 63299-81-0 2-Benzyl-4-(2,6-dimethylphenyl)-1-isopropyl-1-methyl-thiosemicarbazid 
• 63299-78-5 2-Benzyl-1,1-dimethyl-4-(2,6-dimethylphenyl)-thiosemicarbazid 
• 53300-50-8 2-(2,6-Dimethyl-phenylthiocarbamoyl)-malonic acid diethyl ester 

Relevant academic research and scientific papers

COMPOUNDS WITH COPPER- OR ZINC-ACTIVATED TOXICITY AGAINST MICROBIAL INFECTION

Heterocyclic compounds with a novel pyrazole thioamide-based NNSN structural motif, having highly effective zinc- or copper-activated toxicity against microbial infections at micromolar or nanomolar minimum inhibitory concentrations (MIC), and methods of making and using same.

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.

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.

A more sustainable isothiocyanate synthesis by amine catalyzed sulfurization of isocyanides with elemental sulfur

Isothiocyanates (ITCs) are typically prepared using amines and highly toxic reagents such as thiophosgene, its derivatives, or CS2. In this work, an investigation of a multicomponent reaction (MCR) using isocyanides, elemental sulfur and amines revealed that isocyanides can be converted to isothiocyanates using sulfur and catalytic amounts of amine bases, especially DBU (down to 2 mol%). This new catalytic reaction was optimized in terms of sustainability, especially considering benign solvents such as Cyrene or γ-butyrolactone (GBL) under moderate heating (40 °C). Purification by column chromatography was further optimized to generate less waste by maintaining high purity of the product. Thus, E-factors as low as 0.989 were achieved and the versatility of this straightforward procedure was shown by converting 20 different isocyanides under catalytic conditions, while obtaining moderate to high yields (34-95%). This journal is

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.

A novel three-component reaction between isocyanides, alcohols or thiols and elemental sulfur: A mild, catalyst-free approach towards O-thiocarbamates and dithiocarbamates

A new multicomponent reaction has been developed between isocyanides, sulfur and alcohols or thiols under mild reaction conditions to afford O-thiocarbamates and dithiocarbamates in moderate to good yields. The one-pot reaction cascade involves the formation of an isothiocyanate intermediate, thus a catalyst-free synthesis of isothiocyanates, as valuable building blocks from isocyanides and sulfur is proposed, as well. The synthetic procedure suits the demand of a modern organic chemist, as it tolerates a wide range of functional groups, it is atom economic and easily scalable.

Chemical synthesis method of 2,6-dimethylaniline thiazine

The invention discloses a chemical synthesis method of 2,6-dimethylaniline thiazine. The method comprises the following steps: dissolving dried acetyl (2,6-dimethyl) aniline into an anhydrous solution; carrying out quantitative reaction on a mixed solution and carbon disulfide under the action of metal hydride to generate isothiocyanic acid-2,6-dimethyl phenyl ester; carrying out aminolysis on theisothiocyanic acid-2,6-dimethyl phenyl ester and 3-aminopropanol to obtain 1-(2,6-dimethyl)-phenyl-3-propanolyl thiourea after drying and purifying; and catalyzing and cyclizing with concentrated hydrochloric acid to obtain a target product 2,6-dimethylaniline thiazine. The preparation method disclosed by the invention has the advantages of easily-obtained raw materials, rigorous requirements onoperating conditions, simplicity in actual production and suitability for industrial mass production.

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.

NOVEL FLAVONE BASED EGFR INHIBITORS AND PROCESS FOR PREPARATION THEREOF

The present invention discloses a novel EGFR inhibitor compound of formula (1), process for preparation thereof and methods of treating abnormal cell growth in mammals by administering the compounds of formula (1). wherein, R is selected from hydrogen, alkyl, nitro, halogens such as chlorine, bromine, fluorine and iodine; Rl= hydrogen, alkyl, alkoxy, aryl, nitro, halogens such as chlorine, bromine, fluorine and iodine, trifluoromethyl, thioalkyl, trifluromethoxy, trialkylsilyl.