2131-64-8

Usage

Uses

Used in Organic Synthesis:
4-(DIMETHYLAMINO)PHENYL ISOTHIOCYANATE is used as a reagent for introducing isothiocyanate functional groups into various molecules, which is crucial in the synthesis of a wide range of organic compounds.
Used in Medicinal Chemistry and Drug Development:
4-(DIMETHYLAMINO)PHENYL ISOTHIOCYANATE is used as a modifier in the development of new drugs, where its ability to alter the properties of organic compounds can lead to the creation of more effective pharmaceuticals.
Used in Biochemical and Immunological Assays:
4-(DIMETHYLAMINO)PHENYL ISOTHIOCYANATE is used as a fluorescent label in biochemical and immunological assays, taking advantage of its fluorescence properties to aid in the detection and analysis of biological molecules.

InChI:InChI=1/C9H10N2S/c1-11(2)9-5-3-8(4-6-9)10-7-12/h3-6H,1-2H3

Upstream product

• 13991-81-6 N,N'-bis-(4-dimethylamino-phenyl)-thiourea 
• 103-72-0 phenyl isothiocyanate 
• 99-98-9 4-amino-N,N-dimethylaniline 
• 57-06-7 N-allyl isothiocyanate 
• 200337-28-6 N,N-Dimethyl-N'-[1,3]thiazepan-(2Z)-ylidene-benzene-1,4-diamine 
• 75-44-5 phosgene 
• 463-71-8 thiophosgene 
• 2052-46-2 N,N-dimethyl-p-phenylenediamine hydrochloride 
• 96989-50-3 di-2-pyridyl thionocarbonate 
• 75-15-0 carbon disulfide 
• 16420-13-6 N,N-Dimethylthiocarbamoyl chloride 
• 81290-20-2 (trifluoromethyl)trimethylsilane 
• 29647-71-0 o-phenyl [4-(dimethylamino)phenyl]carbamothioate 
• 1005-56-7 phenylcarbonochloridothioate 

Downstream Products

• 109437-39-0 piperidine-1-carbothioic acid-(4-dimethylamino-anilide) 
• 15863-28-2 N-cyclohexyl-N'-p-dimethylaminophenyl-thiourea 
• 31979-44-9 N-(4-ethoxy-phenyl)-N'-(4-dimethylamino-phenyl)-thiourea 
• 56610-80-1 1-(4-dimethylamino-phenyl)-1,4-dihydro-tetrazole-5-thione 
• 76609-49-9 4-(4'-(dimethylamino)phenyl)-3-thiosemicarbazide 
• 22283-43-8 1-(4-Dimethylaminophenyl)-thioharnstoff 
• 59995-04-9 N,N-dimethyl-N'-[1,2,3]thiadiazol-5-yl-benzene-1,4-diamine 
• 135242-87-4 N,N-dimethyl-N'-thiazolo[5,4-b]pyridin-2-yl-benzene-1,4-diamine 
• 64892-77-9 N,N-dimethyl-N'-(3-methyl-5-methylene-thiazolidin-2-ylidene)-benzene-1,4-diamine 
• 64892-79-1 N'-(3,5-dimethyl-3H-thiazol-2-ylidene)-N,N-dimethyl-benzene-1,4-diamine 
• 51027-69-1 4-(dimethylamino)aniline 
• 4953-65-5 N-(4-dimethylaminophenyl)cyanothioformanilide 
• 64892-92-8 N'-(3-cyclopentyl-5-methylene-thiazolidin-2-ylidene)-N,N-dimethyl-benzene-1,4-diamine 
• 64892-98-4 N,N-dimethyl-N'-(4-methylene-3-thia-1-aza-spiro[4.5]dec-1-en-2-yl)-benzene-1,4-diamine 

Relevant academic research and scientific papers

Fluorescence detection of iodide anion using a donor-acceptor (D-A) thiourea derivative

1-(4-acetyl-phenyl)-3-(4-N,N-dimethylaminophenyl)-thiourea is synthesized and characterized by NMR, IR, MS and elemental analysis. The probe exhibits the "turn-off" fluorescence response to iodide anion in THF/H2O (v/v = 9/1) pH = 7.4 Tris-HCl buffer solution, which is attributed to the intramolecular charge transfer (ICT). It is found that the probe has a detection limit of 0.336 μM. Such interesting results could be further supported by quantum chemical calculation, UV and 1H NMR titration. Moreover, the probe is applied to determine iodide in powdered milk and urine samples. This experiment shows a good agreement between added and detected concentration of the iodide in real samples.

1,3-Thiazepines. 2. Reaction of 2-iminohexahydrothiazepines with phenylisocyanate and isothiocyanates

We have shown that as a result of reaction of phenylisocyanate with 2-benzyl- and 2-aryliminohexahydrothiazepines, the corresponding N-substituted N-tetrahydroazepinyl-N′-phenylureas are formed. In the case of isothiocyanates, on boiling in different solvents we obtained the products of the exchange reaction; and at room temperature, we also obtained substituted thioureas. We suggest a probable scheme for the process. 1997 Plenum Publishing Corporation.

Synthesis methods for isothiocyanate derivative

The invention discloses synthesis methods for an isothiocyanate derivative. The first synthesis method includes reacting raw materials, including primary amine, trifluoromethyltrimethylsilane, potassium fluoride and sulfur, with an organic solvent at the room temperature to obtain the isothiocyanate derivative. The synthetic isothiocyanate derivative has the advantages of simple operation, safety,high efficiency, non-toxicity, low raw material price, mild condition, high yield, wide application range of substrates, high compatibility of functional groups and the like. The second synthesis method includes reacting raw materials, including the primary amine, silver trifluoromethane and potassium bromide, with the organic solvent at the room temperature to obtain the isothiocyanate derivative. The isothiocyanate derivative has the advantages of simple operation, safety, high efficiency, easy availability of the raw materials, nearly quantitative yield, wide application range of the substrates, applicability to selective post-modification of drugs or complex compounds, and the like.

Synthesis of thiocarbamoyl fluorides and isothiocyanates using CF3SiMe3 and elemental sulfur or AgSCF3 and KBr with amines

Reactions of thiocarbonyl fluoride derived from cheap, readily available, and widely used CF3SiMe3, elemental sulfur, and KF with secondary amines and primary amines at room temperature in THF provided a wide variety of thiocarbamoyl fluorides and isothiocyanates in moderate to excellent yields, respectively. The two reactions show broad substrate scope and good functional group tolerance. Moreover, AgSCF3 reacts with secondary/primary amines under KBr at room temperature, affording quantitative thiocarbamoyl fluorides/isothiocyanates, which feature late-stage application.

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.

Alkali-free green synthetic isothiocyanate method

The invention discloses an alkali-free green synthetic method for isothiocyanate, and relates to the field of organic chemical industry. The method includes the steps: (1) adding solvents into carbon sulfide reagents and primary amine serving as raw materials, performing organic reaction at the temperature of 100-150 DEG C for 10-30 hours; (2) cooling and spin-drying the raw materials after reaction, adding dichloromethane, extracting and separating organic phases by 10% of dilute hydrochloride acid, washing the organic phases, combining the organic phases into an organic layer, washing the organic layer with saturated salt water, drying the organic layer by anhydrous Na2SO4, and performing column chromatographic separation to obtain the isothiocyanate. The molar ratio of the carbon sulfide reagents to the primary amine is 1:1.2-3. Compared with a preparation method in the prior art, the method has the advantages that only heating reaction needs to be performed in the solvents, additional alkali is omitted, and the method is greener and more environmentally friendly and has better application values.

Aminothiazole compound, and preparation method and application thereof

The invention discloses an aminothiazole compound, and a preparation method and an application thereof. The compound has a following structural formula. In the formula, n, m, x are all 0 or 1, and only one of the three is 1 or the three are 0 at a same time; R1 is hydrogen, 2-pyridyl, 3-pyridyl, 4-pyridyl, phenyl, 2-pyrazinyl, 2-furyl, 2-thienyl, 2-pyrrolyl, 2-quinolyl, or 2-methylenepyridine; R2 is hydrogen or alkane with 1-10 aliphatic carbon chains; R3 or R4 is hydrogen or as the picture; R5 is hydrogen, a structure as the picture, N,N-diethyl, N,N-dipropyl, methyl, ethyl, propyl, butyl, trifluoromethyl, methoxy or cyano; among R3, R4 and R5, two are hydrogen at a same time; R6 and R7 can be same or different, and can be H, alkane with 1-10 aliphatic carbon chains, olefin or alkyne. In animal bodies, the compounds can inhibit the proliferation and growth of KRAS high mutant tumors such as pancreatic cancer and colon cancer.

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.

Synthesis of isothiocyanates by reaction of amines with phenyl chlorothionoformate via one-pot or two-step process

A facile and efficient synthesis of isothiocyanates from amines is described. This method involves the reaction of amines with phenyl chlorothionoformate in the presence of solid sodium hydroxide by either a one-pot process or a two-step approach. The one-pot process is useful for preparing alkyl and electron-rich aryl isothiocyanates, whereas the two-step approach is more versatile, working very well not only for alkyl and electron-rich aryl isothiocyanates, but also for highly electron-deficient aryl and heterocyclic isothiocyanates. Georg Thieme Verlag Stuttgart, New York.

Synthesis and SAR of selective small molecule neuropeptide y Y2 receptor antagonists

Highly potent and selective small molecule neuropeptide Y Y2 receptor antagonists are reported. The systematic SAR exploration of a hit molecule N-(4-ethoxyphenyl)-4-[hydroxy(diphenyl)methyl]piperidine-1-carbothioamide, identified from HTS, led to the discovery of highly potent NPY Y2 antagonists 16 (CYM 9484) and 54 (CYM 9552) with IC50 values of 19 nM and 12 nM respectively.