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3,4-DIMETHOXYPHENYL ISOTHIOCYANATE is a chemical compound with the molecular formula C10H9NO2S. It is an isothiocyanate derivative known for its strong odor and pale yellow color. 3,4-DIMETHOXYPHENYL ISOTHIOCYANATE is characterized by its reactivity in chemical reactions, particularly with nucleophiles, and is commonly used as a building block in organic chemistry for the synthesis of various pharmaceuticals, agrochemicals, and other fine chemicals. Its ability to react with biomolecules and form covalent bonds also makes it a promising candidate for biological research and drug discovery.

33904-04-0

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33904-04-0 Usage

Uses

Used in Organic Synthesis:
3,4-DIMETHOXYPHENYL ISOTHIOCYANATE is used as a building block in organic synthesis for the creation of various pharmaceuticals, agrochemicals, and other fine chemicals. Its reactivity with nucleophiles makes it a valuable component in the development of new compounds with potential applications in various industries.
Used in Biological Research:
3,4-DIMETHOXYPHENYL ISOTHIOCYANATE is used as a research tool in biological studies due to its ability to react with biomolecules and form covalent bonds. This property allows scientists to develop new tools for studying cellular processes and drug discovery, potentially leading to the creation of novel therapeutic agents and diagnostic methods.
Used in Drug Discovery:
3,4-DIMETHOXYPHENYL ISOTHIOCYANATE is employed in drug discovery as a starting material for the synthesis of new pharmaceutical compounds. Its reactivity and versatility in chemical reactions enable the development of innovative drugs with potential therapeutic benefits in various medical fields.
Used in Agrochemicals:
In the agrochemical industry, 3,4-DIMETHOXYPHENYL ISOTHIOCYANATE is used as a key intermediate in the synthesis of various agrochemicals, such as pesticides and herbicides. Its reactivity and ability to form stable covalent bonds contribute to the development of effective and environmentally friendly agricultural products.

Check Digit Verification of cas no

The CAS Registry Mumber 33904-04-0 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 3,3,9,0 and 4 respectively; the second part has 2 digits, 0 and 4 respectively.
Calculate Digit Verification of CAS Registry Number 33904-04:
(7*3)+(6*3)+(5*9)+(4*0)+(3*4)+(2*0)+(1*4)=100
100 % 10 = 0
So 33904-04-0 is a valid CAS Registry Number.
InChI:InChI=1/C9H9NO2S/c1-11-8-4-3-7(10-6-13)5-9(8)12-2/h3-5H,1-2H3

33904-04-0 Well-known Company Product Price

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  • Alfa Aesar

  • (B21415)  3,4-Dimethoxyphenyl isothiocyanate, 99%   

  • 33904-04-0

  • 1g

  • 338.0CNY

  • Detail
  • Alfa Aesar

  • (B21415)  3,4-Dimethoxyphenyl isothiocyanate, 99%   

  • 33904-04-0

  • 5g

  • 1283.0CNY

  • Detail
  • Alfa Aesar

  • (B21415)  3,4-Dimethoxyphenyl isothiocyanate, 99%   

  • 33904-04-0

  • 25g

  • 2818.0CNY

  • Detail

33904-04-0SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 11, 2017

Revision Date: Aug 11, 2017

1.Identification

1.1 GHS Product identifier

Product name 4-isothiocyanato-1,2-dimethoxybenzene

1.2 Other means of identification

Product number -
Other names 3,4-dimethoxybenzenisothiocyanate

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:33904-04-0 SDS

33904-04-0Relevant articles and documents

Discovery of boronic acid-based potent activators of tumor pyruvate kinase M2 and development of gastroretentive nanoformulation for oral dosing

Patle, Rajkumar,Shinde, Shital,Patel, Sagarkumar,Maheshwari, Rahul,Jariyal, Heena,Srivastava, Akshay,Chauhan, Neelam,Globisch, Christoph,Jain, Alok,Tekade, Rakesh K.,Shard, Amit

supporting information, (2021/05/19)

Several studies have established that cancer cells explicitly over-express the less active isoform of pyruvate kinase M2 (PKM2) is critical for tumorigenesis. The activation of PKM2 towards tetramer formation may increase affinity towards phosphoenolpyruvate (PEP) and avoidance of the Warburg effect. Herein, we describe the design, synthesis, and development of boronic acid-based molecules as activators of PKM2. The designed molecules were inspired by existing anticancer scaffolds and several fragments were assembled in the derivatives. 6a-6d were synthesized using a multi-step synthetic strategy in 55–70% yields, starting from cheap and readily available materials. The compounds were selectively cytotoxic to kill the cancerous cells at 80 nM, while they were non-toxic to the normal cells. The kinetic studies established the compounds as novel activators of PKM2 and (E/Z)-(4-(3-(2-((4-chlorophenyl)amino)-4-(dimethylamino)thiazol-5-yl)-2-(ethoxycarbonyl)-3-oxoprop-1-en-1-yl) phenyl)boronic acid (6c) emerged as the most potent derivative. 6c was further evaluated using various in silico tools to understand the molecular mechanism of tetramer formation. Docking studies revealed that 6c binds to the PKM2 dimer at the dimeric interface. Further to ascertain the binding site and mechanism of action, rigorous MD (molecular dynamics) simulations were undertaken, which led to the conclusion that 6c stabilizes the center of the dimeric interface that possibly promotes tetramer formation. We further planned to make a tablet of the developed molecule for oral delivery, but it was seriously impeded owing to poor aqueous solubility of 6c. To improve aqueous solubility and retain 6c at the lower gastrointestinal tract, thiolated chitosan-based nanoparticles (TCNPs) were prepared and further developed as tablet dosage form to retain anticancer potency in the excised goat colon. Our findings may provide a valuable pharmacological mechanism for understanding metabolic underpinnings that may aid in the clinical development of new anticancer agents targeting PKM2.

Synthesis, in-vitro antiprotozoal activity and molecular docking study of isothiocyanate derivatives

Al-Harrasi, Ahmed,Babanezhad Harikandei, Kosar,Bararjanian, Morteza,Ebrahimi, Samad Nejad,Kaiser, Marcel,Salehi, Peyman

, (2019/12/09)

Novel isothiocyanate derivatives were synthesized starting from noscapine, bile acids, amino acids, and some aromatic compounds. Antiparasitic activities of the synthesized derivatives were tested against four unicellular protozoa, i.e., Trypanosoma brucei rhodesiense, T. cruzi, Leishmania donovani, and Plasmodium falciparum. Interestingly, seven isothiocyanate analogues displayed promising antiparasitic activity against Leishmania donovani with IC50 values between 0.4 and 1.0 μM and selectivity index (SI) ranged from 7.8 to 18.4, comparable to the standard drug miltefosine (IC50 = 0.7 μM). Compound 7h demonstrated the best antileishmanial activity with an IC50 value of 0.4 μM. Seven products exhibited inhibition activity against T. brucei rhodesiense with IC50s below 2.0 μM and SI between 2.7 and 29.3. Four primary amine derivatives of noscapine and five isothiocyanate derivatives exhibited antiplasmodial activity with IC50s in the range of 1.1–2.7 μM and SI values between 1.1 and 14.5. The isothiocyanate derivative 7c showed against T. cruzi with an IC50 value of 1.9 μM and SI 4. Molecular docking and ADMET studies were performed to investigate the interaction between active ligands and T. brucei trypanothione reductase active site. The docking studies showed significant binding affinity of noscapine derivatives to enzyme active site and good compatibility with experimental data.

Synthesis and evaluation of frentizole-based indolyl thiourea analogues as MAO/ABAD inhibitors for Alzheimer's disease treatment

Hroch, Lukas,Guest, Patrick,Benek, Ondrej,Soukup, Ondrej,Janockova, Jana,Dolezal, Rafael,Kuca, Kamil,Aitken, Laura,Smith, Terry K.,Gunn-Moore, Frank,Zala, Dominykas,Ramsay, Rona R.,Musilek, Kamil

, p. 1143 - 1152 (2017/02/05)

Alzheimer's disease (AD) is a neurodegenerative disorder associated with an excessive accumulation of amyloid-beta peptide (Aβ). Based on the multifactorial nature of AD, preparation of multi-target-directed ligands presents a viable option to address more pathological events at one time. A novel class of asymmetrical disubstituted indolyl thioureas have been designed and synthesized to interact with monoamine oxidase (MAO) and/or amyloid-binding alcohol dehydrogenase (ABAD). The design combines the features of known MAO inhibitors scaffolds (e.g. rasagiline or ladostigil) and a frentizole moiety with potential to interact with ABAD. Evaluation against MAO identified several compounds that inhibited in the low to moderate micromolar range. The most promising compound (19) inhibited human MAO-A and MAO-B with IC50values of 6.34 μM and 0.30 μM, respectively. ABAD activity evaluation did not show any highly potent compound, but the compound series allowed identification of structural features to assist the future development of ABAD inhibitors. Finally, several of the compounds were found to be potent inhibitors of horseradish peroxidase (HRP), preventing the use of the Amplex Red assay to detect hydrogen peroxide produced by MAO, highlighting the need for serious precautions when using an enzyme-coupled assay.

Pyrazolopyrimidines: Potent Inhibitors Targeting the Capsid of Rhino- and Enteroviruses

Makarov, Vadim A.,Braun, Heike,Richter, Martina,Riabova, Olga B.,Kirchmair, Johannes,Kazakova, Elena S.,Seidel, Nora,Wutzler, Peter,Schmidtke, Michaela

supporting information, p. 1629 - 1634 (2015/10/06)

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.

A highly efficient methodology for 5-methyl-3-aryl-2-thiooxazolidin-4-ones using lithium perchlorate in DIPEA mediated synthesis

Khatik, Gopal L.,Pal, Anang,Apsunde, Tushar D.,Nair, Vipin A.

experimental part, p. 734 - 739 (2010/08/22)

(Chemical Equation Presented) An efficient methodology for the synthesis of 5-methyl-3-aryl-2-thiooxazolidin-4-ones from aryl isothiocyanates has been developed. Aryl isothiocyanates, synthesized from various anilines, were converted to the desired compounds by treating with ethyl lactate in presence of DIPEA and catalytic amount of lithium perchlorate. This method provides a convenient and cost-effective strategy, with no specific purification protocol.

Synthesis of APTRA derivatives as building blocks for low-affinity fluorescent Ca2+ indicators

Metten, Bert,Smet, Mario,Boens, Noel,Dehaen, Wim

, p. 1838 - 1844 (2007/10/03)

A new method for the synthesis of trialkyl aminophenoltriacetates (APTRA triesters) and the functionalization of these into suitable building blocks for potential fully conjugated low-affinity fluorescent Ca2+ indicators are described. Georg Th

New substituted derivatives of thiourea. Synthesis1H-NMR and IR spectra

Brǎtulescu, George

, p. 297 - 300 (2007/10/03)

Various new compounds of thiourea were synthesised by reaction of aromatic isothiocyanates with aminoesters. The 1H-NMR and IR spectra were interpreted.

New syntheses of aryl isothiocyanates

Besson, Thierry,Guillard, Jerome,Rees, Charles W.,Thiery, Valerie

, p. 889 - 892 (2007/10/03)

Primary aromatic amines are readily converted into arylimino-1,2,3-dithiazoles 2 and the derived cyanothioformanilides 6, both of which are rapidly cleaved by ethylmagnesium bromide in hot THF to give the corresponding isothiocyanates. The transformation 2→6→ArNCS can be performed as a 'one-pot' operation. The imines 2 are also converted, more slowly, into the isothiocyanates by sodium hydride in hot THF, via the cyanothioformanilides 6. Conversion of the anilides 6 into isothiocyanates is much faster under microwave irradiation in 2,6-lutidine. Mechanisms are proposed for these reactions.

New syntheses of aryl isothiocyanates from N-arylimino-1,2,3-dithiazoles

Besson, Thierry,Guillard, Jerome,Rees, Charles W.,Therisod, Michel

, p. 881 - 882 (2007/10/03)

Treatment of N-arylimino-1,2,3-dithiazoles 2 with ethylmagnesium bromide (2 equiv.) gives the corresponding aryl isothiocyanates 13, providing a very mild two-step conversion of ArNH2 into ArNCS avoiding hazardous reagents; alternatively the iminodithiazoles 2 can be converted into cyanothioformanilides 11 which rapidly give the same isothiocyanates with 1 equiv. of the Grignard reagent.

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