3694-57-3

Usage

Uses

Used in Pharmaceutical Industry:
4-Methoxybenzyl isothiocyanate is used as a pharmaceutical intermediate for the synthesis of different drugs. Its unique chemical properties make it a valuable component in the development of new medications, contributing to the advancement of pharmaceutical research and drug discovery.
As a chemical intermediate, 4-Methoxybenzyl isothiocyanate plays a significant role in the production of various pharmaceutical compounds. Its versatility and reactivity in chemical reactions enable the creation of a wide range of therapeutic agents, addressing diverse medical needs and conditions.

InChI:InChI=1/C9H9NOS/c1-11-9-4-2-8(3-5-9)6-10-7-12/h2-5H,6H2,1H3

Upstream product

• 499-27-4 glucoaubrietin 
• 540-72-7 sodium thiocyanide 
• 46122-80-9 (4-methoxybenzyl)dimethylsulfonium 
• 75-15-0 carbon disulfide 
• 2393-23-9 4-methoxy-benzylamine 
• 18494-82-1 2-(4-methoxy-benzyloxy)-tetrahydro-pyran 
• 1147550-11-5 ammonium thiocyanate 
• 14629-56-2 trimethyl(4-methoxybenzyloxy)silane 
• 105-13-5 4-Methoxybenzyl alcohol 
• 163276-49-1 1-thiocyanatopyrrolidine-2,5-dione 
• 557-42-6 zinc(II) thiocyanate 
• 2746-25-0 p-Methoxybenzyl bromide 
• 333-20-0 potassium thioacyanate 
• 592-85-8 mercury(II) thiocyanate 

Downstream Products

• 22313-70-8 1,3-bis(4-methoxyphenylmethyl)thiourea 
• 134593-75-2 C₂₁H₂₇NO₄S 
• 158631-97-1 (3aS,3bS,6aR,7R,7aS)-7-Benzyloxymethyl-7-iodo-6-(4-methoxy-benzyl)-2,2-dimethyl-hexahydro-1,3,4-trioxa-6-aza-cyclopenta[a]pentalen-5-one 
• 214400-60-9 1-{3-tert-Butyl-5-[3-(4-methoxy-benzyl)-thioureidomethyl]-benzyl}-3-(4-methoxy-benzyl)-thiourea 
• 915720-81-9 5-(4-methoxy-benzylamino)-thiazole-4-carboxylic acid methyl ester 
• 401907-89-9 1-(furan-2-ylmethyl)-3-(4-methoxybenzyl)thiourea 
• 874288-81-0 5-(4-methoxy-benzylamino)-thiazole-4-carboxylic acid ethyl ester 
• 1356003-69-4 (4Z)-1-(4-methoxybenzyl)-4-(4-methoxybenzylidene)-2-(4-methoxyphenyl)-4,5-dihydro-1H-imidazol-5-one 
• 1356003-71-8 (5Z)-3-(4-methoxybenzyl)-5-(4-methoxybenzylidene)-2-thiohydantoin 
• 287918-21-2 3-(4-methoxybenzyl)-2-thioxoimidazolidin-4-one 
• 1359941-57-3 4-(4-methoxybenzyl)-1-{[(4-phenyl-5-(pyridin-3-yl)-4H-1,2,4-triazol-3-yl)sulfanyl]acetyl} thiosemicarbazide 
• 105-13-5 4-Methoxybenzyl alcohol 

Relevant academic research and scientific papers

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.

HIGH-PURITY ISOTHIOCYANATE COMPOUND PREPARATION METHOD FOR INDUSTRIAL PRODUCTION

The present invention provides a high-purity isothiocyanate compound preparation method for industrial production. Specifically, in the method, organic amine and CS2 are used as raw materials to prepare the thiocarbamate, and then desulfurization is carried out, and the high-purity isothiocyanate compound is obtained by using purification, post-processing and other methods. The method in the present invention is suitable for industrial production, is simple in the post-processing, has a high yield rate, and allows the product to have a high purity, and is suitable for the production of the isothiocyanate compound in the pharmaceutical industry.

PREPARATION METHOD FOR AND INTERMEDIATE OF PYRROLO SIX-MEMBERED HETEROAROMATIC RING DERIVATIVE

Disclosed are an intermediate of a pyrrolo six-membered heteroaromatic ring derivative as a JAK inhibitor and a preparation method therefor, and a method for preparing a pyrrolo six-membered heteroaromatic ring derivative using the intermediate. The metho

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.

PREPARATION METHOD FOR PYRROLE SIX-MEMBERED HETEROARYL RING DERIVATIVE AND INTERMEDIATE THEREOF

The present invention relates to preparation method for pyrrole six-membered heteroaryl ring derivative and intermediate thereof. Specifically, the present invention relates to a preparation method for pyrrole six-membered heteroaryl ring derivative, inte

Discovery of Inhibitor of Wnt Production 2 (IWP-2) and Related Compounds As Selective ATP-Competitive Inhibitors of Casein Kinase 1 (CK1) δ/?

Inhibitors of Wnt production (IWPs) are known antagonists of the Wnt pathway, targeting the membrane-bound O-acyltransferase porcupine (Porcn) and thus preventing a crucial Wnt ligand palmitoylation. Since IWPs show structural similarities to benzimidazol

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

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.

Microwave-assisted synthesis of alkyl thiocyanates

Microwave irradiation accelerated the reaction of t-alkyl, allyl, and benzyl halides with Zn(SCN)2 to afford thiocyanates in excellent yields and high selectivity with the formation of isothiocyanates only in minor proportions. Because thiocyanates are stable intermediates to thiols, the method also affords facile access to corresponding thiols.

Design, synthesis, and evaluation of pH-dependent hydrolyzable emetine analogues as treatment for prostate cancer

The N-2′ position of the natural product emetine has been derivatized to thiourea, urea, sulfonamide, dithiocarbamate, carbamate, and pH responsive hydrolyzable amide analogues. In vitro studies of these analogues in PC3 and LNCaP prostate cancer cell lines showed that the analogues are generally less cytotoxic (average IC50 ranging from 0.079 to 10 μM) than emetine (IC50 ranging from 0.0237 to 0.0329 μM). The pH sensitive sodium dithiocarbamate salt 13 and the amide analogues 21, 22, 26 (obtained from maleic and citraconic anhydrides) showed the most promise as acid-activatable prodrugs under mildly acidic conditions found in the cancer microenvironment. These prodrugs released 12-83% of emetine at pH 6.5 and 41-95% emetine at pH 5.5. Compounds 13 and 26 were further shown to exhibit increased cytotoxicity in PC3 cell culture medium that was already below pH 7.0 at the time of treatment.