2131-60-4

Usage

Uses

Used in Chemical Synthesis:
4-HYDROXYPHENYLISOTHIOCYANATE is used as a key intermediate in the synthesis of various organic compounds, particularly those with potential applications in the field of biochemistry and molecular biology. Its isothiocyanate group allows for the formation of stable conjugates with biological molecules, making it a valuable building block for the development of new compounds.
Used in Fluorescent Probe Development:
In the field of biochemistry and molecular biology, 4-HYDROXYPHENYLISOTHIOCYANATE is used as a precursor for the development of fluorescent probes. These probes are essential tools for studying the structure, function, and interactions of biologically relevant compounds. The compound's ability to form stable conjugates with biomolecules makes it an ideal candidate for the creation of probes that can be used to track and visualize specific biological processes.
Used in the Synthesis of Tricarbocyanine Dyes:
4-HYDROXYPHENYLISOTHIOCYANATE is used as a starting material in the synthesis of 3 functionalized tricarbocyanine dyes. These dyes have potential applications as fluorescent probes for biologically pertinent compounds, allowing researchers to study various biological processes with greater precision and detail.

InChI:InChI=1/C7H5NOS/c9-7-3-1-6(2-4-7)8-5-10/h1-4,9H

Upstream product

• 75-15-0 carbon disulfide 
• 123-30-8 4-amino-phenol 
• 463-71-8 thiophosgene 
• 96989-50-3 di-2-pyridyl thionocarbonate 
• 62812-90-2 triethylamine (4-hydroxyphenyl)carbamodithioate 
• 2926-29-6 Langlois reagent 
• 16420-13-6 N,N-Dimethylthiocarbamoyl chloride 

Downstream Products

• 118726-61-7 trans-crotonic acid-(4-isothiocyanato-phenyl ester) 
• 68448-63-5 methacrylic acid-(4-isothiocyanato-phenyl ester) 
• 730960-14-2 4-allyloxy-phenyl isothiocyanate 
• 104165-81-3 acrylic acid-(4-isothiocyanato-phenyl ester) 
• 21115-11-7 N-(4-hydroxyphenyl)-N'-methylthiourea 
• 121814-40-2 (4-isothiocyanato-phenyl)-(tetra-O-acetyl-ξ-D-glucopyranoside) 
• 21346-21-4 3-(4-hydroxyphenyl)-2-thioxothiazolidin-4-one 
• 108768-40-7 4-isothiocyanatophenyl-4'-n-nonyloxybenzoate 
• 108768-41-8 4-isothiocyanatophenyl-4'-n-decyloxybenzoate 
• 137225-52-6 4-Dodecyloxy-benzoic acid 4-isothiocyanato-phenyl ester 
• 137225-54-8 4-Hexadecyloxy-benzoic acid 4-isothiocyanato-phenyl ester 
• 73552-84-8 (Z)-(4-isothiocyanophenyl)-5-nitro-2-furylvinyl ether 
• 73552-85-9 (E)-(4-isothiocyanophenyl)-5-nitro-2-furylvinyl ether 
• 137225-53-7 4-Tetradecyloxy-benzoic acid 4-isothiocyanato-phenyl ester 

Relevant academic research and scientific papers

First Examples of H2S-Releasing Glycoconjugates: Stereoselective Synthesis and Anticancer Activities

H2S donors are currently emerging as promising therapeutic agents in a wide variety of pathologies, including tumors. Cancer cells are characterized by an enhanced uptake of sugars, such as glucose. Therefore, novel glycoconjugated H2/sub

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.

Synthesis of 2-substituted tetrahydroisoquinolin-6-ols: Potential scaffolds for estrogen receptor modulation and/or microtubule degradation

6-Methoxytetrahydroisoquinoline hydrochloride was converted into four small libraries of substituted ureas, thioureas, sulfonamides and N-aryls, using the tetrahydroisoquinoline nitrogen as the scaffold-linking atom. Some of the compounds were evaluated for their ability to inhibit cell proliferation using the MCF7 (invasive ductal carcinoma) cell line.

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.

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.

Isothiocyanation of amines using the Langlois reagent

The Langlois reagent was found to be effective for the isothiocyanation of primary amines in the presence of copper iodide and diethyl phosphonate.

A novel one-pot synthesis of isothiocyanates and cyanamides from dithiocarbamate salts using environmentally benign reagent tetrapropylammonium tribromide

A highly efficient and simple protocol for the synthesis of isothiocyanates and cyanamides from their respective amines in the presence of a mild, efficient, and non-toxic reagent tetrapropylammonium tribromide is described. High environmental acceptability of the reagents, cost effectiveness and high yields are the important attributes of this methodology.

Multimeric Near IR-MR Contrast Agent for Multimodal in Vivo Imaging

Multiple imaging modalities are often required for in vivo imaging applications that require both high probe sensitivity and excellent spatial and temporal resolution. In particular, MR and optical imaging are an attractive combination that can be used to determine both molecular and anatomical information. Herein, we describe the synthesis and in vivo testing of two multimeric NIR-MR contrast agents that contain three Gd(III) chelates and an IR-783 dye moiety. One agent contains a PEG linker and the other a short alkyl linker. These agents label cells with extraordinary efficacy and can be detected in vivo using both imaging modalities. Biodistribution of the PEGylated agent shows observable fluorescence in xenograft MCF7 tumors and renal clearance by MR imaging. (Figure Presented).

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.

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.]