2486-09-1

Basic information

• Product Name: 2,4-Dinitrophenyl phenyl sulfide
• Synonyms: 2,4-Dinitrophenyl phenyl sulfide
• CAS NO: 2486-09-1
• Molecular Formula: C₁₂H₈N₂O₄S
• Molecular Weight: 276.26792
• Mol File: 2486-09-1.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 2,4-Dinitrophenyl phenyl sulfide(CAS DataBase Reference)
• NIST Chemistry Reference: 2,4-Dinitrophenyl phenyl sulfide(2486-09-1)
• EPA Substance Registry System: 2,4-Dinitrophenyl phenyl sulfide(2486-09-1)

Safety Data

• Hazardous Substances Data: 2486-09-1(Hazardous Substances Data)

Usage

Uses

Used in Organic Chemistry:
2,4-Dinitrophenyl phenyl sulfide is utilized as a reagent for identifying the presence of thiol or sulfide functional groups in various organic compounds. It engages in nucleophilic substitution reactions with thiols, resulting in the formation of 2,4-dinitrophenyl thioethers. These thioethers can be characterized and analyzed using a range of spectroscopic and analytical techniques, making 2,4-Dinitrophenyl phenyl sulfide a valuable tool in the field of organic chemistry.
Used in Pharmaceutical and Agrochemical Synthesis:
Beyond its analytical applications, 2,4-Dinitrophenyl phenyl sulfide also finds use in the synthesis of pharmaceutical and agrochemical products. Its chemical properties make it a suitable intermediate in the production of various compounds that have medicinal or agricultural applications, contributing to the development of new drugs and chemical agents.

Upstream product

• 528-76-7 2,4-dinitrobenzenesulfenyl chloride 
• 71-43-2 benzene 
• 4185-69-7 1-(2,4-dinitrophenyl)-pyridinium chloride 
• 108-98-5 thiophenol 
• 97-00-7 1-chloro-2,4-dinitro-benzene 
• 882-33-7 diphenyldisulfane 
• 930-69-8 sodium thiophenolate 
• 123-91-1 1,4-dioxane 
• 24367-35-9 Phenyl 2-pyridyl disulfide 
• 64-17-5 ethanol 
• 2117-48-8 triphenyl-vinyl stannane 
• 76195-86-3 2,4-dinitrophenylhydrazine hydrochloride 

Downstream Products

• 896-80-0 1-benzenesulfonyl-2,4-dinitro-benzene 
• 19093-39-1 2,4-dinitrophenyl phenyl sulphoxide 
• 6264-74-0 4-(phenylthio)-1,3-phenylenediamine 
• 119-26-6 (2,4-dinitro-phenyl)-hydrazine 

Relevant articles and documents

A phthalimide-based fluorescent probe for thiophenol detection in water samples and living cells with a large Stokes shift

A phthalimide-based fluorescent probe for the detection of thiophenol was developed based on the combination of photo-induced electron transfer (PET) and excited-state intramolecular proton transfer (ESIPT) mechanisms. This probe displays high sensitivity

The construction of an effective far-red fluorescent and colorimetric platform containing a merocyanine core for the specific and visual detection of thiophenol in both aqueous medium and living cells

Thiophenol (PhSH) is toxic to the environment and biological systems although it is an indispensable material in the synthetic processes of chemical products. In this work, we designed and synthesized a malonitrile-based colorimetric and deep-red emission fluorescent dosimeter specifically for thiophenol detection by switching on the intramolecular charge transfer process. The 2,4-dinitrobenzene moiety in the probe could be cleaved by thiophenol, which led to strong deep-red fluorescence increase at 645 nm (50-fold) with a low detection limit of 9 nM. The maximum plateau of emission intensity was reached in about 30 min after the addition of thiophenol. Simultaneously, the presence of thiophenol could result in a prominent color change from orange to blue. Furthermore, the dosimeter could quantitatively sense thiophenol spiked in water samples and successfully visualize thiophenol in living SH-SY5Y cells.

Detection of thiophenol in buffer, in serum, on filter paper strip, and in living cells using a red-emitting amino phenothiazine boranil based fluorescent probe with a large Stokes shift

A novel red-emitting dye, PB-NH2, was synthesized by incorporation of an electron rich phenothiazine moiety to classical boranil dye. PB-NH2 displayed excellent photophysical properties, such as long emission wavelength, large Stokes

An acetophenothiazine-based fluorescence probe for multi-channel imaging of thiophenol with a large Stokes shift

By integrating a phenothiazine moiety as an electron donor and an acetyl moiety as the electron acceptor, a novel D-π-A system dye, PTZAc, with a broadband emission spectrum (the full width at half maxima can reach to 123 nm) and a large Stokes shift (up to 217 nm) was developed. Based on this ideal platform, a novel 2,4-dinitrophenyl-ether type fluorescent probe, PTZAc-1, for thiophenol detection was fabricated. Upon addition of thiophenol, PTZAc-1 exhibited drastic fluorescence enhancement (over 26 folds intensity enhancement at 590 nm) and the corresponding detection limit was calculated to be 1.03 μM. Significantly, the application of PTZAc-1 for intracellular thiophenol imaging in a multi-channel manner was successfully demonstrated in living RAW 264.7 cells.

A red-to-near-infrared fluorescent probe for the detection of thiophenol based on a novel hydroxylflavone-quinoline-amino molecular system with large Stokes shift

In this work, we synthesized a novel long-wavelength-emitting fluorophore FQ-OH based on a novel designed hydroxylflavone-quinoline-amino molecular system with both intramolecular charge transfer (ICT) and excited-state intramolecular proton transfer (ESIPT) process, enabling FQ-OH with strong fluorescence in a wide range of 550–800 nm, covering red-to-near-infrared emission region and large stokes shift as much as 162 nm. Due to the promising spectra property, FQ-OH was then fabricated into a red-to-near-infrared fluorescent probe FQ-DNP for the selective detection of thiophenol via aromatic nucleophilic substitution (SNAr) reaction mechanism. Spectra assays in the solution demonstrated that FQ-DNP displayed prominent turn-on fluorescence response to thiophenol in 550–800 nm with emission peak at 627 nm, excellent selectivity, and exceptional sensitivity (detection limit as low as 7.2 nM). In addition, thiophenol in vapor form could be detected by FQ-DNP coated test papers enabling naked eye detection. Moreover, FQ-DNP was utilized for detecting thiophenol in environmental samples and showed great recovery results. Furthermore, biological application of FQ-DNP in living cells through cell imaging study demonstrated apparent intracellular fluorescence enhancement before/after thiophenol addition.

Simultaneous Discrimination of Cysteine, Homocysteine, Glutathione, and H2S in Living Cells through a Multisignal Combination Strategy

Biothiols are essential reactive sulfur species (RSS), which play crucial roles in various critical physiological activities. To clarify their complex correlations in signal transduction and metabolism pathways, methods to distinguish H2S, cyst

2,4-Dinitrobenzenesulfonyl fluoresceins as fluorescent alternatives to Ellman's reagent in thiol-quantification enzyme assays

(Chemical Equation Presented) Fluorescent sensor for thiols: Deprotection of nonfluorescent 1 by thiols (R′SH) proceeds rapidly and near-quantitatively in aqueous solution (pH 7.4) to produce highly fluorescent 2. Assays performed in the presence of 1 provide a rapid and simple method for the determination of inhibitory constants for inhibitors such as donepezil toward acetyl- and butyrylcholinesterases.

An Iodide-Mediated Transition-Metal-Free Strategy towards Unsymmetrical Diaryl Sulfides via Arylhydrazines and Thiols

A mild, scalable iodine-mediated oxidative cross-coupling reaction of arylhydrazines and thiols for construction of thioethers (sulfides) in the absence of any transition metals or photocatalysts is disclosed. A variety of unsymmetrical diaryl sulfides with broad substrate scope both on thiols and hydrazines were synthesized in high yields in water at room temperature. Furthermore, to demonstrate the utility of the protocol, the above C-S bond formation was applied in the synthesis of the key structure of vortioxetine as an antidepressant drug. The gram-scale outcome also added to the potential utility of this protocol.

Short Wavelength Inner Filter Technique (SWIFT) in Designing Reactive Fluorescent Molecular Probes

Here, we present a conceptually novel and experimentally straightforward technique for selective analyte detection that uses a combination of commercial fluorophores and simple chemicals. The technique utilizes the well-known inner filter effect (IFE); however, the fluorophore's excitation is performed at wavelengths significantly shorter than its absorption maximum. In the presence of the analyte, the "filter" appears or disappears at the excitation wavelength resulting in the fluorescence turning OFF or ON, respectively. Unlike common probes, our technique allows real-time monitoring of a fluorophore's stability as well as its recycling. We further demonstrate the applicability of this technique in continuing analyte detection as well as vapor analysis.

A rapid and visible colorimetric fluorescent probe for benzenethiol flavor detection

Benzenethiols are a class of flavoring ingredients used in the food, pharmaceutical, cosmetics and chemical industries. A rapid and visible colorimetric fluorescent probe was developed for the detection of benzenethiol flavors. It provides rapid quantitative detection of benzenethiols at low levels, down to a limit of 10 nM. Test paper containing the probe changes color according to benzenethiol concentration (from colorless to pink, visible with the naked eye). The probe was also successfully used to test benzenethiol concentrations in real food samples. This study demonstrates that this novel probe can be employed as a benzenethiol testing tool.