645-96-5

Usage

Uses

Used in Chemical Synthesis:
PHENYLSELENOL is used as a starting reagent for the synthesis of monoseleno-substituted 1,3-dienes. It plays a crucial role in creating these specific chemical compounds, which have various applications in the chemical industry.
Used in the Synthesis of Cationic Chalcogenolato-Bridged Diruthenium Complexes:
PHENYLSELENOL is also utilized as a starting reagent in the synthesis of cationic chalcogenolato-bridged diruthenium complexes. These complexes have potential applications in various fields, including catalysis and materials science.
Used in Photochemical Reactions:
In the field of photochemistry, PHENYLSELENOL is used in reactions involving diphenyl diselenide-promoted radical addition to inactivated acetylenes. This process is carried out upon irradiation through Pyrex with a tungsten lamp, highlighting its importance in photochemical synthesis.
Used in Catalysis:
PHENYLSELENOL, generated in situ by the reduction of diphenyl diselenide with tributyltin hydride, is used as a catalyst in stannane-mediated radical chain reactions. This application demonstrates its versatility in facilitating various chemical reactions and improving their efficiency.

Purification Methods

Dissolve it in aqueous N NaOH, acidify this with conc HCl and extract with Et2O, dry over CaCl2, filter, evaporate on a steam bath and distil the residue from a Claisen flask or through a short column collecting the middle fraction, and seal immediately in a glass vial, otherwise the colourless liquid becomes yellow. The alkali insoluble materials consist of diphenylselenide (b 167o/16mm) and diphenyldiselenide, m 63o (from EtOH). TOXIC, use rubber gloves. It has a foul odour. [Foster Org Synth Coll Vol III 771 1955, Beilstein 6 III 1104, 1110, 6 IV 1777.]

InChI:InChI=1/C6H5Se/c7-6-4-2-1-3-5-6/h1-5H

Upstream product

• 109-72-8 n-butyllithium 
• 1132-39-4 diphenylselenide 
• 2179-79-5 phenyl selenocyanate 
• 6996-92-5 benzeneseleninic acid 
• 1666-13-3 diphenyl diselenide 
• 10505-00-7 benzeneselenonic acid 
• 108-86-1 bromobenzene 
• 79-08-3 bromoacetic acid 
• 65910-12-5 (phenylselanyl)acetylene 
• 7101-31-7 dimethyl diselenide 
• 100-52-7 benzaldehyde 
• 688-73-3 tri-n-butyl-tin hydride 
• 7647-01-0 hydrogenchloride 
• 7783-06-4 hydrogen sulfide 

Downstream Products

• 73090-39-8 (phenylseleno)acetaldehyde dimethyl acetal 
• 1666-13-3 diphenyl diselenide 
• 25562-42-9 2-(phenylselanyl)benzoic acid 
• 15905-30-3 β-(phenylseleno)acrylic acid 
• 15642-75-8 (2E)-3-(phenylselanyl)acrylic acid 
• 92463-14-4 o-nitrophenyl phenylselenyl sulfide 
• 4346-64-9 selenoanisole 
• 77151-60-1 (2-nitro-phenyl)-phenyl diselenide 
• 17893-46-8 2-(phenylselanyl)acetic acid 
• 67516-66-9 2,4-dinitrophenyl phenyl selenide 
• 6343-83-5 4-nitrophenyl(phenyl)selenide 
• 76618-48-9 1,3-diphenyl-3-phenylselenyl-propan-1-one 
• 30409-99-5 1,3-diseleno-malonic acid Se,Se'-diphenyl ester 
• 6996-92-5 benzeneseleninic acid 

Relevant academic research and scientific papers

Exploiting structure-activity relationships of QS-21 in the design and synthesis of streamlined saponin vaccine adjuvants

We report the design, synthesis, immunological evaluation, and conformational analysis of new saponin variants as promising vaccine adjuvants. These studies have provided expedient synthetic access to streamlined adjuvant-active saponins and yielded molecular-level insights into saponin conformation that correlated with their in vivo adjuvant activities.

Simultaneous Detection of Glutathione and Hydrogen Polysulfides from Different Emission Channels

Glutathione (GSH) and hydrogen polysulfides (H2Sn) play crucial roles in many physiological processes. To unravel the complicated interrelationship and cellular cross-talk between GSH and H2Sn, the development of single-molecule fluorescent probes that can selectively sense GSH and H2Sn simultaneously from different emission channels is highly desirable. In this report, we have developed the first dual-detection fluorescent probe, ACC-SePh, which responded to GSH with green fluorescence emission, whereas it reacted with H2Sn and emitted blue fluorescence. The probe exhibited excellent selectivity and sensitivity toward GSH and H2Sn over other common reactive sulfur species, such as Cys, Hcy and H2S. Importantly, we also demonstrated that ACC-SePh can be used for dual-channel imaging of endogenous GSH and H2Sn in living RAW264.7 cells.

Synthesis of Seleno Oxindoles via Electrochemical Cyclization of N-arylacrylamides with Diorganyl Diselenides

The tandem cyclization of acrylamide with diselenides facilitated by electrochemical oxidation was successfully developed. This strategy provided an environmentally friendly method for the construction of C?Se bond. A series of seleno oxindoles with pharmacological activity were obtained by using this well-designed tandem cyclization strategy. The in vitro antitumor activity of the compounds was also screened through MTT assay. Results showed that the seleno oxindoles exhibited better antitumor activity than other oxindole derivatives. (Figure presented.).

Click Reaction of Selenols with Isocyanates: Rapid Access to Selenocarbamates as Peroxide-Switchable Reservoir of Thiol-Peroxidase-Like Catalysts

Selenols react with isocyanates under mild catalyst-free conditions to generate selenocarbamates in good yield and with high selectivity over potentially competing nucleophilic additions. The methodology enables the incorporation of a wide variety of functional groups providing access to a broad array of densely functionalised selenocarbamates. In the presence of competing heteroatom-centered nucleophiles, isocyanates selectively couple with selenols. Selenocarbamates exhibited thiol-peroxidase-like properties, enabling the reduction of hydrogen peroxide at the expense of thiols, which are converted into the corresponding disulfides. A series of control experiments suggested that the catalytic mechanism proceeds through a pathway, involving a H2O2-promoted transcarbamoylation reaction leading to a thiocarbamate with concomitant releasing of catalytically active selenolate anions. By undergoing peroxide-driven thiol-selenol exchange, selenocarbamates behave as equivalents of selenolate anions with thiol-peroxidase-like activity. (Figure presented.).

O-(tert-butyl) Se-phenyl selenocarbonate: A convenient, bench-stable and metal-free precursor of benzeneselenol

A study by our laboratory shows that air, light and moisture stable O-(tert-butyl) Se-phenyl selenocarbonate could be employed as a safer, practical and efficient alternative to generate “in situ” benzeneselenol or benzeneselenolate anion under different and transition metal-free conditions. This procedure seems to be of general application since the nucleophilic selenium species obtained can be trapped by electrophiles such as alkyl halides, epoxides and electron-deficient alkenes and alkynes under different reaction conditions.

Lysosomal Reacidification Ameliorates Vinyl Carbamate-Induced Toxicity and Disruption on Lysosomal pH

Ethyl carbamate (EC) is a carcinogen toxicant, commonly found in fermented foods and beverages. The carcinogenic and toxic possibility of EC is thought to be related to its metabolite vinyl carbamate (VC). However, we found interesting mechanisms underlying VC-induced toxicity in this study, which were greatly different from EC. We first conducted a simple synthesis procedure for VC and found that VC possessed higher toxicity but failed to regulate levels of reactive oxygen species, glutathione, and autophagy. Notably, VC treatment resulted in upregulation of lysosomal pH, which was responsible for its cytotoxicity. Cyclic adenosine monophosphate (cAMP) pretreatment could enhance restoration of lysosomal acidity and ameliorate VC-induced damage. Inhibition of protein kinase A and cystic fibrosis transmembrane conductance regulator can block cAMP-induced cytoprotection. Together, our results provided the evidence for novel mechanisms of toxicity and possible protection method under VC exposure, which might give new perspectives on the study of EC-induced toxicity.

Fluorescent probe for differentially detecting GSH and H2Sn (n is more than) through single-wavelength excitation

The invention discloses a fluorescent probe for distinguishing and detecting GSH and H2Sn (n is more than 1) by single excitation, and belongs to the technical field of chemical analysis and detection, wherein the molecular structural formula is defined in the specification. According to the invention, the probe emits green fluorescence after reacting with GSH, and emits red fluorescence after reacting with H2Sn; the probe can realize simultaneous distinguishing detection of GSH and H2Sn (n is more than 1) under single-wavelength excitation, and has the characteristics of good selectivity, high sensitivity, wider pH working range and the like; and the probe can emit red fluorescence in the detection process, so that the excellent properties show that the fluorescent probe has important application value in the fields of environment, biology and the like.

Fluorescent probe for differentially detecting GSH and H2Sn (n >1) through two channels

The invention discloses a fluorescent probe for differentially detecting GSH and H2Sn (n > 1) through two channels, and belongs to the technical field of chemical analysis and detection. The probe hasa molecular structural formula shown in the description. The probe emits green fluorescence after reacting with GSH and emits red fluorescence after reacting with H2Sn. The probe not only can realizesimultaneous distinguishing detection of GSH and H2Sn (n > 1), but also has the characteristics of good selectivity, high sensitivity, relatively wide pH working range and the like. Meanwhile, in thedetection process, the probe can emit red fluorescence, and large Stokes shift is shown. The excellent properties show that the fluorescent probe has important application value in the fields of environment, biology and the like.

Visible-Light-Promoted Selenylative Spirocyclization of Indolyl-ynones toward the Formation of 3-Selenospiroindolenine Anticancer Agents

A metal-free and efficient visible-light-induced spirocyclization of indolyl-ynones with diselenides at room temperature under air atmosphere to prepare 3-selenospiroindolenines in moderate to good yields has been developed. The resulting products were tested for in vitro anticancer activity by MTT assay, and compounds 3 c and 3 e showed potent cancer cell-growth inhibition activities.

Metal-free visible-light induced cyclization/substitution cascade reaction of alkyne-tethered cyclohexadienones and diselenides: Access to 5-hydroxy-3-selenyl-4a,8a-dihydro-2: H -chromen-6(5 H)-ones

A simple and efficient Se-radical triggered cyclization/substitution cascade reaction of alkyne-tethered cyclohexadienones to afford 5-hydroxy-3-selenyl-4a,8a-dihydro-2H-chromen-6(5H)-ones has been developed. This transformation via the 3,5-diselenyl-4a,8a-dihydro-2H-chromen-6(5H)-one intermediate followed by hydrolysis in the presence of CsOAc affords the desired product 3. The resulting products were tested for their in vitro anticancer activity using MTT assay, and compounds 3e and 3q showed potent cancer cell-growth inhibition activities.