16587-39-6

Usage

Chemical Properties

YELLOW FLUFFY POWDER

InChI:InChI=1/C20H14S/c1-3-9-15(10-4-1)19-17-13-7-8-14-18(17)20(21-19)16-11-5-2-6-12-16/h1-14H

Upstream product

• 1159-86-0 o-dibenzoylbenzene 
• 1035806-30-4 2-benzoylbenzophenone 
• 108-86-1 bromobenzene 
• 88-95-9 Phthaloyl dichloride 
• 162339-29-9 benzene-1,2-dicarbothioic acid di(S-pyridin-2-yl) ester 
• 121-68-6 dithiobenzoic acid 
• 68145-20-0 DL-Phenyl<(thiobenzoyl)thio>essigsaeure 
• 20850-89-9 2,5-diphenyl-1,3-dithiolylium-4-olate 
• 88284-48-4 2-(trimethylsilyl)phenyl trifluoromethanesulfonate 

Downstream Products

• 1159-86-0 o-dibenzoylbenzene 
• 602-55-1 9-phenylanthracene 

Relevant academic research and scientific papers

Visible light-sensitive composition for delivering hydrogen sulfide and use thereof

According to one aspect of the present invention, provided are a composition for delivering H_2S, including a compound, a stereoisomer, a derivative, or a salt thereof, and a singlet oxygen (^1O_2) photosensitizer, and to a pharmaceutical composition, and a method using the same. Accordingly, tunable photosensitivity and a very high ^1O_2 reactivity of an H_2S precursor, in particular, the ability for modifying the wavelength of light irradiation through selection of ^1O_2PS can be provided. Also, a biological utility is provided through intracellular delivery and cytoprotection of H_2S produced under visible light irradiation.

Strain-Promoted 1,3-Dithiolium-4-olates–Alkyne Cycloaddition

Reported here is the reactivity of mesoionic 1,3-dithiolium-4-olates towards strained alkynes, leading to thiophene cycloaddition products. In the process, the potential of these dipoles towards orthogonal reaction with azides, allowing efficient double ligation reactions, was discovered. A versatile process to access benzo[c]thiophenes, in an unprecedented divergent fashion, was developed and provides a new entry to unconventional polyaromatic thiophenes.

Visible light-driven photogeneration of hydrogen sulfide

The combined use of a singlet oxygen photosensitizer and 1,3-diarylisobenzothiophene enables efficient generation of hydrogen sulfide under visible light illumination.

Non-classical S-Heteroacenes with o-Quinoidal Conjugation and Open-Shell Diradical Character

A series of non-classical S-heteroacenes were synthesized and exhibited intriguing physical properties and chemical reactivities that are very different from classical acenes. X-ray crystallographic analyses revealed that all acenothiophene derivatives Ph-AT-1–Ph-AT-3 had an o-quinoidal π-conjugation with large bond-length alternation, whereas the acenodithiophene derivative Ph-ADT-3 easily dimerized or reacted with oxygen to form a peroxy-bridged dimer. The long acenothiophene Ph-AT-4 was also highly reactive. The origin of these unique properties was investigated carefully by both experiments and theoretical calculations. The high reactivity of the long non-classical S-heteroacenes can be explained by their intrinsic open-shell diradical character as well as the o-quinoidal conjugation.

Design of reversible multi-electron redox systems using benzochalcogenophenes containing aryl and/or ferrocenyl fragments

2,3-Disubstituted benzo[b]thiophenes, 1,3-disubstituted benzo[c]thiophenes, and 1,3-disubstituted benzo[c]selenophene have been systematically and selectively synthesized from benzo[b]thiophene or phthaloyl dichloride as a starting material, respectively. Characterization of the molecules was performed by physical and spectroscopic means and X-ray crystallographic analyses. The cyclic voltammograms of the chalcogenophene derivatives containing aryl fragments showed well-defined reversible both anodic and cathodic steps derived from the unusually stable 5π chalcogenophene radical cations and 7π chalcogenophene radical anions. The cyclic voltammograms of the novel chalcogenophene derivatives containing ferrocenyl fragments showed a well-defined reversible cathodic step derived from the unusually stable 7π chalcogenophene radical anions and two distinct reversible anodic steps derived from ferrocenium cations separated from each other by a thiophene-heterocycle. The radical character of several novel 7π chalcogenophene radical anions was measured by ESR spectroscopy.

Oxidation of 1,4-dihydro-1,4-diphenyl-2,3-benzodithiin

1,4-Dihydro-1,4-diphenyl-2,3-benzodithiin (3), synthesized from 1,2-bis(phenylmethyl) benzene (1), was subjected to oxidation to give 1,4-dihydro-1,4-diphenyl-2,3-benzodithiin 2-oxide (4) as a mixture of diastereomers separable by column chromatography. (1R*,2R*,4S*)-1,4-Dihydro-1,4-diphenyl-2,3-benzodithiin 2-oxide (4-meso-1) was obtained preferentially from (1R*,4S*)-1,4-dihydro-1,4-diphenyl-2,3-benzodithiin (3-meso) with m-chloroperbenzoic acid (m-CPBA). The 4-meso-1 stereoisomer afforded an unexpected product 1,3-diphenyl-benzo[c]thiophene (5) upon further oxidation with mCPBA. On the other hand, oxidation of 1,4-dihydro-1,4-diphenyl-2,3-benzodithiin 2-oxides (4-dl and 4-meso), with Oxone gave 1,4-dihydro-1,4-diphenyl-2,3-benzodithiin 2,2-dioxide (7).

A Mild and Simple Synthesis of Benzothiophenes and 4,7-Dihydrobenzothiophenes

The synthesis of 1,3-disubstituted benzothiophenes and 4,7-dihydrobenzothiophenes from o-diacylbenzenes and 4,5-diacylcyclohexenes under very mild conditions is described.