13509-34-7

Usage

InChI:InChI=1/C13H10O2S/c16-13(14-11-7-3-1-4-8-11)15-12-9-5-2-6-10-12/h1-10H

Upstream product

• 500312-07-2 O-(2-naphthyl) O-phenyl thiocarbonate 
• 139-02-6 sodium phenoxide 
• 1005-56-7 phenylcarbonochloridothioate 
• 108-95-2 phenol 
• 463-71-8 thiophosgene 
• 75-15-0 carbon disulfide 
• 340-04-5 1-phenyl-2,2,2-trifluoromethylethanol 
• 56-23-5 tetrachloromethane 
• 7732-18-5 water 
• 5070-14-4 bis(4-nitrophenyl) thionocarbonate 
• 579516-45-3 O-phenyl O-(2,4-dinitrophenyl) thiocarbonate 
• 1443430-40-7 3-nitrophenyl 4-cyanophenyl thionocarbonate 
• 3229-70-7 phenolate 
• 370104-80-6 O‐(4‐cyanophenyl) O‐(4‐nitrophenyl) thiocarbonate 

Downstream Products

• 3898-08-6 1,1-diphenylthiourea 
• 108-95-2 phenol 
• 13509-33-6 O,S-di(phenyl) thiocarbonate 
• 19547-44-5 5,5-diphenoxy-3-phenyl-1,4,2-oxathiazole 
• 36783-76-3 2-(4-nitro-phenyl)-5-phenoxy-4-phenyl-thiazole 
• 102-09-0 bis(phenyl) carbonate 
• 116858-41-4 thiocarbonic acid O,O'-bis-(4-bromo-phenyl ester) 
• 352-93-2 diethyl sulphide 
• 124-38-9 carbon dioxide 
• 17356-08-0 thiourea 
• 18795-64-7 (CF₃)2CCSSC(OC₆H₅)2 
• 3229-70-7 phenolate 
• 1579249-10-7 3-β-phenethyl-5,5-diphenoxy-1,4,2-oxathiazole 
• 1579249-09-4 3-(4-methoxyphenyl)-5,5-diphenoxy-1,4,2-oxathiazole 

Relevant academic research and scientific papers

Short Total Synthesis of [15N5]-Cylindrospermopsins from 15NH4Cl Enables Precise Quantification of Freshwater Cyanobacterial Contamination

Fresh water cyanobacterial algal blooms represent a major health risk because these organisms produce cylindrospermopsin, a toxic, structurally complex, zwitterionic uracil-guanidine alkaloid recognized by the EPA as a dangerous drinking water contaminant. At present, the ability to detect and quantify the presence of cylindrospermospin in water samples is severely hampered by the lack of an isotopically labeled standard for analytical mass spectrometry. Herein, we present a concise, scaled total synthesis of 15N cylindrospermosin from 15N ammonium chloride, which leverages a unique stereoselective intramolecular double conjugate addition step to assemble the tricyclic guanidine core. In addition to providing the first pure isotopically labeled probe for precise quantification of this potent biotoxin in fresh water sources, our results demonstrate how unique constraints associated with isotope incorporation compel novel solutions to synthesis design.

Kinetic Control over CdS Nanocrystal Nucleation Using a Library of Thiocarbonates, Thiocarbamates, and Thioureas

We report a family of substituted thiocarbonates, thiocarbamates, and thioureas and their reaction with cadmium oleate at 180-240 °C to form zincblende CdS nanocrystals (d = 2.2-5.9 nm). To monitor the kinetics of CdS formation with UV-vis spectroscopy, t

An Unconventional Mechanistic Insight into SCF3 Formation from Difluorocarbene: Preparation of 18F-Labeled α-SCF3 Carbonyl Compounds

Trifluoromethylthiolation by sulfuration of difluorocarbene with elemental sulfur is described for the first time, which overrides long-standing trifluoromethyl anion-based theory. Mechanistic elucidation reveals an unprecedented chemical process for the

Investigations of the Thermal Responsiveness of 1,4,2-Oxathiazoles

The first systematic study of the thermal rearrangement/fragmentation of 5,5-disubstituted 1,4,2-oxathiazoles into isothiocyanates is reported. Structure-activity relationships reveal that the choice of substituent at the 5-position of the 1,4,2-oxathiazoles is the predominant factor to influence the ease of fragmentation.

Kinetic and theoretical study on nucleofugality in the phenolysis of 3-nitrophenyl and 4-nitrophenyl 4-cyanophenyl thionocarbonates

The phenolysis of 3-nitrophenyl 4-cyanophenyl thionocarbonate (1) and 4-nitrophenyl 4-cyanophenyl thionocarbonate (2) are subjected to a kinetic investigation in order to evaluate the nucleofugality of the corresponding leaving groups. For the reaction of 2 only 4-nitrophenoxide is obtained as leaving group. For the reaction of 1 the nucleofugality ratio 3-nitrophenoxide/4-cyanophenoxide is 1/3 from the corresponding T- intermediate. Theoretical calculations confirm the experimental results. From these results it can be concluded that the non-leaving group affects the nucleofugality ratio.

Synthesis of isothiocyanates by reaction of amines with phenyl chlorothionoformate via one-pot or two-step process

A facile and efficient synthesis of isothiocyanates from amines is described. This method involves the reaction of amines with phenyl chlorothionoformate in the presence of solid sodium hydroxide by either a one-pot process or a two-step approach. The one-pot process is useful for preparing alkyl and electron-rich aryl isothiocyanates, whereas the two-step approach is more versatile, working very well not only for alkyl and electron-rich aryl isothiocyanates, but also for highly electron-deficient aryl and heterocyclic isothiocyanates. Georg Thieme Verlag Stuttgart, New York.

Radical OfC transposition: A metal-free process for conversion of phenols into benzoates and benzamides

We report a metal-free procedure for transformation of phenols into esters and amides of benzoic acids via a new radical cascade. Diaryl thiocarbonates and thiocarbamates, available in a single high-yielding step from phenols, selectively add silyl radicals at the sulfur atom of the CdS moiety. This addition step, analogous to the first step of the Barton-McCombie reaction, produces a carbon radical which undergoes 1,2 OfC transposition through an O-neophyl rearrangement. The usually unfavorable equilibrium in the reversible rearrangement step is shifted forward via a highly exothermic C-S bond scission in the O-centered radical, which furnishes the final benzoic ester or benzamide product. The metal-free preparation of benzoic acid derivatives from phenols provides a potentially useful alternative to metal-catalyzed carbonylation of aryl triflates.

DIRECT CONVERSION OF PHENOLS INTO AMIDES AND ESTERS OF BENZOIC ACID

A method is provided for the preparation of an aromatic carboxylic acid aryl ester or an N-aryl aromatic carboxamide. The method comprises contacting an O,O-diaryl thiocarbonate or an O-aryl-N-aryl thiocarbamate with a reactant that regioselectively reacts with sulfur, which contact causes an O-neophyl rearrangement, thereby forming either the aromatic carboxylic acid aryl ester or the N-aryl aromatic carboxamide, respectively.

Alkaline hydrolysis of Y-substituted phenyl phenyl thionocarbonates: Effect of changing electrophilic center from C=O to C=S on reactivity and mechanism

Second-order rate constants (kOH-) have been measured spectrophotometrically for reactions of Y-substituted phenyl phenyl thionocarbonates (4a-i) with OH- in 80 mol % H2O/20 mol % DMSO at 25.0 ± 0.1 °C. The ksu

Radical 1,2-o→c transposition for conversion of phenols into benzoates by o-neophyl rearrangement/fragmentation cascade

Figure Presented Radical merry-go-round! Diaryl thiocarbonates, available in a single step from phenols, can be directly transformed into benzoates by a new radical cascade that transposes O and C atoms at the aromatic core. The cascade bypasses the common Barton McCombie fragmentation in favor of the usually unfavorable O-neophyl rearrangement, which is rendered irreversible and efficient by a highly exothermic C-S bond scission in the O-centered radical (see scheme; FG = functional group).