16911-57-2

Upstream product

• 5285-87-0 phenyl thiocyanate 
• 98-91-9 thiobenzoic acid 
• 93-99-2 benzoic acid phenyl ester 
• 1005-56-7 phenylcarbonochloridothioate 
• 121-68-6 dithiobenzoic acid 
• 108-95-2 phenol 
• 98-91-9 thiobenzoic acid 
• 23405-15-4 benzoic acid N-hydroxysuccinimide ester 
• 65-85-0 benzoic acid 
• 100-58-3 phenylmagnesium bromide 
• 3335-22-6 thiobenzoyl chloride 
• 15848-07-4 thiobenzophenone S-oxide 

Downstream Products

• 946-80-5 (benzyloxy)benzene 
• 39203-76-4 N-ethylbenzothioamide 
• 14309-89-8 N-benzyl-benzenecarbothioamide 
• 3113-46-0 2-phenyl-4,5-dihydro-thiazole-4-carboxylic acid methyl ester 
• 2518-12-9 (4R)-2-phenyl-4,5-dihydrothiazole-4-carboxylic acid methyl ester 
• 114467-84-4 α,α-difluorobenzyl phenyl ether 
• 89898-83-9 thiobenzoyl cyanide 
• 3229-70-7 phenolate 

Relevant academic research and scientific papers

Thionoesters: A Native Chemical Ligation-Inspired Approach to Cysteine-Triggered H2S Donors

Native chemical ligation (NCL) is a simple, widely used, and powerful synthetic tool to ligate N-terminal cysteine residues and C-terminal α-thioesters via a thermodynamically stable amide bond. Building on this well-established reactivity, as well as adv

Kinetic study on reactions of O-Y-substituted phenyl thionobenzoates with quinuclidine: Factors governing reactivity and reaction mechanism

Second-order rate constants (kquin) for the reactions of O-Y-substituted phenyl thionobenzoates (3a-3i) with quinuclidine have been measured spectrophotometrically. Comparison of kquin with the rate constants reported previously for the corresponding reactions with benzylamine (kBzNH2) has revealed that quinuclidine is less reactive than benzylamine toward 3a-3i although the former is 2.1 pKa units more basic than the latter. Steric hindrance exerted by quinuclidine has been suggested to be responsible for the decreased reactivity of the tertiary amine. The Bronsted-type plot for the reactions of 3a-3i with quinuclidine is linear with βlg = -0.37. The Hammett plot correlated with σ(Formula presented.) constants exhibits many scattered points (R2 = 0.982). In contrast, the Yukawa-Tsuno plot results in an excellent linear correlation (R2 = 0.9992) with ρY = 0.96 and r = 0.51, indicating that a negative charge develops partially on the O atom of the leaving group. Thus, the reactions of 3a-3i with quinuclidine have been concluded to proceed through a concerted mechanism in which expulsion of the leaving group is advanced only a little in the rate-determining transition state.

Compound embodiments that release H2S by reaction with a reactive compound and methods of making and using the same

Disclosed herein are embodiments of a donor compound that releases H2S by reacting with a reactive compound. The donor compound embodiments described herein can be used to deliver H2S to a subject or a sample and further can be used to administer therapeutic agents. The donor compound embodiments also can facilitate bioconjugation. Methods of making and using the donor compound embodiments also are disclosed.

Ynamide-Mediated Thionoester and Dithioester Syntheses

A novel ynamide-mediated synthesis of thionoesters and dithioesters is described. The selective addition reactions of various monothiocarboxylic acids with ynamide furnish α-thioacyloxyenamides, which undergo transesterification with nucleophilic -OH or -SH species to afford thionoesters and dithioesters, respectively. The broad substrate scope, mild reaction conditions, and excellent yields make this method an attractive synthetic approach to thionoesters and dithioesters.

The Dual Reactivity of 5-S/5-O-Phenyl-1,4,2-oxathiazoles: A Fragmentation Pathway That Affords Nitriles in the Presence of Water

The rearrangement of substituted 1,4,2-oxathiazoles to nitriles in the presence of water is described. Preliminary investigations suggest that the reaction pathway proceeds via a 1,4,2-oxathiazolium intermediate, followed by trapping with water and subsequent decomposition to products. An unprecedented rearrangement of 5-phenyl-1,4,2-oxathiazoles bearing a C5 leaving group to nitriles in the presence of water is described.

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.

Process for producing thionocarboxylic acid ester

The present invention provides a process comprising reacting a halogenated thiocarbonyl compound represented by Formula (1): wherein Ar is an optionally substituted aryl group and X is a halogen atom, with an Grignard compound represented by Formula (2):

Curved Hammett Plot in Alkaline Hydrolysis of O-Aryl Thionobenzoates: Change in Rate-Determining Step versus Ground-State Stabilization

Second-order rate constants have been measured for alkaline hydrolysis of O-aryl thionobenzoates (X-C6H4-CS-OC6H 4-Y) in 80 mol % H2O-20 mol % DMSO at 25.0 ± 0.1 °C. The Hammett plot for the reaction of O-4-nitrophenyl X-substituted thionobenzoates (X-C6H4-CS-OC6H 4-NO2, 1a-e) exhibits a downward curvature. However, a possible traditional explanation in terms of a change in the rate-determining step (RDS) has been considered but rejected. The proposed explanation involves stabilization of the ground-state (GS) through-resonance interaction between the electron-donating substituent X and the thionocarbonyl functionality on the basis of the linear Yukawa-Tsuno plot obtained for the same reaction. The Bronsted-type plot for the reaction of O-aryl thionobenzoates (C 6H5-CS-OC6H4-Y, 2a-i) is linear but exhibits many scattered points with a small βlg, (-0.35). The Hammett plot for the same reaction shows rather poor correlation with σ- constants but much better correlation with σ° constants. The alkaline hydrolysis of O-aryl thionobenzoates (1a-e and 2a-i) has been proposed to proceed through an addition intermediate in which bond formation is the RDS.

Elektroreduktion organischer Verbindungen, 26. Einelektronenreduktion der O-Phenylester aromatischer Thiocarbonsaeuren-eine polarographische und cyclovoltammetrische Untersuchung

Die Halbstufenpotentiale der Elektroreduktion ortho-, meta- und para-substiturierter Thiobenzoesaeure-O-phenylester 1-4 in wasserfreiem Acetonitril werden gemessen.Sie werden mit Hammetts Substituentenkonstanten und mit den UV-VIS-Absorptionsbanden korrel

CARBONYL SULFIDES AS POSSIBLE INTERMEDIATES IN THE PHOTOLYSIS OF OXATHIIRANES

Diphenyl oxathiirane, formed by irradiation of thiobenzophenone S-oxide at 77 K, is photochemically converted into a blue, thermally unstable compound which decomposes at ca 100-110 K (λmax 550 nm, (ε ca 11,000).Lack of change in magnetic susceptibility during the light induced conversion of sulfine to ketone via the oxathiirane and the subsequent blue intermediate implies the absence of triplet and biradical singlet transients.The unknown carbonyl sulfide functionality, R2C=O=S, thereby emerges as a strong candidate for producing the visible absorption.Comparison of the wave function for CH2=S=O and CH2=O=S arising from MNDO limited CI geometry optimizations leads to the conclusion that the carbonyl sulfide structure is best described as a zwitterion rather than as a singlet biradical.The failure to observe cycloaddition products between the blue species and several dipolarophiles is rationlized in terms of a labile carbonyl sulfide intermediate capable of facile sulfur extrusion from a long, weak O-S bond.Finally, the electronic absorption spectra of a series of para-substituted benzaldehyde O-sulfide model system have been calculated with CNDO/S-CI and correlated with the λmax's of the corresponding series of diaryl blue substrates.The sum of the available experimental and theoretical data is consistent with the existence of closed shell carbonyl sulfides as observable, though labile, intermediates from the photolysis of oxathinanes.