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Cas Database

108-98-5

108-98-5

Identification

  • Product Name:Thiophenol

  • CAS Number: 108-98-5

  • EINECS:203-635-3

  • Molecular Weight:110.18

  • Molecular Formula: C6H6S

  • HS Code:2930.90

  • Mol File:108-98-5.mol

Synonyms:Mercaptobenzene;NSC 6953;Phenol, thio-;Phenyl mercaptan;Phenylthiol;Benzenethiol;

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Safety information and MSDS view more

  • Pictogram(s):ToxicTVeryT+

  • Hazard Codes:T+,T

  • Signal Word:No signal word.

  • Hazard Statement:H226 Flammable liquid and vapourH300 Fatal if swallowed H310 Fatal in contact with skin H315 Causes skin irritation H319 Causes serious eye irritation H330 Fatal if inhaled H335 May cause respiratory irritation H361 Suspected of damaging fertility or the unborn child H372 Causes damage to organs through prolonged or repeated exposure H400 Very toxic to aquatic life H410 Very toxic to aquatic life with long lasting effects

  • First-aid measures: General adviceConsult a physician. Show this safety data sheet to the doctor in attendance.If inhaled Fresh air, rest. Refer for medical attention. In case of skin contact Remove contaminated clothes. Rinse skin with plenty of water or shower. Refer for medical attention . In case of eye contact First rinse with plenty of water for several minutes (remove contact lenses if easily possible), then refer for medical attention. If swallowed Rinse mouth. Refer for medical attention . Marked potential for causing eye changes. May cause death (EPA, 1998) Immediate first aid: Ensure that adequate decontamination has been carried out. If patient is not breathing, start artificial respiration, preferably with a demand-valve resuscitator, bag-valve-mask device, or pocket mask, as trained. Perform CPR as necessary. Immediately flush contaminated eyes with gently flowing water. Do not induce vomiting. If vomiting occurs, lean patient forward or place on left side (head-down position, if possible) to maintain an open airway and prevent aspiration. Keep patient quiet and maintain normal body temperature. Obtain medical attention. /Sulfur and related compounds/

  • Fire-fighting measures: Suitable extinguishing media If material on fire or involved in fire: Do not extinguish fire unless flow can be stopped. Use water in flooding quantities as fog. Cool all affected containers with flooding quantities of water. Apply water from as far a distance as possible. Solid streams of water may be ineffective. Use foam, dry chemical, or carbon dioxide. /Phenyl mercaptan/ When heated to decomposition or on contact with acids, it emits toxic fumes of sulfur oxides. May be ignited by heat, sparks or flames. Container may explode in heat of fire. Vapor explosion and poison hazard indoors, outdoors or in sewers. Unstable, oxidizes in air. Avoid contact with acids. (EPA, 1998) Wear self-contained breathing apparatus for firefighting if necessary.

  • Accidental release measures: Use personal protective equipment. Avoid dust formation. Avoid breathing vapours, mist or gas. Ensure adequate ventilation. Evacuate personnel to safe areas. Avoid breathing dust. For personal protection see section 8. Personal protection: chemical protection suit including self-contained breathing apparatus. Collect leaking and spilled liquid in sealable containers as far as possible. Absorb remaining liquid in sand or inert absorbent. Then store and dispose of according to local regulations. Environmental considerations: Land spill: Dig a pit, pond, lagoon, holding area to contain liquid or solid material. /SRP: If time permits, pits, ponds, lagoons, soak holes, or holding areas should be sealed with an impermeable flexible membrane liner./ Dike surface flow using soil, sand bags, foamed polyurethane, or foamed concrete. Absorb bulk liquid with fly ash, cement powder, or commercial sorbents. /Phenyl mercaptan/

  • Handling and storage: Avoid contact with skin and eyes. Avoid formation of dust and aerosols. Avoid exposure - obtain special instructions before use.Provide appropriate exhaust ventilation at places where dust is formed. For precautions see section 2.2. Separated from strong oxidants, strong acids and food and feedstuffs.Conditions for safe storage, including any incompatibilities: Store in cool place. Keep container tightly closed in a dry and well-ventilated place. Containers which are opened must be carefully resealed and kept upright to prevent leakage.

  • Exposure controls/personal protection:Occupational Exposure limit valuesRecommended Exposure Limit: 15 Minute Ceiling Value: 0.1 ppm (0.5 mg/cu m).Biological limit values Handle in accordance with good industrial hygiene and safety practice. Wash hands before breaks and at the end of workday. Eye/face protection Safety glasses with side-shields conforming to EN166. Use equipment for eye protection tested and approved under appropriate government standards such as NIOSH (US) or EN 166(EU). Skin protection Wear impervious clothing. The type of protective equipment must be selected according to the concentration and amount of the dangerous substance at the specific workplace. Handle with gloves. Gloves must be inspected prior to use. Use proper glove removal technique(without touching glove's outer surface) to avoid skin contact with this product. Dispose of contaminated gloves after use in accordance with applicable laws and good laboratory practices. Wash and dry hands. The selected protective gloves have to satisfy the specifications of EU Directive 89/686/EEC and the standard EN 374 derived from it. Respiratory protection Wear dust mask when handling large quantities. Thermal hazards

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Relevant articles and documentsAll total 289 Articles be found

The Selective Deprotection of Thioesters Using Titanium(IV) Chloride/Zinc

Jin, Chung Keun,Jeong, Hyung Jae,Kim, Min Kyu,Kim, Ju Young,Yoon, Yong-Jin,Lee, Sang-Gyeong

, p. 1956 - 1958 (2001)

A new method for deprotection of thioesters using TiCl4/Zn at 0-25 deg C is described. The procedure chemoselectively cleaves the S-CO bond in thioesters in the presence of other carbonyl functional groups and other protecting groups to cleanly produce thiols.

Synthesis of 14-aryl-14H-7-thiadibenzo[a,j]anthracene

Khoramabadi-zad, Ahmad,Akbari, Safar-Ali,Shiri, Azam,Veisi, Hojat

, p. 2443 - 2449 (2005)

Preparation methods of dibenzoxanthene derivatives are surveyed alongside the synthesis of some of the titled compounds, which are the sulfur analogues of dibenzoxanthenes. Our new procedure for the conversion of phenols to thiophenols was used to prove the structure of such sulfur analogues. Copyright Taylor & Francis Inc.

Farnesyl Pyrophosphate Synthase as a Target for Drug Development: Discovery of Natural-Product-Derived Inhibitors and Their Activity in Pancreatic Cancer Cells

Han, Shuai,Li, Xin,Xia, Yun,Yu, Zhengsen,Cai, Ningning,Malwal, Satish R.,Han, Xu,Oldfield, Eric,Zhang, Yonghui

, p. 10867 - 10896 (2019)

Human farnesyl pyrophosphate synthase (Homo sapiens FPPS, HsFPPS) is a target for treating bone resorption diseases and some cancers. HsFPPS is potently inhibited by bisphosphonates, but due to poor cell penetration and distribution in soft tissue, there is currently interest in the development of non-bisphosphonate inhibitors as cancer therapeutics. Here, we report the discovery and development of HsFPPS inhibitors based on the phenolic diterpene carnosic acid (CA), an antimicrobial found in rosemary and sage, which showed better cellular anticancer activities than the bisphosphonate drug zoledronate in pancreatic cancer cell lines, as well as an HsFPPS-dependent mechanism of action. Hit-to-lead optimization of CA improved HsFPPS inhibition by >100-fold. A slow dissociation inhibition pattern and a noncompetitive allosteric binding mode were found, and cellular mechanism-of-action studies showed that these inhibitors inhibit tumor cell growth primarily by inhibiting HsFPPS, leading to downregulation of Ras prenylation and cell apoptosis. The discovery of this series of compounds together with proof-of-mechanism in pancreatic cancer cells may pave the way for targeting HsFPPS in soft tissue cancers using natural-product-derived inhibitors.

Palladium-Catalyzed Double Borylation of Diaryl Sulfoxides with Diboron

Saito, Hayate,Nogi, Keisuke,Yorimitsu, Hideki

, p. 4769 - 4774 (2017)

Borylation of the C-S bond of diaryl sulfoxides with bis(pinacolato)diboron (B 2 pin 2) is accomplished by means of a phosphine-ligated palladium catalyst and LiN(SiMe 3) 2 as a base. Both of the aryl rings of the diaryl sulfoxides are converted into borylated products.

Radiation-chemical transformation of elemental sulfur in the presence of ionic liquids

Tarasova,Zanin

, p. 46 - 49 (2015)

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THERMAL DECOMPOSITION OF DIPHENYL DISULFIDE IN A HYDROGEN SULFIDE ATMOSPHERE

Voronkov, M. G.,Deryagina, E. N.,Papernaya, L. K.

, p. 1905 - 1906 (1982)

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-

Mustafa et al.

, p. 310 (1967)

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A mild and practical deprotection method for benzyl thioethers

Akao, Atsushi,Nonoyama, Nobuaki,Yasuda, Nobuyoshi

, p. 5337 - 5340 (2006)

A highly effective and mild deprotection method was developed for benzyl thioethers using dibutylmagnesium in the presence of a catalytic amount of titanocene dichloride. This methodology is applicable to both aromatic and aliphatic benzyl thioethers.

Kinetics and Mechanism of the Aminolysis of O-Ethyl S-Aryl Ditihiocarbonates

Cabrera, Mauricio,Castro, Enrique A.,Salas, Mirtha,Santos, Jose G.,Sepulveda, Patricia

, p. 5324 - 5328 (1991)

The reactions of O-ethyl S-phenyl dithiocarbonate (1) and O-ethyl S-(p-nitrophenyl dithiocarbonate (2) with a series of secondary alicyclic amines, namely, piperidine, piperazine, 1-(β-hydroxyethyl)piperazine, morpholine, 1-formylpiperazine, and (with 2 only) piperazinium ion, are subject to a kinetic study at several pH values.The reaction leads to the corresponding thiocarbamates and thiophenols (measured as thiophenoxide ion by UV-vis spectrophotometry).Pseudo-first-order rate coefficients (kobsd) are found throughout (amine excess).The kinetics are first order in amine for the reactions of 2.The plots of kobsd vs for the reaction of 1, except with 1-formylpiperazine, are linear, but near the origin they are curved, showing a more complex rate equation.The reaction of 1 with 1-formylpiperazine shows a second-order dependence on the amine.No dependence on pH of the second-order rate constant values is observed.The findings are well-accommodated by a mechanistic model involving reversible nucleophilic attack on the thiocarbonyl group, two tetrahedral intermediates, 3 and 4, and a deprotonation step.The Bronsted-type plots obtained are linear (β1 = 0.22) for the reaction of 1 and curved for 2 (β1 = 0.2 and β2 = 0.8).The Bronsted-type plot obtained with the rate constants for amine expulsion from 3 is linear with β-1 = -0.67 and -0.54 for the reactions of 1 and 2, respectively.

First synthesis and characterization of vinylselenols and vinyltellurols

Guillemin, Jean-Claude,Bouayad, Asmae,Vijaykumar, Dange

, p. 1163 - 1164 (2000)

Vinylselenols and vinyltellurols have been prepared by slow addition of tributyltin hydride to the corresponding divinyldiselenide or divinylditelluride in tetraglyme.

Facile Conversions of Aliphatic Sulfonic Acids, Sulfinic Acids, Thiols, Sulfonates, Thiosulfonates, and Disulfides to the Corresponding Alkyl Iodides by Triphenylphosphine/Iodine

Oae, Shigeru,Togo, Hideo

, p. 371 - 373 (1981)

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Visible-Light-Induced Difluoropropargylation Reaction with Benzothiazoline as a Reductant

Chen, Jingzhi,Huang, Wenhao,Li, Ying,Cheng, Xu

, p. 1466 - 1472 (2018)

The difluoropropargyl group is a useful moiety for biological applications such as in vivo click chemistry for molecular imaging techniques. Silyl-protected bromodifluoropropyne is an important difluoropropargylation reagent with previously unexplored radical reactivity. Herein, we report visible-light-induced thiyl-radical-catalyzed hydrodifluoropropargylation reactions between silyl-protected bromodifluoropropyne and alkenes in the presence of benzothiazoline as a critical reductant. (Figure presented.).

Pd-PVP-Fe (palladium-poly(N-vinylpyrrolidone)-iron) catalyzed S-arylation of thiols with aryl halides in aqueous media

Ghaderi-Shekhi Abadi, Parvaneh,Rafiee, Ezzat,Joshaghani, Mohammad

, p. 162 - 170 (2016)

Pd-PVP-Fe (palladium-poly(N-vinylpyrrolidone)-iron) nano catalyst catalyzes selective C–S cross-coupling (S-arylation) reactions of thiols with aryl halides and avoids the formation of S–S (disulfide) homocoupling byproducts. The reactions were carried out in aqueous media using only 0.23?mol% palladium with high selectivity and short reaction time. The effects of the Pd0and Fe0moieties on the C–S cross-coupling reaction mechanism, yield, and selectivity were investigated. The yield and selectivity can be controlled by adjusting the order of adding the reactants and catalyst into the reaction medium. The X-ray photoelectron spectroscopy (XPS), scanning electron microscopy (SEM), electron backscatter diffraction (EBSD) microscopy, energy dispersive X-ray (EDX) spectroscopy, and thermal gravimetric analysis (TGA) tools were used to characterize the catalyst. The C–S cross-coupling reaction process could be repeated up to six times without losing effectiveness. The metals leaching of Pd-PVP-Fe nanocatalyst after reusing cycles were investigated by atomic absorption spectroscopic (AAS) and EDX spectroscopy. The nature of Pd metal after the first run of the C–S cross-coupling reaction was studied by UV–vis spectrophotometry. The morphology of bimetallic nanocatalyst after the first run of the C–S cross-coupling reaction was investigated by SEM, EBSD, and EDX microscopy.

-

Lavanish

, p. 3847 (1973)

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GAS-PHASE PYROLYSIS OF BIS(PHENYLTHIO)ACETYLENE

Voronkov, M. G.,Deryagina, E. N.,Sukhomazova, E. N.,Mirskova, A. N.,Seredkina, S. G.

, (1983)

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Catalytic Function of a 3,3'-Tetramethylene-bridged 4-Methylthiazolium Salt in the Reductive Cleavage of the Sulphur-Sulphur Bond of Disulphides with o-Methylbenzaldehyde and Bases

Inoue, Hiroo,Tamura, Shigeo

, p. 858 - 859 (1986)

A 3,3'-tetramethylene-bridged 4-methylthiazolium salt, in methanol containing o-methylbenzaldehyde and triethylamine or 1,5-diazabicycloundec-5-ene, catalyses the reduction of diphenyl disulphide and lipoamide to the corresponding thiols, with concomitant oxidation of o-methylbenzaldehyde to methyl o-methylbenzoate.

Alane - A chemoselective way to reduce phosphine oxides

Bootle-Wilbraham, Andrew,Head, Steve,Longstaff, James,Wyatt, Paul

, p. 5267 - 5270 (1999)

Phosphine oxides may be chemoselectively reduced to phosphines in excellent yield in the presence of several other functional groups using alane. An aqueous workup is not required.

Synthesis of phenyl arylsulfonyl-alkyl-dithiocarbamates and their hydrolytic reactivity in hydroxide and hydroperoxide media

Norberto, Fatima,Araujo, M. Eduarda M.,Santos, Lidia,Jaime, Marta S. P.,Mateus, Pedro M. V.,Herves, Pablo

, p. 4710 - 4714 (2005)

Eight previously unreported phenyl arylsulfonyl-alkyl-dithiocarbamates were synthesized by treatment of arylsulfonamides with phenyl chlorodithioformate in an adaptation of a general amine acylation method. A kinetic investigation of their alkaline hydrolysis was performed and the experimental data are discussed. Wiley-VCH Verlag GmbH & Co. KGaA, 2005.

SYNTHESIS OF 3-METHYL-2-PHENYLTHIOFURAN AND 1-FORMYL-3-METHYL-2,2-DI(PHENYLTHIO)CYCLOPROPANE

Kulikovich, O. G.,Tishchenko, I. G.,Roslik, N. A.

, p. 112 (1984)

-

-

Palmer,Lossing

, p. 4661 (1962)

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Rates and Equilibria of the Michael-Type Addition of Benzenethiol to 2-Cyclopenten-1-ones

Van Castelli, Valeria Axel,Bernardi, Fernando,Cort, Antonella Dalla,Mandolini, Luigi,Rossi, Ivan,Schiaffino, Luca

, p. 8122 - 8126 (1999)

The triethylamine-catalyzed addition reactions of benzenethiol to 2-cyclopenten-1-one and its 2-and 3-methyl derivatives have been found to be appreciably reversible in chloroform solution. Rates and equilibria have been carefully measured at 25°C in order to assess the negative influence on addition exerted by methyl groups substituted on the carbon-carbon double bond. 2-Methyl-2-cyclopenten-1-one has been found to react with benzenethiol under kinetic control to give the cis adduct as the sole detectable product in a highly stereoselective anti addition process. However, on prolonged reaction times the system slowly evolved toward a new state of equilibrium in which the more stable trans adduct, derived from a syn addition mode, was the predominant isomer.

Cation-Anion Combination Reactions. 23. Solvent Effects on Rates and Equilibria of Reactions

Ritchie, Calvin D.

, p. 3573 - 3578 (1983)

Rate and equilibria constants for the reactions of 3,6-bis(dimethylamino)xanthylium cation with several amines and thiolates in dimethyl sulfoxide solution have been measured.Assumptions used in previous work to estimate equilibrium constants in dimethyl sulfoxide solution are found to be incorrect.Conclusions reached from those assumptions are not supported by the present data, and there are no examples in the present or past work where solvent effects on rates are appreciably greater than those on the corresponding equilibria for simple bond-forming reactions.Equilibrium constants have also been determined for the reactions of thiophenoxide and trifluoroethoxide ions with (p-(dimethylamino)phenyl)tropylium ion in water.The kinetic reactivities of trifluoroethoxide relative to hydroxide ion and of thiophenoxide relative to alkanethiolates are much greater than the corresponding equilibrium reactivities.In addition, an example of a slow, rate-determining, proton transfer in the reaction of morpholine with 3,6-bis(dimethylamino)xanthylium cation in dimethyl sulfoxide has been found.

Efficient Cu-catalyzed one-pot odorless synthesis of sulfides from triphenyltin chloride, aryl halides and S8 in PEG

Rostami, Abed,Rostami, Amin,Iranpoor, Nasser,Zolfigol, Mohammad Ali

, p. 192 - 195 (2016)

A novel method for the Cu(OAc)2 catalyzed synthesis of unsymmetrical sulfides from triphenyltin chloride and aryl halides using S8 as the sulfur source in PEG200 at 60-80°C is reported. Triphenyltin chloride is capable of delivering all of its phenyl groups to the product. Also, the copper catalyzed synthesis of symmetrical diaryl sulfides from aryl halides using S8 is described.

Structure-Reactivity Correlations in the Aminolysis of Phenyl and p-Nitrophenyl Thiolacetates

Castro, Enrique A.,Ureta, Carmen

, p. 2153 - 2159 (1989)

Second-order rate constants (kN) for the nucleophilic reactions of piperidine, morpholine, piperazine, and N-substituted piperazines with the title substrates are reported in water, at 25 deg C, ionic strength 0.2 M (maintained with KCl).The Broensted-type plot obtained for the aminolysis of phenyl thiolacetate is linear while that for the p-nitrophenyl derivative (NPTA) is curved, with the center of curvature at pKa=10.5 (pKa0).According to these results the most likely mechanism involves a zwitterionic tetrahedral intermediate (T+/-), for which decomposition to products is the rate-limiting step for all the reactions, except that of NPTA with piperidine.For this reaction the formation of T+/- is rate determining.A semiempirical equation based on the above hypothesis accounts for the Broensted-type curve obtained in the aminolysis of NPTA.Estimation of the microscopic rate constants involved, in a possible more general reaction scheme and evaluation of the pKa's of T+/- indicate that expulsion of the leaving group of the substrate from T+/- is faster than deprotonation of T+/- by a base, precluding therefore the formation of an anionic tetrahedral intermediate.The fact that pKa0=10.5 for the NPTA reactions means that an (hypothetical) amine of pKa=10.5 leaves T+/- as readily as p-nitrothiophenoxide ion (pKa=4.6).From these and other data it is calculated that the nucleofugality from T+/- of an amine of pKa=4.6 is ca. 3*104 times larger than that of p-nitrothiophenoxide ion.The estimated pKa0 values for the aminolysis of (hipothetical) aryl acetates with leaving groups of pKa=4.6 and 6.5 (the same pKa as thiophenol) are pKa0=8.0 and 9.0, respectively, which gives nucleofugality ratios (a given amine/aryl oxide ion) from the oxy T+/- smaller than those from the corresponding sulfur T+/-.It is claimed that expulsion of ArS- from T+/- is only slightly slower than that of an isobasic ArO- from the oxy T+/-.Therefore, the above results indicate that the "push" provided by ArS in T+/- to expel a given amine is much stronger than that exerted by an isobasic ArO in the oxy T+/-.Activation parameters are reported for the reactions of the title substrates with piperidine, piperazine, and N-formylpiperazine.

Plasmon-induced decarboxylation of mercaptobenzoic acid on nanoparticle film monitored by surface-enhanced Raman spectroscopy

Zong, Yi,Guo, Qinghua,Xu, Minmin,Yuan, Yaxian,Gu, Renao,Yao, Jianlin

, p. 31810 - 31816 (2014)

Surface plasmon plays an important role in surface catalysis reactions, and thus the tuning of plasmon on metal nanostructures and the extension of plasmon induced surface catalysis reactions have become important issues. Au nanoparticle monolayer film was fabricated by the assembling of Au nanoparticles at the liquid-air interface with numerous hot spots for strong surface plasmon coupling. A facile approach was developed to achieve the decarboxylation reaction driven by appropriate surface plasmon on the Au nanoparticle monolayer film surface, and surface enhanced Raman spectroscopy (SERS) has been developed as a sensitive tool for the in situ monitoring of the plasmon induced surface reaction. The effects of the power and wavelength of the laser and solution pH on the decarboxylation reaction were investigated. With laser illumination, para-mercaptobenzoic acid (PMBA) was transformed to thiophenol (TP), and the decarboxylation was enhanced on increasing the laser power and illumination time. The results revealed that the carboxylate groups of the adsorbed PMBA molecules were removed to produce TP, which were still adsorbed onto Au surfaces. The solution pH values exhibited a significant influence on the decarboxylation reaction. In air and neutral solution, decarboxylation proceeded at a slow rate to transform PMBA to TP, while it was absent in acidic solution. The deprotonated carboxylate group accelerated the decarboxylation for producing TP with a fast rate in alkaline solution. As a comparison, a similar plasmon driven decarboxylation reaction was observed on a Ag nanoparticle monolayer film surface. These results suggested that the transformation from PMBA to TP molecules on an Au nanoparticle film surface under laser illumination was associated with a surface-catalyzed reaction driven by local surface plasmon.

Dual Pathways in the Solvolyses of Phenyl Chlorothioformate

Kevill, Dennis N.,Bond, Michael W.,D'Souza, Malcolm J.

, p. 7869 - 7871 (1997)

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Transition-Metal-Free Approach for the Synthesis of 4-Aryl-quinolines from Alkynes and Anilines

Phanindrudu, Mandalaparthi,Wakade, Sandip Balasaheb,Tiwari, Dipak Kumar,Likhar, Pravin R.,Tiwari, Dharmendra Kumar

, p. 9137 - 9143 (2018)

An efficient and transition-metal-free approach for the synthesis of 4-arylquinolines from readily available anilines and alkynes in the presence of K2S2O8 and DMSO has been developed. A variety of alkynes and anilines having a diverse range of substitution patterns can undergo the one-pot cascade process successfully. Effectively, this method uses DMSO as one carbon source, thus providing a highly atom-economical and environmentally benign approach for the synthesis of 4-arylquinolines.

-

Kharasch,Khodair

, p. 98 (1967)

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Ligand-free copper-catalyzed synthesis of diaryl thioethers from aryl halides and thioacetamide

Tao, Chuanzhou,Lv, Aifeng,Zhao, Nan,Yang, Shuai,Liu, Xiaolang,Zhou, Jian,Liu, Weiwei,Zhao, Jing

, p. 134 - 138 (2011)

Diaryl thioethers can be prepared via a copper-catalyzed cross-coupling between aryl halides and thioacetamide using Cs2CO3 as a base and DMSO-H2O as a solvent at 120 °C. Georg Thieme Verlag Stuttgart - New York.

Development of selective colorimetric probes for hydrogen sulfide based on nucleophilic aromatic substitution

Montoya, Leticia A.,Pearce, Taylor F.,Hansen, Ryan J.,Zakharov, Lev N.,Pluth, Michael D.

, p. 6550 - 6557 (2013)

Hydrogen sulfide is an important biological signaling molecule and an important environmental target for detection. A major challenge in developing H2S detection methods is separating the often similar reactivity of thiols and other nucleophiles from H2S. To address this need, the nucleophilic aromatic substitution (SNAr) reaction of H2S with electron-poor aromatic electrophiles was developed as a strategy to separate H2S and thiol reactivity. Treatment of aqueous solutions of nitrobenzofurazan (7-nitro-1,2,3-benzoxadiazole, NBD) thioethers with H 2S resulted in thiol extrusion and formation of nitrobenzofurazan thiol (λmax = 534 nm). This reactivity allows for unwanted thioether products to be converted to the desired nitrobenzofurazan thiol upon reaction with H2S. The scope of the reaction was investigated using a Hammett linear free energy relationship study, and the determined ρ = +0.34 is consistent with the proposed SN2Ar reaction mechanism. The efficacy of the developed probes was demonstrated in buffer and in serum with associated submicromolar detection limits as low as 190 nM (buffer) and 380 nM (serum). Furthermore, the sigmoidal response of nitrobenzofurazan electrophiles with H2S can be fit to accurately quantify H2S. The developed detection strategy offers a manifold for H2S detection that we foresee being applied in various future applications.

A new procedure for thioester deprotection using thioglycolic acid in both homogeneous and heterogeneous phase

Mahler, Graciela,Saiz, Cecilia,Villamil, Valentina

, (2021/07/20)

Classic acetyl thioester protection/deprotection methodologies are widely used in organic synthesis, but deprotection step usually requires harsh conditions not suitable for labile substrates. In this work, a new method for thioester deprotection using a thiotransesterification approach is described. Firstly, thioglycolic acid (TGA) was identified as a good deprotecting reagent in solution. In order to develop a thiol polymer-supported reagent, TGA was anchored to a PEG-based resin through an amide bond (TG-NCO-SH). Both homogeneous and heterogeneous approaches were conveniently carried out at room temperature, in aqueous buffer at pH 8. The mild conditions were suitable for alkyl and phenyl thioesters. Moreover labile thioesters containing thiazolidine and oxazolidine scaffolds, bearing amine, ester and acetal functionalities were also deprotected. The polymer-supported TGA gave better deprotection yields compared to TGA in solution, yields ranging from 61 to 90%. The feasibility of the recovery and reuse of TG-NCO-SH reagent was explored, showing it can be reused at least five times without lossing the activity.

The benzyl can be selectively removed by visible light or near visible light. Method for protecting allyl and propargyl group

-

Paragraph 0030, (2021/10/16)

The invention provides a method for selectively removing benzyl, allyl and propargyl protecting groups by visible light or near visible light, namely a substrate containing benzyl, allyl or propargyl protecting groups. The method has the advantages of simple operation, safe and clean visible light or near visible light as excitation conditions, cheap and easily available reagents, high reaction yield, high reaction chemistry and regional selectivity, and is suitable for selective removal of benzyl, allyl and propargyl protecting groups in various substrates.

Transformation of arylboronic acids with sodium thiosulfate into organodisulfides catalyzed by a recyclable polyoxometalate-based Cr(iii) catalyst

Chang, Yalin,Li, Huiyi,Tao, Chaofu,Wang, Aiping,Wei, Yongge,Xie, Ya,Yu, Han,Yu, Shunming

supporting information, p. 6059 - 6064 (2021/08/23)

Organo disulfides represent an abundant class of compounds in chemical biology, pharmaceutical fields, and industry. They are traditionally synthesized by the oxidation of mercaptan in the presence of an organic ligand supported metal catalyst or toxic oxidants under harsh conditions. Here, we disclose a highly-efficient pathway in which disulfide is synthesized by organic boric acid and Na2S2O3 using the catalyst (NH4)3[CrMo6O18(OH)6], demonstrating a high activity and excellent selectivity. Various boric acid derivatives have been successfully transformed into the corresponding disulfides. Mechanistic insights have been furnished based on the observation of intermediate and control experiments.

High-performance sono/nano-catalytic system: Fe3O4?Pd/CaCO3-DTT core/shell nanostructures, a suitable alternative for traditional reducing agents for antibodies

Taheri-Ledari, Reza,Maleki, Ali,Zolfaghari, Ehsan,Radmanesh, Maral,Rabbani, Hodjattallah,Salimi, Ali,Fazel, Ramin

, (2019/11/02)

Herein, a novel heterogeneous nanoscale reducing agent for antibody cleavage, made of iron oxide nanoparticles, silica network, palladium on calcium carbonate (10%), and dithiothreitol (Fe3O4?Pd/CaCO3-DTT), is presented as a substantial alternative for traditional homogeneous analogues. Conventionally, antibody fragmentation is accomplished using reducing agents and proteases that digest or cleave certain portions of the immunoglobulin protein structure to provide active thiol sites for drug tagging aims. Then, dialysis process is needed to separate excess chemical structures and purify the reduced antibody. In this work, we have made an effort to design a suitable heterogeneous tool for protein cleavage and skip the dialysis process for purification of the reduced antibody. In this regard, firstly, various preparation methods including microwave irradiation, reflux and ultrasonication have been precisely compared, and it has been proven that the best result is obtained through 10 min ultrasound (US) irradiation using an US bath with 50 KHz frequency and 200 W L?1 power density. Then, all the necessary structural analyses have been done and thoroughly interpreted for the final product. Afterward, the catalytic performance of Fe3O4?Pd/CaCO3-DTT nanoscale system in the presence of US waves (50 KHz, 200 W) has been monitored using some disulphide derivatives. The NPs could be conveniently separated from the mixture through their substantial paramagnetic property. Thus, dialysis process in which various types of membranes are used is practically jumped after the reduction process. In this work, this is clearly demonstrated that there is a constructive synergistic effect between US waves and prepared Fe3O4?Pd/CaCO3-DTT nanoscale reducing agent. Ultimately, trastuzumab (anti HER-2) antibody has been used to test the performance of the prepared Fe3O4?Pd/CaCO3-DTT NPs in a real protein reduction reaction.

A Robust Pd-Catalyzed C-S Cross-Coupling Process Enabled by Ball-Milling

Browne, Duncan L.,Jones, Andrew C.,Nicholson, William I.,Smallman, Harry R.

supporting information, p. 7433 - 7438 (2020/10/09)

An operationally simple mechanochemical C-S coupling of aryl halides with thiols has been developed. The reaction process operates under benchtop conditions without the requirement for a (dry) solvent, an inert atmosphere, or catalyst preactivation. The reaction is finished within 3 h. The reaction is demonstrated across a broad range of substrates; the inclusion of zinc metal has been found to be critical in some instances, especially for coupling of alkyl thiols.

Process route upstream and downstream products

Process route

hydrogenchloride
7647-01-0,15364-23-5

hydrogenchloride

(phenylsulfanyl)(phenyl)diazene
42401-63-8

(phenylsulfanyl)(phenyl)diazene

benzene diazonium chloride
100-34-5

benzene diazonium chloride

thiophenol
108-98-5

thiophenol

Conditions
Conditions Yield
Benzyl phenyl sulfide
831-91-4

Benzyl phenyl sulfide

chlorobenzene
108-90-7

chlorobenzene

benzyl bromide
100-39-0

benzyl bromide

thiophenol
108-98-5

thiophenol

Conditions
Conditions Yield
anschliessendes Behandeln mit Wasser;
<i>S</i>-(4-bromo-phenyl)-cysteine
68724-10-7

S-(4-bromo-phenyl)-cysteine

ammonia
7664-41-7

ammonia

hydrogen bromide
10035-10-6,12258-64-9

hydrogen bromide

thiophenol
108-98-5

thiophenol

Conditions
Conditions Yield
optically active S-<4-bromo-phenyl>-cysteine;
phenyl benzenesulfonyl-methyl-dithiocarbamate

phenyl benzenesulfonyl-methyl-dithiocarbamate

methyl(phenylsulfonyl)amide
5183-78-8

methyl(phenylsulfonyl)amide

thiophenol
108-98-5

thiophenol

Conditions
Conditions Yield
With potassium chloride; In 1,4-dioxane; water; at 25 ℃; Kinetics;
benzenesulfinyl-phenyl-acetic acid
876494-48-3

benzenesulfinyl-phenyl-acetic acid

thiophenol
108-98-5

thiophenol

Benzoylformic acid
611-73-4

Benzoylformic acid

diphenyldisulfane
882-33-7

diphenyldisulfane

Conditions
Conditions Yield
bei der thermischen Zersetzung;
Benzyl phenyl sulfide
831-91-4

Benzyl phenyl sulfide

S-Phenyl benzenethiosulfonate
1212-08-4

S-Phenyl benzenethiosulfonate

Benzyl phenyl sulfone
3112-88-7

Benzyl phenyl sulfone

thiophenol
108-98-5

thiophenol

1,1'-(1,2-ethanediyl)bisbenzene
103-29-7

1,1'-(1,2-ethanediyl)bisbenzene

diphenyldisulfane
882-33-7

diphenyldisulfane

benzyl alcohol
100-51-6,185532-71-2

benzyl alcohol

Conditions
Conditions Yield
With aluminium(III) triflate; dichloro(4,11-dimethyl-1,4,8,11-tetraazabicyclo[6.6.2]hexadecane)manganese(II); iodosylbenzene; In acetone; at 24.84 ℃; Reagent/catalyst;
19.9%
Conditions
Conditions Yield
With sodium; In various solvent(s); at 254 ℃; for 6h; Product distribution; var. temp. and time;
95.0 % Chromat.
11.5 % Chromat.
poly[(ethylene sulfide)0.5-ran-(styrene sulfide)0.5], polycondensation product; monomer(s): α,β-dibromostyrene; 1,2-ethylene dibromide

poly[(ethylene sulfide)0.5-ran-(styrene sulfide)0.5], polycondensation product; monomer(s): α,β-dibromostyrene; 1,2-ethylene dibromide

carbon disulfide
75-15-0,12122-00-8

carbon disulfide

thiophenol
108-98-5

thiophenol

Benzo[b]thiophene
95-15-8,11095-43-5

Benzo[b]thiophene

Conditions
Conditions Yield
at 700 ℃; Product distribution;
4-Methoxybenzenethiol
696-63-9

4-Methoxybenzenethiol

chlorobenzene
108-90-7

chlorobenzene

diphenyl sulfide
139-66-2

diphenyl sulfide

1-methoxy-4-(phenylsulfanyl)benzene
5633-57-8

1-methoxy-4-(phenylsulfanyl)benzene

bis(4-methoxyphenyl)sulfide
3393-77-9

bis(4-methoxyphenyl)sulfide

thiophenol
108-98-5

thiophenol

Conditions
Conditions Yield
at 520 ℃; for 0.00694444h; Further Variations:; Temperatures; time; Kinetics; Product distribution;
dibenzothiophene
132-65-0

dibenzothiophene

3-phenyldibenzo[b,d]thiophene
98251-30-0

3-phenyldibenzo[b,d]thiophene

2-dibenzothiophenethiol
68560-31-6

2-dibenzothiophenethiol

benzene-1,4-dithiol
624-39-5

benzene-1,4-dithiol

diphenyl sulfide
139-66-2

diphenyl sulfide

1,4-bis(phenylthio)benzene
3459-94-7

1,4-bis(phenylthio)benzene

2-(phenylthio)-dibenzothiophene

2-(phenylthio)-dibenzothiophene

4-phenylmercaptothiophenol
52872-99-8

4-phenylmercaptothiophenol

[1,1'-biphenyl]-4-yl(phenyl)sulfane
59090-57-2

[1,1'-biphenyl]-4-yl(phenyl)sulfane

thiophenol
108-98-5

thiophenol

Conditions
Conditions Yield
at 650 ℃; Inert atmosphere; Pyrolysis;

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