Xn:Harmful;
106-45-6Relevant articles and documents
Palladium catalyzed synthesis of aryl thiols: Sodium thiosulfate as a cheap and nontoxic mercapto surrogate
Yi, Jun,Fu, Yao,Xiao, Bin,Cui, Wei-Chen,Guo, Qing-Xiang
, p. 205 - 208 (2011)
A Pd-catalyzed coupling reaction of ArBr/ArCl/ArOTf with sodium thiosulfate takes place in presence of Cs2CO3 at 80 °C. The reaction mixture is directly treated with Zn/HCl to afford aryl thiols in good to excellent yields.
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
, (2020)
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.
Non-aqueous reduction of aromatic sulfonyl chlorides to thiols using a dichlorodimethylsilane-zinc-dimethylacetamide system
Uchiro, Hiromi,Kobayashi, Susumu
, p. 3179 - 3182 (1999)
A new and efficient method for the non-aqueous reduction of sulfonyl chlorides to affored the corresponding thiols by use of a dichlorodimethylsilane-zinc-dimethylacetamide system was successfully developed. Various aromatic thiols were prepared in high yield by easy operation. Continuous reactions with the above reduction using the prepared thiol were also demonstrated.
REDUCTION OF SULFONIC ACIDS WITH PHOSPHORUS PENTASULFIDE
Oae, Shigeru,Togo, Hideo
, p. 4701 - 4704 (1982)
Arene, and alkanesulfonic acids are easily reduced to the corresponding polysulfides R-(S)n-R (n= 2.9 3.3) by treatment with phosphorus pentasulfide.In this reaction, the formation of both P-O-S and P-S-H linkages is considered to be involved in the key step of the reduction.
SYNTHESIS OF AROMATIC THIOLS FROM ARYL IODIDES AND THIOUREA BY MEANS OF NICKEL CATALYST
Takagi, Kentaro
, p. 1307 - 1308 (1985)
Nickel(0) complex, generated in situ from bis(triethylphosphine)nickel(II) chloride and sodium cyanoborohydride, catalyzed the nucleophilic displacement of aryl iodides with thiourea.S-Aryl-isothiuronium salts or aromatic thiols were obtained in good yields after simple work-up procedures.
Copper-Catalyzed Direct Synthesis of Aryl Thiols from Aryl Iodides Using Sodium Sulfide Aided by Catalytic 1,2-Ethanedithiol
Xue, Hongyu,Jing, Bing,Liu, Shasha,Chae, Junghyun,Liu, Yajun
, p. 2272 - 2276 (2017)
A copper-catalyzed direct and effective synthesis of aryl thiols from aryl iodides using readily available Na 2 S·9H 2 O and 1,2-ethanedithiol was described. A variety of aryl thiols were readily obtained in yields of 76-99%. In this protocol, Na 2 S·9H 2 O was used as ultimate sulfur source, and 1,2-ethanedithiol functioned as an indispensable catalytic reagent.
Nucleophilic Substitution Reactions of Aryl N-Phenyl Thiocarbamates with Benzylamines in Acetonitrile
Oh, Hyuck Keun,Park, Jie Eun,Sung, Dae Dong,Lee, Ikchoon
, p. 3150 - 3153 (2004)
The aminolysis reactions of aryl N-phenythiocarbamates (PhNHC(=O)SC 6H4Z; 3b) with benzylamines (XC6H 4CH2NH2) acetonitrile are studied. Rates are much faster than the corresponding reactions of aryl N-phenylcarbamates (PhNHC(=O)OC6H4Z; 3a). The rate increase from 3a to 3b is greater than that expected from substitution of thiophenoxide for phenoxide leaving group in the stepwise aminolysis reactions of esters. This large rate increase and the similar change in the aminolysis rates that are reported to occur from aryl ethyl carbonate (EtOC(=O)OC6H4Z; 2a) to aryl ethylthiocarbonate (EtOC(=O)SC6H4Z; 2b) lead us to conclude that the aminolysis of 3b proceeds by a concerted mechanism in contrast to a stepwise process for 3a. The negative ρxz values (-0.63) and violation of the reactivity-selectivity principle (RSP) support the proposed mechanism. The large βx values (1.3-1.5) obtained are considered to indicate a large degree of bond making in the transition state, which is consistent with the relatively large kinetic isotope effects (k H/kD > 1.0) observed.
Copper-catalyzed coupling of thiourea with aryl iodides: The direct synthesis of aryl thiols
Qiao, Shu,Xie, Kun,Qi, Junsheng
, p. 1441 - 1443 (2010)
A general, economical and efficient protocol for the direct copper-catalyzed coupling of thiourea with aryl iodides is developed and it will be potentially applied in large-scale industry as a preferred process.
IODINE CATALYZED REDUCTION OF ARENESULFONIC ACID TO THE ARENETHIOL WITH TRIPHENYLPHOSPHINE
Fujimori, Ken,Togo, Hideo,Oae, Shigeru
, p. 4921 - 4924 (1980)
Arenesulfonic acids, its sodium salts, and alkyl arenesulfonates were reduced readily to the corresponding arenethiols quantitatively with triphenylphosphine in the presence of iodine.
Thiol radical cations and thiyl radicals as direct products of the free electron transfer from aromatic thiols to n-butyl chloride radical cations
Hermann, Ralf,Dey, Ghasi Ram,Naumov, Sergej,Brede, Ortwin
, p. 1213 - 1220 (2000)
Radical and ionic reactions were observed in the pulse radiolysis of thiophenols (ArSH = thiophenol, o-, m- and p-thiocresol or 2-thionaphthol) in n-butyl chloride solution. The main source of aromatic thiyl radicals is the reaction of butyl radicals with the thiols, which proceeds at 1.0-5.6 x 108 dm3 mol-1 s-1. This radical generation path is completely quenched in the presence of oxygen. Under these conditions, only the electron transfer reaction between n-butyl chloride parent ions and the thiophenols remains and could be well analyzed. It takes place at a rate constant of about 1.5 x 1010 dm3 mol-1 s-1 and takes two parallel paths-common electron transfer yielding thiophenol radical cations and a more complex ionic reaction resulting directly in thiyl radicals. The latter is thought to proceed via an encounter complex geometry, ArSH···ClBu.+, in which electron transfer is directly followed by immediate deprotonation. The thiyl radicals and the thiol radical cations are characterized by their optical absorption spectra and their kinetic properties. Quantum chemical calculations underpin our mechanistic interpretation and provide information about the charge distribution and reactivity of the thiol radical cations.
