19172-47-5

Usage

description

Lawesson's reagent, also known as Lloyd's reagent, is a commonly used chemical reagent in the preparation of organic sulfur compounds. At room temperature under normal pressure, it appears as the solid yellow powder with a strong smell of rotten. In 1956, it was first successfully produced by the reaction between arene and tetraphosphorus decasulfide. The Swedish chemist Sven-Olov Lawesson has carefully studied its reaction with organic compounds, so that its application has been greatly promoted, so the name also derived. The molecule of the Lawesson's reagent contains the four-membered ring structure alternately composed of sulfur and phosphorus. Upon being heated, it undergoes depolymerization, generating two molecules of unstable ylide (R-PS2), which are the major reactive intermediates. Upon application of the Lawesson’s reagents with two different substitution groups for reaction, it has been observed of molecules with substituent group exchanged with each other in the 31 NMR spectrum of the product, confirming the existence of the intermediates, R-PS2. Lawesson's reagent is an oxygen-sulfur exchange reagent with the most common application being for the preparation of thioamides and converting carbonyl compounds into sulfur carbonyl compounds. The reacted substrates can include ketone, ester, lactone, amide, lactam, and quinone. The electron-rich carbonyl groups are easier to react. Upon reaction with α, β-unsaturated aldehydes and ketones, the double bond is not affected.

reactions

1, aliphatic, aromatic and heterocyclic aromatic amide can have reaction with Lawson well. Tetra-sulfide is also commonly used sulfide reagents, but its usage can sometimes result in amide decomposition into nitrile and hydrogen sulfide, so that the reaction yield is reduced. 2. A mixture of silver perchlorate and Lawson's reagent can be used as an oxygen-reactive Lewis acid to catalyze the Diels-Alder reaction of dienes with α, β-unsaturated aldehydes. 3, 4-dione is cyclized to thiophene upon reaction with a Lawesson's reagent. It is also possible to react with tetrasulfide pentasulfide, but the reaction requires a higher temperature. 4, Lawesson's reagent can react with sulfoxide to generate thio products, and then generate sulfur ether through desulfurization. Therefore, it can be used as the reducing agent of sulfoxide. 5, the yield of the reaction between the Lawesson's reagent and the amide with the adjacent position of the benzene ring connecting with hydroxyl or amino group is not high, because of generating the following by-products. The reaction can be used for the preparation of thio-monoalkylphosphonate compounds.

similar products

Many compounds similar to Lawesson's reagent compounds have been prepared. They are easier to use than the Lawesson's reagent with the reaction conditions being mild and the yield being relatively high. When the methoxyphenyl group is substituted with an alkyl group such as methyl, ethyl, isopropyl or butyl, the generated reagent is called Davy reagent (DR). When the substituent group is phenylthio group, the generated reagent is referred to Japanese reagent (JR). When the substituent group is p-phenoxyphenyl group, it is referred to as the Belleau reagent (BR), All of them can be prepared from the reaction between the corresponding mercaptans and tetrasulfide pentasulfide.

Uses

Different sources of media describe the Uses of 19172-47-5 differently. You can refer to the following data:
1. Vulcanizing agents, which have recently been used to generate tropothione in situ at room temperature and capture the sulfur hybrid reagents with dienophiles.
2. Thiation reagent.
3. Lawesson's reagent is a thiation agent used to convert carbonyl compounds into thiocarbonyls. It is also used to thionate enones, esters, lactones, amides, lactams and quinones. Further, it is used to prepare thiols from alcohols. It is associated with silver perchlorate and utilized as and oxophilic Lewis acid catalyst for Diels-Alder reaction of dienes with alfa, beta-unsaturated aldehydes.

Chemical Properties

light yellow to beige powder

General Description

Lawesson′s reagent is generally used as a thiation agent in organic synthesis for the conversion of oxygen functionalities into their thio analogs. It facilitates the conversion of the carbonyl group to thiocarbonyl group as well as carbon-oxygen single bond into a carbon-sulfur single bond.

Upstream product

• 100-66-3 methoxybenzene 
• 143782-33-6 4-(4,5-dihydro-4,4-dimethyl-2-methylthio-5-oxo-1H-imidazol-1-yl) 2-trifluoromethyl-benzonitrile 
• 108-95-2 phenol 
• 15857-57-5 tetraphosphorus decasulfide 

Downstream Products

• 21778-19-8 (4-methoxyphenyl)phosphonic acid 
• 37632-19-2 4-methoxyphenylphosphonothioic dichloride 
• 21990-58-9 tetra-N-ethyl-2-(4-methoxy-phenyl)-2-thioxo-2H-2λ⁵-[1,3,5,2]thiadiazaphosphinine-4,6-diamine 
• 74554-59-9 2-(4-methoxy-phenyl)-6-phenyl-2-thioxo-2,3-dihydro-2λ⁵-[1,3,2]oxazaphosphinine-4-thione 
• 74554-60-2 6-benzyl-2-(4-methoxy-phenyl)-5-phenyl-2-thioxo-2,3-dihydro-2λ⁵-[1,3,2]oxazaphosphinine-4-thione 
• 17847-89-1 p-Methoxy-phenyl-aethyl-dithiophosphinsaeure 
• 17847-92-6 (4-Methoxyphenyl)phenyldithiophosphinsaeure 
• 137171-51-8 2,4,6-tris(4-methoxyphenyl)-2,4,6-trisulfanylene-1,3,5,2,4,6-trioxatriphosphinane 
• 22074-95-9 2-(4-methoxy-phenyl)-4,6-di-piperidin-1-yl-2H-[1,3,5,2]thiadiazaphosphinine 2-sulfide 
• 37934-56-8 tetra-N-ethyl-4-(4-methoxy-phenyl)-3,5-dimethyl-4-thioxo-4H-4λ⁵-[1,4]thiaphosphinine-2,6-diamine 
• 74554-61-3 2-(4-methoxy-phenyl)-2-thioxo-2,3,5,6,7,8-hexahydro-2λ⁵-benzo[e][1,3,2]oxazaphosphinine-4-thione 
• 104236-63-7 2-(4-Methoxyphenyl)-1,3,2-dithiaphosphorinane 2-sulfide 
• 93031-68-6 4-Ethyl-2-(4-methoxy-phenyl)-[1,3,2]dithiaphospholane 2-sulfide 
• 78906-58-8 piperidinium N,N'-pentamethylene-4-methoxyphenylphosphonamidodithioate 

Relevant academic research and scientific papers

Synergistically enhanced performance of transition-metal doped Ni2P for supercapacitance and overall water splitting

Cost-effective and readily available catalysts applicable for electrochemical conversion technologies are highly desired. Herein, we report the synthesis of dithiophosphonate complexes of the type [Ni{S2P(OH)(4-CH3OC6H4)}2] (1), [Co{S2P(OC4H9)(4-CH3OC6H4)}3] (2) and [Fe{S2P(OH)(4-CH3OC6H4)}3] (3) and employed them to prepare Ni2P, Co-Ni2P and Fe-Ni2P nanoparticles. Ni2P was formed by a facile hot injection method by decomposing complex1in tri-octylphosphine oxide/tri-n-octylphosphine at 300 °C. The prepared Ni2P was doped with Co and Fe employing complexes2and3, respectively, under similar experimental conditions. Doping Ni2P with Co and Fe demonstrated synergistic improvement of Ni2P performance as an electrocatalyst in supercapcitance, hydrogen evololution and oxygen evolution reactions in alkaline medium. Cobalt doping improved the Ni2P charge storage capacity with a supercapacitance of 864 F g?1at 1 A g?1current density. Fe doped Ni2P recorded the lowest overpotential of 259 mV to achieve a current density of 10 mA cm?2and a Tafel slope of 80 mV dec?1for OER, better than the undoped Ni2P and the benchmark IrO2. Likewise, Fe-doped Ni2P electrode required the lowest overpotential of 68 mV with a Tafel slope of 110 mV dec?1to attain the same current density for HER. All catalysts showed excellent stability in supercapacitance and overall water splitting reactions, indicating their practical use in energy conversion technologies.

Sulfur-rich nickel(II) complex: Synthesis, characterization, and X-ray crystal structure

A sulfur-rich nickel complex has been synthesized by the reaction between 2,4-bis(4-methoxyphenyl)- 1,3,2,4-dithiadiphosphetane-2,4-disulfide (Lawesson’s reagent) and Ni(NO3)2·6H2O in 2-propanol. The complex has been characterized by elemental analysis, IR,1H NMR,13C NMR, and31P NMR spectroscopies and molar conductivity. Also, the crystal structure of the complex has been investigated by X-ray diffraction, which illustrates a slightly distorted square planar environment around Ni(II) ion in solid. Furthermore, the crystal structure of the complex shows 3D network through intermolecular C-H…Ni, CH O, and C-H S hydrogen bonds and C–H π interaction.

Syntheses, characterization of and studies on the electrochemical behaviour of ferrocenyl dithiophosphonates and 4-methoxyphenyl dithiophosphonates

Some 1,3-dithiadiphosphetane 2,4-disulfides (X2P2S4, X: Fc, FcLR; X: CH3O?C6H4?, LR) were allowed to react with alcohols to obtain dithiophosphonic acids (X(OR)PS2H). These were converted to the corresponding ammonium salts. The salts were of the structures [Fc(OR)PS2]?[NH4]+, R: 3-methyl-1-butyl- for I; 1-phenyl-1-propyl- for II; 3-pentyl- for III; 3-phenyl-1-propyl- for IV and [CH3O?C6H4(OR)PS2]?[NH4]+, R: 3-methyl-1-butyl- for V and 1-phenyl-1-propyl- for VI. To the best of our knowledge, all the compounds except V were prepared for the first time. The compounds synthesized were characterized by elemental analysis, NMR (1H,13C,31P), MS, FTIR, and Raman spectroscopies. Electrochemical behaviors of I–VI at disposable pencil graphite electrode (PGE) were investigated by using cyclic voltammetry (CV) and square-wave voltammetry (SWV). Adsorption and diffusion patterns of all the compounds on the PGE were also studied. Two electroactive groups were identified in the compounds I–IV and only one in V and VI. The ferrocenyl groups of I-IV were oxidized at around 0.4?V. The same compounds display a second, more intense CV band at 0.8?V. The corresponding band for the compounds V–VI appears at around 0.6?V with a much weaker intensity. It is suggested that the ferrocenyl group introduced into the structures stabilizes the radical species formed as the product of the oxidation of the dithiophosphonato group.

Flexible Molecular Precursors for Selective Decomposition to Nickel Sulfide or Nickel Phosphide for Water Splitting and Supercapacitance

Herein, the synthesis of three nickel(II) dithiophosphonate complexes of the type [Ni{S2P(OR)(4-C6H4OMe)}2] [R=H (1), C3H7 (2)] and [Ni{S2P(OR)(4-C6H4OEt}2] [R=(C6H5)2CH (3)] is described; their structures were confirmed by single-crystal X-ray studies. These complexes were subjected to surfactant/solvent reactions at 300 °C for one hour as flexible molecular precursors to prepare either nickel sulfide or nickel phosphide particles. The decomposition of complex 2 in tri-octylphosphine oxide/1-octadecene (TOPO/ODE), TOPO/tri-n-octylphosphine (TOP), hexadecylamine (HDA)/TOP, and HDA/ODE yielded hexagonal NiS, Ni2P, Ni5P4, and rhombohedral NiS, respectively. Similarly, the decomposition of complex 1 in TOPO/TOP and HDA/TOP yielded hexagonal Ni2P and Ni5P4, respectively, and that of complex 3 in similar solvents led to hexagonal Ni5P4, with TOP as the likely phosphorus provider. Hexagonal NiS was prepared from the solvent-less decomposition of complexes 1 and 2 at 400 °C. NiS (rhom) had the best specific supercapacitance of 2304 F g?1 at a scan rate of 2 mV s?1 followed by 1672 F g?1 of Ni2P (hex). Similarly, NiS (rhom) and Ni2P (hex) showed the highest power and energy densities of 7.4 kW kg?1 and 54.16 W kg?1 as well as 6.3 kW kg?1 and 44.7 W kg?1, respectively. Ni5P4 (hex) had the lowest recorded overpotential of 350 mV at a current density of 50 mA cm?2 among the samples tested for the oxygen evolution reaction (OER). NiS (hex) and Ni5P4 (hex) had the lowest overpotentials of 231 and 235 mV to achieve a current density of 50 mA cm?2, respectively, in hydrogen evolution reaction (HER) examinations.

Preparation method and application of multifunctional ultraviolet absorbent

The invention relates to a preparation method and application of a multifunctional ultraviolet absorbent for terylene. The general structural formula of the absorbent is as follows: formula, wherein Y is a quaternary ammonium salt group. According to the preparation method and application of the multifunctional ultraviolet absorbent for terylene disclosed by the invention, the dyeing mode of the ultraviolet absorbent to terylene is similar to disperse dyes, and fabrics can be subjected to anti-ultraviolet finishing by using a high-temperature and high-pressure exhausting method and can also be dyed with the disperse dyes in the same bath; the finished fabrics not only have good anti-ultraviolet properties, but also have the effects of killing or inhibiting Gram-positive bacteria and Gram-negative bacteria represented by staphylococcus aureus and Escherichia coli; and meanwhile, the fabrics have good anti-static function.

An Aluminum(III)-Catalyzed Thioamide-Aldehyde-Styrene Condensation: Direct Synthesis of Allylic Thioamide Derivatives

An aluminum(III) triflate catalyzed three-component synthesis of allylic thioamide derivatives by condensation of a thioamide, paraformaldehyde and a styrene is reported.

A highly selective and naked-eye sensor for Hg2+ based on quinazoline-4(3H)-thione

A highly selective colorimetric and fluorescent sensor for Hg2+, TPS (TPS = 2-(4-(diphenyl-amino)phenyl)quinazoline-4(3H)-thione), based on a 2-substituted quinazoline-4(3H)-thione derivative, was designed and characterized in this paper. TPS displays relatively strong fluorescence centered at about 468 nm. When mixing with Hg2+, TPS interacts with Hg2+ in a 2:1(TPS-Hg2+) stoichiometry via a coordination bond interaction between the sulfur atom and Hg2+ with an association constant of 4.17 × 108 M-2 (R2 = 0.96). Upon addition of Hg2+, TPS showed a remarkable decrease in fluorescence spectra (468 nm) with a clear color change from yellow to red, so TPS could serve as a naked-eye sensor for Hg2+. The sensor allow determination of Hg2+ in the working range 2.0 μM-12.0 μM with a detection limit of 1.5 μM. Upon addition of KI to the solution of TPS-Hg2+ species, the spectra can be restored to the original spectrum in both absorption and fluorescence and indicates that this sensor could be reused. The sensor exhibited excellent reproducibility, reversibility and selectivity.

1,4-OXAZEPINES AS BACE1 AND/OR BACE2 INHIBITORS

The present invention relates to 1,4 Oxazepines of formula I having BACE1 and/or BACE2 inhibitory activity, their manufacture, pharmaceutical compositions containing them and their use as therapeutically active substances. The active compounds of the present invention are useful in the therapeutic and/or prophylactic treatment of e.g. Alzheimer's disease and type 2 diabetes.

Derivatives of 4- or 5-aminosalicylic acid

The present invention provides new derivatives of 4- or 5-aminosalicylic acid, and a pharmaceutical composition containing these derivatives of 4- or 5-aminosalicylic acid as active ingredients, useful for the treatment of intestinal diseases such as inflammatory bowel disease (IBD) and irritable bowel syndrome (IBS) and for the prevention/treatment of colon cancer. More particularly, these derivatives comprise a hydrogen sulfide releasing moiety linked via an azo, an ester, an anhydride, a thioester or an amide linkage to a molecule of 4- or 5-aminosalicylic acid. Furthermore, the present invention provides a process for preparing these compounds and their use for treating IBD and IBS and the prevention/treatment of colon cancer.

Thiophosphonate inhibitors of phosphatase enzymes and metallophosphatases

Compounds of the general formula wherein R is selected from the group consisting essentially of hydrogen, methyl, ethyl, phenyl, a carboxyl, or naphthyl substituted or a carbonyl substituted, alkyl of from 3 to 20 carbon atoms, a mono, bi or tri cyclic aryl or substituted aryl for the inhibition of phosphatase enzymes, including metallophosphatases; and, novel methods for synthesizing such compounds. The methods of use include the administration of an effective amount of the compound to provide effective phosphatase inhibition and therapeutic use to treat or prevent certain diseases, which utilize specific phosphatase enzymes.