19172-47-5

Basic information

• Product Name: Lawesson's Reagent
• Synonyms: 1,3,2,4-dithiadiphosphetane,2,4-bis(4-methoxyphenyl)-,2,4-disulfide;P-METHOXYPHENYLTHIONOPHOSPHINE SULFIDE DIMER;P-METHOXYPHENYLTHIOPHOSPHINE SULFIDE, DIMER;LR;LAWESSON REAGENT;LAWESSON'S REAGENT;AURORA KA-1707;4-METHOXYPHENYLTHIOPHOSPHORIC CYCLIC DI(THIOANHYDRIDE)
• CAS NO: 19172-47-5
• Molecular Formula: C₁₄H₁₄O₂P₂S₄
• Molecular Weight: 404.47
• EINECS: 242-855-4
• Product Categories: Dithietanes;Simple 4-Membered Ring Compounds;Sulfur Compounds (for Synthesis);Synthetic Organic Chemistry;Ring Systems
• Mol File: 19172-47-5.mol
• Article Data: 23

Chemical Properties

• Melting Point: 228-230 °C(lit.)
• Boiling Point: 525.779 °C at 760 mmHg
• Flash Point: 271.782 °C
• Appearance: White to almost white/Powder
• Density: 1.489 g/cm³
• Storage Temp.: water-free area
• Water Solubility: Decomposition
• Sensitive: Moisture Sensitive
• Merck: 14,5391
• BRN: 1024888
• CAS DataBase Reference: Lawesson's Reagent(CAS DataBase Reference)
• NIST Chemistry Reference: Lawesson's Reagent(19172-47-5)
• EPA Substance Registry System: Lawesson's Reagent(19172-47-5)

Safety Data

• Hazard Codes: Xn-F,Xi,Xn,F
• Statements: 20/21/22-15/29-37
• Safety Statements: 8-43-36/37-22-38-7/8
• RIDADR: 3278
• WGK Germany: 3
• F: 13-21
• TSCA: Yes
• HazardClass: 4.3
• PackingGroup: III
• Hazardous Substances Data: 19172-47-5(Hazardous Substances Data)

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

Downstream Products

• 21778-19-8 (4-methoxyphenyl)phosphonic acid 
• 37632-19-2 4-methoxyphenylphosphonothioic dichloride 
• 22074-95-9 2-(4-methoxy-phenyl)-4,6-di-piperidin-1-yl-2H-[1,3,5,2]thiadiazaphosphinine 2-sulfide 
• 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 
• 74554-62-4 2-(4-methoxy-phenyl)-6-methyl-5-phenyl-2-thioxo-2,3-dihydro-2λ⁵-[1,3,2]oxazaphosphinine-4-thione 
• 104236-63-7 2-(4-Methoxyphenyl)-1,3,2-dithiaphosphorinane 2-sulfide 
• 78906-50-0 C₁₀H₁₆NOPS₂*C₃H₉N 
• 142707-84-4 2-(4-Methoxy-phenyl)-6-pyridin-4-yl-[1,2,4]triazolo[4,3-d][1,3,4,2]thiadiazaphosphole 2-sulfide 
• 67438-42-0 1-(4-methoxyphenyl)-3-piperidino-prop-2-enthione 
• 3354-42-5 3H-1,2-benzodithiole-3-thione 
• 137171-51-8 2,4,6-tris(4-methoxyphenyl)-2,4,6-trisulfanylene-1,3,5,2,4,6-trioxatriphosphinane 
• 93546-29-3 2-Undecyl-benzo[1,3]dithiin-4-one 
• 93546-30-6 2-Undecyl-benzo[1,3]dithiine-4-thione 
• 1056-77-5 2,3,4,5-tetraphenylfuran 

Relevant articles and documents

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.

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.

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.