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Lawesson's reagent

Base Information Edit
  • Chemical Name:Lawesson's reagent
  • CAS No.:19172-47-5
  • Deprecated CAS:114668-60-9,136390-48-2,72728-81-5,94367-93-8,136390-48-2,72728-81-5,94367-93-8
  • Molecular Formula:C14H14O2P2S4
  • Molecular Weight:404.475
  • Hs Code.:29349990
  • European Community (EC) Number:242-855-4
  • NSC Number:150550
  • UNII:A4125MQ8RX
  • DSSTox Substance ID:DTXSID4066460
  • Nikkaji Number:J208.098B,J323.927F
  • Wikipedia:Lawesson%27s_reagent,Lawesson's_reagent
  • Wikidata:Q419324
  • Mol file:19172-47-5.mol
Lawesson's reagent

Synonyms:2,4-bis(4-methoxyphenyl)-1,3,2,4-dithiadiphosphetane-2,4-disulfide;2,4BMP-DTDPDS;Lawesson's reagent;p-anisyldithiophosphonic anhydride

Suppliers and Price of Lawesson's reagent
Supply Marketing:Edit
Business phase:
The product has achieved commercial mass production*data from LookChem market partment
Manufacturers and distributors:
  • Manufacture/Brand
  • Chemicals and raw materials
  • Packaging
  • price
  • TRC
  • Lawesson’sReagent
  • 50g
  • $ 305.00
  • TCI Chemical
  • Lawesson's Reagent [Sulfurating Reagent] >95.0%(T)
  • 25g
  • $ 30.00
  • TCI Chemical
  • Lawesson's Reagent [Sulfurating Reagent] >95.0%(T)
  • 250g
  • $ 223.00
  • Sigma-Aldrich
  • Lawesson reagent 97%
  • 100g
  • $ 97.50
  • Sigma-Aldrich
  • Lawesson reagent 97%
  • 10g
  • $ 23.50
  • Sigma-Aldrich
  • Lawesson reagent 97%
  • 25g
  • $ 36.40
  • Oakwood
  • Lawesson's reagent
  • 25g
  • $ 30.00
  • Oakwood
  • Lawesson's reagent
  • 1g
  • $ 9.00
  • Oakwood
  • Lawesson's reagent
  • 10g
  • $ 20.00
  • Oakwood
  • Lawesson's reagent
  • 5g
  • $ 15.00
Total 142 raw suppliers
Chemical Property of Lawesson's reagent Edit
Chemical Property:
  • Appearance/Colour:light yellow to beige powder 
  • Melting Point:228-230 °C(lit.) 
  • Boiling Point:525.779 °C at 760 mmHg 
  • Flash Point:271.782 °C 
  • PSA:152.86000 
  • Density:1.489 g/cm3 
  • LogP:6.05480 
  • Storage Temp.:water-free area 
  • Sensitive.:Moisture Sensitive 
  • Water Solubility.:Decomposition 
  • XLogP3:6.1
  • Hydrogen Bond Donor Count:0
  • Hydrogen Bond Acceptor Count:6
  • Rotatable Bond Count:4
  • Exact Mass:403.93518837
  • Heavy Atom Count:22
  • Complexity:425
Purity/Quality:

99% *data from raw suppliers

Lawesson’sReagent *data from reagent suppliers

Safty Information:
  • Pictogram(s): HarmfulXn, IrritantXi, Flammable
  • Hazard Codes:Xn-F,Xi,Xn,F 
  • Statements: 20/21/22-15/29-37 
  • Safety Statements: 8-43-36/37-22-38-7/8 
MSDS Files:

SDS file from LookChem

Useful:
  • Chemical Classes:Other Classes -> Sulfur Compounds
  • Canonical SMILES:COC1=CC=C(C=C1)P2(=S)SP(=S)(S2)C3=CC=C(C=C3)OC
  • 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.
  • Uses Vulcanizing agents, which have recently been used to generate tropothione in situ at room temperature and capture the sulfur hybrid reagents with dienophiles. Thiation reagent. 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.
Technology Process of Lawesson's reagent

There total 6 articles about Lawesson's reagent which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:
Guidance literature:
Guidance literature:
With tetraphosphorus decasulfide; for 6h; Heating;
DOI:10.1080/10426500008082393
Guidance literature:
at 700 ℃; flash vacuum pyrolysis;
Refernces Edit

New camphor-derived sulfur chiral controllers: Synthesis of (2R-exo)-10-methylthio-2-bornanethiol and (2R-exo)-2,10-bis(methylthio)bornane

10.1016/S0957-4166(96)00463-6

The study focuses on the efficient synthesis of two camphor-derived chiral controllers, (2R-exo)-10-methylthio-2-bornanethiol (lb) and (2R-exo)-2,10-bis(methylthio)bornane (2), which have potential applications as ligands or chiral auxiliaries in asymmetric synthesis. The key starting material is (1S)-camphor-10-thiol (3), which is converted through a series of reactions involving benzoyl chloride, Lawesson's reagent, lithium aluminum hydride (LiAlH4), and diisobutylaluminum hydride (DIBAL-H) to achieve the desired chiral compounds. The study highlights the stereoselective reduction of thiones as a crucial method for introducing sulfur functionality in position 2 of the camphor-derived compounds. The synthesized compounds are characterized by various spectroscopic techniques, and their potential use in catalytic asymmetric hydroformylation and Pauson-Khand reactions is discussed.

A Ramberg-Baecklund route to the stilbenoid anti-cancer agents combretastatin A-4 and DMU-212

10.1039/b702411h

The study presents a concise synthetic route to the anti-cancer agents combretastatin A-4 and DMU-212 using the Ramberg–B?cklund reaction. Combretastatin A-4, isolated from the African tree Combretum caffrum, is a potent inhibitor of tubulin polymerization, while DMU-212 is a synthetic analogue with cancer chemoprotective activity. The synthesis of combretastatin A-4 begins with the coupling of thiol 13, prepared from 3,4,5-trimethoxybenzyl alcohol using Lawesson’s reagent, and bromide 14, using potassium hydroxide in ethanol. The resulting sulfide is oxidized with m-chloroperoxybenzoic acid to form sulfone 12. The Ramberg–B?cklund reaction, carried out under various conditions (Meyers, Chan, and Franck), converts sulfone 12 into the stilbene intermediate 15, which is then desilylated to yield combretastatin A-4. The study also explores the synthesis of other combretastatin analogues, including (E)- and (Z)-2012, using similar procedures. The Ramberg–B?cklund reaction is further applied to prepare DMU-212 from sulfone 29, derived from 4-methoxybenzyl mercaptan and bromide 17. The study highlights the efficiency and stereoselectivity of the Ramberg–B?cklund reaction in synthesizing these anti-cancer stilbenes and provides insights into the reaction's scope and limitations.

Synthesis of original trifluoromethylated 6-aryl-pyridazines fused with thiazolidine or 1,2,4-triazole

10.1055/s-2005-918433

The research aims to develop an efficient synthesis of novel 8-trifluoromethyl-7H-thiazolo[3,2-b]- and 1,2,4-triazolo[4,3-b]pyridazines, which are potentially biologically active compounds. The study builds on the known pharmacological properties of 6-aryl-1,2,4-triazolo[4,3-b]pyridazine derivatives, such as their anxiolytic and antihypertensive effects, and explores the impact of incorporating a trifluoromethyl group at a unique position on these molecules. The synthesis starts from 4-trifluoromethyl-4,5-dihydropyridazin-3-one, using a five-membered ring closure strategy involving bis(electrophilic) reagents reacting with exocyclic and endocyclic nucleophilic centers on the pyridazine nucleus. Key chemicals include Lawesson’s reagent for thionation, methyl α-bromoacetate for ring closure, and various reagents like phosphorous oxy chloride and hydrazine for further functional group transformations. The study concludes that the synthesized compounds, such as 4, 8, 9, and 10a/b, can be efficiently accessed under mild conditions and are promising candidates for further biological evaluation due to their unique structure and potential for chemical transformations.

THE SYNTHESIS OF THIENOTRIAZOLOTHIAZEPINES

10.3987/COM-90-5442

The study detail the first synthesis of thienotriazolothiazepines, a novel heteroazepine derivative with anti-PAF (platelet activating factor) activity. The researchers synthesized these compounds to explore their potential as potent and orally active PAF antagonists. The synthetic route involved several steps, including the formation of 2-aminothiophenes, protection and reduction of amino groups, Mitsunobu conditions to form sulfides, hydrolysis to carboxylic acids, cyclization to form thiazepine rings, and the construction of triazole rings using Lawesson's reagent and subsequent treatments with hydrazine monohydrate and trimethyl orthoacetate. The synthesized thienotriazolothiazepines were tested for their ability to inhibit rabbit platelet aggregation induced by PAF, and all compounds exhibited anti-PAF activity. The study concludes that the synthesized compounds are effective in inhibiting PAF-induced platelet aggregation, suggesting their potential as therapeutic agents for conditions related to platelet aggregation.

The Syntheses of Triazole, Sulfur-Containing Diazole and N-Phenylthiatriazole Biphenyltetrazoles as Potential Angiotensin II Receptor Antagonists

10.1002/jccs.199600014

The study focuses on the synthesis of novel triazole, sulfur-containing diazole, and N-phenylthiatriazole biphenyltetrazole derivatives as potential angiotensin II receptor antagonists. This research was inspired by the success of the angiotensin II receptor antagonist losartan (DuP 753) and aimed to explore alternative heterocycles that could maintain or enhance its efficacy. Chemicals such as methyl valerimidate hydrochloride, thionyl chloride, N-methylmorpholine, cesium carbonate, and Lawesson's reagent were used in the synthetic processes. Among the synthesized compounds, 5-butyl-3-[(2-trifluoromethyl)phenyl]-2,1,3,4-1H-thiatriazole-2-one biphenyltetrazole demonstrated promising in vitro activity, suggesting its potential for further pharmaceutical development?.

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