Lawesson's reagent

Base Information

• 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

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

Chemical Property of Lawesson's reagent

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): Xn, Xi, F
• 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:

Reference yield: 95.8%

→ Lawessons reagent (19172-47-5,94367-93-8)

Guidance literature:

Reference yield: 88.0%

methoxybenzene (100-66-3) → Lawessons reagent (19172-47-5,94367-93-8)

Guidance literature:

With tetraphosphorus decasulfide; for 6h; Heating;

DOI:10.1080/10426500008082393

Reference yield: 80.0%

2-(4-Methoxy-phenyl)-[1,3,2]dithiaphospholane → Lawessons reagent (19172-47-5,94367-93-8) + ethene (74-85-1)

Guidance literature:

at 700 ℃; flash vacuum pyrolysis;

upstream raw materials:

methoxybenzene

4-(4,5-dihydro-4,4-dimethyl-2-methylthio-5-oxo-1H-imidazol-1-yl) 2-trifluoromethyl-benzonitrile

phenol

tetraphosphorus decasulfide

Downstream raw materials:

1-phenyl-3-piperidino-2-propene-1-thione

1,2-dihydro-2,4-bis(p-methoxyphenyl)-2,1,3-benzophosphadiazine-2-sulphide

2-(4-methoxy-phenyl)-2-thioxo-2,3,5,6,7,8-hexahydro-2λ⁵-benzo[e][1,3,2]oxazaphosphinine-4-thione

2-(4-methoxy-phenyl)-6-phenyl-2-thioxo-2,3-dihydro-2λ⁵-[1,3,2]oxazaphosphinine-4-thione

Refernces

• 1、 Jafari, Hadi,Zarei, Seyed Amir. "Sulfur-rich nickel(II) complex: Synthesis, characterization, and X-ray crystal structure". . p. 260 - 263. Retrieved 2017.
• 2、 Ayom, Gwaza E.,Gupta, Ram K.,Ingsel, Tenzin,Khan, Malik D.,Lin, Wang,Revaprasadu, Neerish,Zamisa, Sizwe J.,van Zyl, Werner E.. "Flexible Molecular Precursors for Selective Decomposition to Nickel Sulfide or Nickel Phosphide for Water Splitting and Supercapacitance". . p. 2693 - 2704. Retrieved 2020/03/04.