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Lawesson's Reagent

Lawesson's Reagent Structure
Lawesson's Reagent structure
CAS No.
19172-47-5
Chemical Name:
Lawesson's Reagent
Synonyms
LAWESSON REAGENT;Lawesson;LR;2,4-BIS(4-METHOXYPHENYL)-2,4-DITHIOXO-1,3,2,4-DITHIADIPHOSPHETANE;2,4-BIS(4-METHOXYPHENYL)-1,3-DITHIA-2,4-DIPHOSPHETANE-2,4-DISULFIDE;Lawesson's;242-855-4;Lawesson`s reagentsulfide dimer;2,4-BIS(4-METHOXYPHENYL)-1,3,2,4-DITHIADIPHOSPHETANE-2,4-DISULFIDE;4-Methoxyphenylthiophosphoric cyclic di(thioanhydride), LR, 2,4-Bis(4-methoxyphenyl)-2,4-dithioxo-1,3,2,4-dithiadiphosphetane, 2,4-Bis-(4-methoxyphenyl)-1,3-dithia-2,4-diphosphetane 2,4-disulfide
CBNumber:
CB8128537
Molecular Formula:
C14H14O2P2S4
Molecular Weight:
404.47
MDL Number:
MFCD00005171
MOL File:
19172-47-5.mol
MSDS File:
SDS
TDS File:
TDS
Last updated:2026-05-28 03:18:20
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Lawesson's Reagent Properties

Melting point 228-230 °C(lit.)
Boiling point 525.8±60.0 °C(Predicted)
Density 1.48±0.1 g/cm3(Predicted)
storage temp. Inert atmosphere,2-8°C
solubility Chloroform (Slightly)
form Powder
color White to almost white
Water Solubility Decomposition
Sensitive Moisture Sensitive
Merck 14,5391
BRN 1024888
InChI InChI=1S/C14H14O2P2S4/c1-15-11-3-7-13(8-4-11)17(19)21-18(20,22-17)14-9-5-12(16-2)6-10-14/h3-10H,1-2H3
InChIKey CFHGBZLNZZVTAY-UHFFFAOYSA-N
SMILES S1P(=S)(C2=CC=C(OC)C=C2)SP1(=S)C1=CC=C(OC)C=C1
CAS DataBase Reference 19172-47-5(CAS DataBase Reference)
FDA UNII A4125MQ8RX
EPA Substance Registry System 1,3,2,4-Dithiadiphosphetane, 2,4-bis(4-methoxyphenyl)-, 2,4-disulfide (19172-47-5)
UNSPSC Code 12352005
NACRES NA.22

SAFETY

Risk and Safety Statements

Symbol(GHS)  Flame (GHS02)
GHS02
Signal word  Danger
Hazard statements  H261
Precautionary statements  P231+P232-P422
Hazard Codes  Xn-F,Xi,Xn,F
Risk 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  TSCA listed
HazardClass  4.3
PackingGroup  III
HS Code  29349990
Storage Class 4.3 - Hazardous materials which set free flammable gases upon contact with water
Hazard Classifications Water-react 2
REACH Registrations Active
Limited Quantities 0.5 Kg (1.1 lbs) (solid)
Excepted Quantities Max Inner Pack (30g or 30ml) and Max Outer Pack (500g or 500ml)
NFPA 704
2
2 1
W

Lawesson's Reagent price More Price(52)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Sigma-Aldrich 227439 Lawesson reagent 97% 19172-47-5 10g $51.3 2026-04-30 Buy
Sigma-Aldrich 227439 Lawesson reagent 97% 19172-47-5 25g $62.9 2026-04-30 Buy
TCI Chemical B1133 Lawesson's Reagent [Sulfurating Reagent] >95.0%(T) 19172-47-5 25g $40 2026-04-30 Buy
TCI Chemical B1133 Lawesson's Reagent [Sulfurating Reagent] >95.0%(T) 19172-47-5 250g $242 2026-04-30 Buy
TRC TRC-L178780-50G Lawesson’s Reagent 19172-47-5 50g $390 2026-06-03 Buy
Product number Packaging Price Buy
227439 10g $51.3 Buy
227439 25g $62.9 Buy
B1133 25g $40 Buy
B1133 250g $242 Buy
TRC-L178780-50G 50g $390 Buy

Lawesson's Reagent Chemical Properties, Uses, Production

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

Vulcanizing agents, which have recently been used to generate tropothione in situ at room temperature and capture the sulfur hybrid reagents with dienophiles.

Chemical Properties

light yellow to beige powder

Uses

Thiation reagent.

Uses

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.

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.

Synthesis

Phenol

108-95-2

Lawesson's Reagent

19172-47-5

General procedure for the synthesis of Lawson's reagent from phenol: Red phosphorus (4 g; 0.129 mol), sulfur (4 g; 0.125 mol), and phenol (4 g; 0.042 mol) were mixed and the reaction was heated at 155-158°C for 5.5 hours. After completion of the reaction, the mixture was cooled to room temperature and the resulting precipitate (5.5 g, 34% yield) was collected. The product was confirmed as p-hydroxyphenyl dithiophosphonic anhydride by melting point determination, nuclear magnetic resonance (NMR) and mass spectrometry (MS) analysis.

Solubility in organics

Lawesson's reagent is modestly sol boiling organic solvents such as toluene, chlorobenzene, anisole, dimethoxyethane.

storage

Lawesson's reagent can be stored for months at rt if moisture is excluded. Prolonged heating in solution causes decomposition (polymerization). It is toxic and should be handled under a fume hood since hazardous H2S is easily liberated with moisture.

References

[1] Patent: US2006/270635, 2006, A1. Location in patent: Page/Page column 18-19; 24

Lawesson's Reagent Preparation Products And Raw materials

Raw materials

Toluene Anisole Phosphorus pentasulfide Benzene Phenol
2,4,6,8,9,10-Hexathia-1,3,5,7-tetraphosphatricyclo[3.3.1.13,7]decane, 1,3,5,7-tetrasulfide

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Preparation Products

tert-Butyl 4-(4-formyl-1,3-thiazol-2-yl)tetrahydro-1(2H)-pyridinecarboxylate tert-Butyl 4-(5-formyl-4-methyl-1,3-thiazol-2-yl)piperidine-1-carboxylate 1,3-Benzodioxole-5-carbothioamide Thiobenzamide benzyl 4-[amino(thiocarbonyl)]piperidine-1-carboxylate

Lawesson's Reagent Suppliers

Global Suppliers ( 376)
Supplier Tel Email Country ProdList Advantage
JINAN RUIFENG PHARMACEUTICAL TECHNOLOGY CO.,LTD 18668921571 liujnlz@126.com China 22 58
Jinan Jiecheng Biotechnology Co., LTD 18669572301 695919949@qq.com China 38 58
Beijing Taiya Jie Technology Development Co., Ltd. 021-33690831-8001 13552411790;18616022633 postmaster@tyjchem.cn China 1541 55
Nanjing Tianyuexing Bio-tech Co.,Ltd. 吴经理15305186370 15305186370 david@chicopharm.com China 716 58
Fujian Jinsheng Pharmaceutical Research Co., Ltd 15860871137 Z15860871137@qq.com China 5 58
J & K SCIENTIFIC LTD. 18210857532 18210857532 jkinfo@jkchemical.com China 96815 76
Meryer (Shanghai) Chemical Technology Co., Ltd. 4006356688 18621169109 market03@meryer.com China 40202 62
Beijing Donghualituo Techonlogy Development Co.,Ltd. 010-88425576 sales@dhltchem.com China 793 59
Alfa Aesar 400-6106006 saleschina@alfa-asia.com China 30103 84
TCI (Shanghai) Development Co., Ltd. 021-67121386 Sales-CN@TCIchemicals.com China 24512 81
Supplier Advantage
JINAN RUIFENG PHARMACEUTICAL TECHNOLOGY CO.,LTD 58
Jinan Jiecheng Biotechnology Co., LTD 58
Beijing Taiya Jie Technology Development Co., Ltd. 55
Nanjing Tianyuexing Bio-tech Co.,Ltd. 58
Fujian Jinsheng Pharmaceutical Research Co., Ltd 58
J & K SCIENTIFIC LTD. 76
Meryer (Shanghai) Chemical Technology Co., Ltd. 62
Beijing Donghualituo Techonlogy Development Co.,Ltd. 59
Alfa Aesar 84
TCI (Shanghai) Development Co., Ltd. 81

Related articles

View Latest Price from Lawesson's Reagent manufacturers

Image Update time Product Price Min. Order Purity Supply Ability Manufacturer
Lawesson's Reagent pictures 2026-07-27 Lawesson's Reagent
19172-47-5
 1kg 98% 20TONS Shanghai YOUNG-CHEM Chemical Co., Ltd.
Lawesson 2021-07-02 Lawesson"s Reagent
19172-47-5
 $10.00-15.00 1KG 99%+ HPLC Zhuozhou Wenxi import and Export Co., Ltd
2,4-Bis(4-methoxyphenyl)-1,3,2,4-dithiadiphosphetane 2,4-disulfide pictures 2020-01-19 2,4-Bis(4-methoxyphenyl)-1,3,2,4-dithiadiphosphetane 2,4-disulfide
19172-47-5
 $3.00 1KG 99% 1kg,5kg,50kg Career Henan Chemical Co
  • Lawesson
  • Lawesson"s Reagent
    19172-47-5
  • $10.00-15.00
  • 99%+ HPLC
  • Zhuozhou Wenxi import and Export Co., Ltd

Lawesson's Reagent Spectrum

Lawesson's Reagent(19172-47-5)IR1Lawesson's Reagent(19172-47-5)IR2Lawesson's Reagent(19172-47-5)Raman

19172-47-5 (Lawesson's Reagent) Related Search:

Dimethyl disulfide Burgess reagent Calcium hydride Diallyl disulfide LITHIUM PERIODATE
2-Methyltetrahydrofuran 1.10-Phenanthroline BLOCKING REAGENT GE Sodium triacetoxyborohydride zinc O,O,O',O'-tetrabutyl bis(phosphorodithioate)
Tributyl(vinyl)tin NA 2,4-Bis(4-phenoxyphenyl)-1,3-dithia-2,4-diphosphetane-2,4-disulfide Phosphorus trisulfide Phenylphosphine
GGKPDLRPCHPPCHYIPRPKPR Lawesson's Reagent Lawesson Reagent

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Lawesson's Reagent ,99% 1,3-Bis(4-methoxyphenyl)-2,4-dithia-1,3-diphospha(V)cyclobutane-1,3-dithione 2,4-Bis(4-methoxyphenyl)-1,3-dithia-2,4-diphospha(V)cyclobutane-2,4-dithione 2,4-Bis(4-methoxyphenyl)-1,3-dithia-2,4-diphosphacyclobutane-2,4-dithione 2,4-Bis(p-methoxyphenyl)-1,3,2,4-dithiadiphosphetane-2,4-dithione 2,4-Bisthiolato-2,4-bis(4-methoxyphenyl)-1,3-dithia-2,4-diphospha(V)cyclobutane-2,4-diylium 2,4-Di(4-methoxyphenyl) -1,3,2lambda~5~,4lambda~5~-dithiadiphosphetane-2, 4-dithione (Lawesson's Reagent) Lawesson`s reagentsulfide dimer Lawesson reagent ,98% Lawesson reagent ,99% Lawesson Reagent, 2,4-Bis(4-methoxyphenyl)-1,3,2,4-dithiadiphosphetane 2,4-disulphide bis(4-Methoxyphenyl)-1,3,2$l^{5},4$l^{5}-dithiadiphosphetane-2,4-dithione 2,4-BIS(4-METHOXYPHENYL)-2,4-DITHIOXO-1 Lawesson reagent 97% 2,4-bis(4-methoxyphenyl)-2,4-bis(sulfanylidene)-1,3,2$l^{5},4$l^{5}-dithiadiphosphetane p-Methoxyphenylthionophosphine sulfide awesson's Reag 1,3,2,4-dithiadiphosphetane,2,4-bis(4-methoxyphenyl)-,2,4-disulfide AURORA KA-1707 4-METHOXYPHENYLTHIOPHOSPHORIC CYCLIC DI(THIOANHYDRIDE) 2,4-BIS(4-METHOXYPHENYL)-1,3,2,4-DITHIADIPHOSPHETANE-2,4-DISULFIDE 2,4-DI(4-METHOXYPHENYL)-1,3,2LAMBDA-5,4LAMBDA-5-DITHIADIPHOSPHETANE-2,4-DITHIONE P-METHOXYPHENYLTHIONOPHOSPHINE SULFIDE DIMER P-METHOXYPHENYLTHIOPHOSPHINE SULFIDE, DIMER 2,4-bis(4-methoxyphenyl)-1,3-dithia-2,4-diphosphetane 2,4-disulphide 2,4-Bis(methoxyphenyl)-1,3-dithia-2,4-diphosphetane-2,4-disulfide Lawesson's Reagent [Sulfurating Reagent] 4-methoxyphenylthionophosphine sulfide dimer 2,4-Bis(4-methoxyphenyl)-2,4-dithioxo-1,3,2,4-dithiadiphosphetane 97% 242-855-4 2,4-bis(4-methoxyphenyl)-2,4-disulfanylene-1,3,2,4-dithiadiphosphetane 2,4-BIS(4-METHOXYPHENYL)-1,3,2,4-DITHIADIPHOSPHETANE-2 Lawesson's Reagent [Sulfurating Reagent]> Lawessons Reagent,>98% awesson's Reagent Lawesson'sReagen Lawesson's Reagent ISO 9001：2015 REACH Lawesson'sReagent(LR) 2,4-bis(4-methoxyphenyl)-2,4-bis(sulfanylidene)-1,3,2 LAWESSON'S REAGENT For Synthesis Lawson’s Reagent Lawesson's Reagent bis(4-methoxyphenyl)-1,3,2lambda5,4lambda5-dithiadiphosphetane-2,4-dithione Lawesson reagent, 97% Lawesson's Reagent Lawesson's 2,4-BIS(4-METHOXYPHENYL)-1,3-DITHIA-2,4-DIPHOSPHETANE-2,4-DISULFIDE 2,4-BIS(4-METHOXYPHENYL)-2,4-DITHIOXO-1,3,2,4-DITHIADIPHOSPHETANE 4-Methoxyphenylthiophosphoric cyclic di(thioanhydride), LR, 2,4-Bis(4-methoxyphenyl)-2,4-dithioxo-1,3,2,4-dithiadiphosphetane, 2,4-Bis-(4-methoxyphenyl)-1,3-dithia-2,4-diphosphetane 2,4-disulfide Lawesson LAWESSON REAGENT LR Lawson reagent 19172-47-5 1972-47-5 C14H14O2P2S4 C14H14O2P2S2 Sulfur Compounds (for Synthesis)