Lawesson's Reagent

description reactions similar products Uses

Product Name: Lawesson's Reagent
CAS No.: 19172-47-5
Chemical Name: Lawesson's Reagent
Synonyms: LAWESSON REAGENT;LR;242-855-4;Lawesson's;Lawesson`s reagentsulfide dimer;2,4-BIS(4-METHOXYPHENYL)-2,4-DITHIOXO-1,3,2,4-DITHIADIPHOSPHETANE;2,4-BIS(4-METHOXYPHENYL)-1,3,2,4-DITHIADIPHOSPHETANE-2,4-DISULFIDE;2,4-BIS(4-METHOXYPHENYL)-1,3-DITHIA-2,4-DIPHOSPHETANE-2,4-DISULFIDE;awesson's Reag;AURORA KA-1707
CBNumber: CB8128537
Molecular Formula: C14H14O2P2S4
Formula Weight: 404.47
MOL File: 19172-47-5.mol

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Lawesson's Reagent Property

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)
EPA Substance Registry System: 1,3,2,4-Dithiadiphosphetane, 2,4-bis(4-methoxyphenyl)-, 2,4-disulfide (19172-47-5)

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Safety

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: Yes
HazardClass: 4.3
PackingGroup: III
HS Code: 29349990

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Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Danger

Hazard statements

H261In contact with water releases flammable gas

Precautionary statements

P231+P232Handle under inert gas. Protect from moisture.

P422Store contents under …

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N-Bromosuccinimide Price

Sigma-Aldrich

Product number: 227439
Product name: Lawesson reagent
Purity: 97%
Packaging: 10g
Price: $46.8
Updated: 2024/03/01

Sigma-Aldrich

Product number: 227439
Product name: Lawesson reagent
Purity: 97%
Packaging: 25g
Price: $57.2
Updated: 2024/03/01

TCI Chemical

Product number: B1133
Product name: Lawesson's Reagent [Sulfurating Reagent]
Purity: >95.0%(T)
Packaging: 25g
Price: $40
Updated: 2024/03/01

TCI Chemical

Product number: B1133
Product name: Lawesson's Reagent [Sulfurating Reagent]
Purity: >95.0%(T)
Packaging: 250g
Price: $242
Updated: 2024/03/01

Alfa Aesar

Product number: A14530
Product name: Lawesson's Reagent, 97%
Packaging: 5g
Price: $19
Updated: 2024/03/01

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Lawesson's Reagent Chemical Properties,Usage,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

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.

Uses

Thiation reagent.

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.

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.

Lawesson's Reagent Preparation Products And Raw materials

Raw materials

Toluene Anisole Phosphorus pentasulfide Benzene

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

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Lawesson's Reagent Suppliers

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View Lastest Price from Lawesson's Reagent manufacturers

Zhuozhou Wenxi import and Export Co., Ltd

Product: Lawesson"s Reagent 19172-47-5
Price: US $15.00-10.00/KG
Min. Order: 1KG
Purity: 99%+ HPLC
Supply Ability: Monthly supply of 1 ton
Release date: 2021-06-27

Career Henan Chemical Co

Product: 2,4-Bis(4-methoxyphenyl)-1,3,2,4-dithiadiphosphetane 2,4-disulfide 19172-47-5
Price: US $3.00/KG
Min. Order: 1KG
Purity: 99%
Supply Ability: 1kg,5kg,50kg
Release date: 2020-01-18

19172-47-5, Lawesson's ReagentRelated Search:

Diallyldisulfide 1.10-Phenanthroline BLOCKING REAGENT GE Sodium triacetoxyborohydride 2-Methyltetrahydrofuran CALCIUM HYDRIDE LITHIUM PERIODATE Dimethyl disulfide Burgess reagent zinc O,O,O',O'-tetrabutyl bis(phosphorodithioate) Tributyl(vinyl)tin NA PHOSPHORUS TRISULFIDE Phenyl phosphine 2,4-BIS(4-PHENOXYPHENYL)-1,3-DITHIA-2,4-DIPHOSPHETANE-2,4-DISULFIDE GGKPDLRPCHPPCHYIPRPKPR Lawesson's Reagent Lawesson Reagent

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'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

LR

LAWESSON REAGENT

AURORA KA-1707

4-METHOXYPHENYLTHIOPHOSPHORIC CYCLIC DI(THIOANHYDRIDE)

2,4-BIS(4-METHOXYPHENYL)-1,3,2,4-DITHIADIPHOSPHETANE-2,4-DISULFIDE

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

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]

Lawesson's

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]&gt

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

19172-47-5

1972-47-5

C14H14O2P2S4

C14H14O2P2S2

Sulfur Compounds (for Synthesis)

Dithietanes

Simple 4-Membered Ring Compounds

Synthetic Reagents

C-X Bond Formation (Non-Halogen)