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Lawesson's Reagent

description reactions similar products Uses
Lawesson's Reagent
Lawesson's Reagent structure
CAS No.
19172-47-5
Chemical Name:
Lawesson's Reagent
Synonyms
LR;Lawesson's;AURORA KA-1707;LAWESSON REAGENT;LAWESSON'S REAGENT;Lawesson reagent 97%;Lawesson reagent ,98%;Lawesson reagent ,99%;Lawesson's Reagent ,99%;Lawesson`s reagentsulfide dimer
CBNumber:
CB8128537
Molecular Formula:
C14H14O2P2S4
Formula Weight:
404.47
MOL File:
19172-47-5.mol

Lawesson's Reagent Properties

Melting point:
228-230 °C(lit.)
storage temp. 
water-free area
form 
Powder
color 
White to almost white
Water Solubility 
Decomposition
Sensitive 
Moisture Sensitive
Merck 
14,5391
BRN 
1024888
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)
SAFETY
  • Risk and Safety Statements
  • Hazard and Precautionary Statements (GHS)
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
13-21
TSCA  Yes
HazardClass  4.3
PackingGroup  III
HS Code  29349990
Symbol(GHS):
Signal word: Danger
Hazard statements:
Code Hazard statements Hazard class Category Signal word Pictogram P-Codes
H261 In contact with water releases flammable gas Substances And Mixtures Which, In Contact With Water,Emit Flammable Gases Category 2
Category 3
Danger
Warning
P231+P232, P280, P370+P378,P402+P404, P501
H302 Harmful if swallowed Acute toxicity,oral Category 4 Warning P264, P270, P301+P312, P330, P501
H315 Causes skin irritation Skin corrosion/irritation Category 2 Warning P264, P280, P302+P352, P321,P332+P313, P362
H319 Causes serious eye irritation Serious eye damage/eye irritation Category 2A Warning P264, P280, P305+P351+P338,P337+P313P
H331 Toxic if inhaled Acute toxicity,inhalation Category 3 Danger P261, P271, P304+P340, P311, P321,P403+P233, P405, P501
H335 May cause respiratory irritation Specific target organ toxicity, single exposure;Respiratory tract irritation Category 3 Warning
Precautionary statements:
P261 Avoid breathing dust/fume/gas/mist/vapours/spray.
P264 Wash hands thoroughly after handling.
P264 Wash skin thouroughly after handling.
P270 Do not eat, drink or smoke when using this product.
P271 Use only outdoors or in a well-ventilated area.
P280 Wear protective gloves/protective clothing/eye protection/face protection.
P231+P232 Handle under inert gas. Protect from moisture.
P305+P351+P338 IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.
P405 Store locked up.
P422 Store contents under …
P501 Dispose of contents/container to..…

Lawesson's Reagent price More Price(9)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Sigma-Aldrich 227439 Lawesson reagent 97% 19172-47-5 10g $20.9 2018-11-13 Buy
Sigma-Aldrich 227439 Lawesson reagent 97% 19172-47-5 25g $33.6 2018-11-13 Buy
TCI Chemical B1133 Lawesson's Reagent [Sulfurating Reagent] >95.0%(T) 19172-47-5 25g $28 2018-11-22 Buy
TCI Chemical B1133 Lawesson's Reagent [Sulfurating Reagent] >95.0%(T) 19172-47-5 250g $210 2018-11-22 Buy
Alfa Aesar A14530 Lawesson's Reagent, 97% 19172-47-5 5g $11.2 2018-11-13 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.

Lawesson's Reagent Preparation Products And Raw materials

Raw materials

Preparation Products


Lawesson's Reagent Suppliers

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Lawesson's Reagent Spectrum


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