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242-855-4

Lawesson's Reagent

CAS: 19172-47-5

Molecular Formula: C14H14O2P2S4

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242-855-4 - Names and Identifiers

Name Lawesson's Reagent
Synonyms 242-855-4
19172-47-5
Lawesson's Reagent
p-Methoxyphenylthionophosphine sulfide dimer
2,4-Bis(p-methoxyphenyl)-1,3,2,4-dithiadiphosphetane-2,4-dithione
2,4-bis(4-methoxyphenyl)-1,3,2,4-dithiadiphosphetane 2,4-disulfide
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)-1,3-dithia-2,4-diphosphetane-2,4-disulfide
1,3,2,4-Dithiadiphosphetane, 2,4-bis(4-methoxyphenyl)-, 2,4-disulfide
2,4-Bis(4-methoxyphenyl)-1,3-dithia-2,4-diphosphacyclobutane-2,4-dithione
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-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)
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
CAS 19172-47-5
EINECS 242-855-4
InChI InChI=1/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

242-855-4 - Physico-chemical Properties

Molecular FormulaC14H14O2P2S4
Molar Mass404.47
Density1.48±0.1 g/cm3(Predicted)
Melting Point228-230°C(lit.)
Boling Point525.8±60.0 °C(Predicted)
Flash Point271.8°C
Water SolubilityDecomposition
Vapor Presure1.28E-10mmHg at 25°C
AppearancePowder
ColorWhite to almost white
Merck14,5391
BRN1024888
Storage ConditionInert atmosphere,2-8°C
SensitiveMoisture Sensitive
Refractive Index1.705

242-855-4 - Risk and Safety

Hazard SymbolsXn - Harmful
Harmful
F,Xi,Xn,F -
Risk CodesR20/21/22 - Harmful by inhalation, in contact with skin and if swallowed.
R15/29 -
R37 - Irritating to the respiratory system
Safety DescriptionS8 - Keep container dry.
S43 - In case of fire use ... (there follows the type of fire-fighting equipment to be used.)
S36/37 - Wear suitable protective clothing and gloves.
S22 - Do not breathe dust.
S38 - In case of insufficient ventilation, wear suitable respiratory equipment.
S7/8 -
UN IDs3278
WGK Germany3
FLUKA BRAND F CODES13-21
TSCAYes
HS Code29349990
Hazard Class4.3
Packing GroupIII

242-855-4 - Reference Information

EPA chemical information Information provided by: ofmpub.epa.gov (external link)
Chemical reagent Lawson reagent is also called Lloyd's reagent. It is a chemical reagent commonly used to produce organic sulfur compounds. It is a yellowish solid powder at room temperature and pressure., Has a strong and unpleasant smell of decay. In 1956, it was first produced by the reaction of aromatic hydrocarbons and tetraphosphorus decasulfide. Swedish chemist Sven-Olov Lawesson carefully studied its reaction with organic compounds, which greatly promoted its application, so the name was derived from this. The molecule of Lawson's reagent contains a four-membered ring structure composed of alternating sulfur and phosphorus. Depolymerization occurs when heated, resulting in two unstable thiophosphorus ylides (R-PS2), which are the main reactive intermediates. When reacting with two Lawson reagents with different substituents, molecules with substituents exchanged were observed in the 31NMR spectrum of the product, thus confirming the existence of intermediate R-PS2.
Lawson reagent is an oxygen-sulfur exchange reagent. The most common application is the preparation of thioamides, which converts carbonyl compounds into thiocarbonyl compounds. The substrates that can react include ketones, esters, lactones, and amides., Lactams, quinones, etc. Electron-rich carbonyl groups are easier to react. When responding with α,β-unsaturated aldehydes and ketones, the double bonds are not affected.
Related chemical reactions 1, aliphatic, aromatic and heterocyclic aromatic primary amides can react well with Lawson's reagent. Tetraphosphorus decasulfide is also a commonly used vulcanization reagent, but its use sometimes causes the amide to decompose to produce nitrile and hydrogen sulfide, thereby reducing the reaction yield.
2. The mixture of silver perchlorate and Lawson's reagent can be used as an oxyphilic Lewis acid to catalyze the Diels-Alder reaction of diolefins and α,β-unsaturated aldehydes.
3,1, 4-dione reacts with Lawson reagent to cyclization into thiophene. It can also be reacted with tetraphosphorus decasulfide, but the reaction requires a higher temperature.
4, Lawson reagent reacts with sulfoxide to generate thioproduct, and then desulfurization to generate thioether. Therefore, it can be used as a reducing agent for sulfoxide.
5. The reaction yield of Lawson's reagent with an amide with a hydroxyl or amino group at the ortho position on the benzene ring is not high, because the following by-products are generated. This reaction can be used for the preparation of thiomonoalkyl phosphonates.
Related reagents Many compounds similar to Lawson's reagent have been prepared. They are easier to use than Lawson's reagent, the reaction conditions are mild, and the yield is relatively high. After the methoxyphenyl group is replaced by an alkyl group (such as methyl, ethyl, isopropyl, butyl) sulfur group, the reagent formed is called Davy reagent (DR), and when the substituent is phenyl sulfur group, it is called Japanese reagent (JR), when it is p-phenoxyphenyl, it is called Belleau reagent (BR). They can all be prepared from corresponding mercaptans and tetraphosphorus decasulfide.
use vulcanization reagent, recently used for sulfur hybrid reagent that generates tropothione in situ at room temperature and uses diene affinity capture.
Last Update：2024-04-09 21:21:28
242-855-4
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Jiangsu Pules Biotechnology Co.,Ltd.
Product Name: Lawesson's Reagent Request for quotation
CAS: 19172-47-5
Tel: 17505222756
Email: pules.cn@gmail.com
Mobile: +86-17551318830
CHEMBSF (Shanghai) Biomedical Technology Co., Ltd
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Product Name: Lawesson's Reagent Request for quotation
CAS: 19172-47-5
Tel: +86-18721521379
Email: 18721521379@163.com
Mobile: +86-18721521379
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Nantong Reform Petro-Chemical CO., LTD.
Spot supply
Product Name: Lawesson's Reagent Request for quotation
CAS: 19172-47-5
Tel: +86-17551318830
Email: r@reformchem.com­
Mobile: +86-17551318830
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SKYRUN INDUSTRIAL CO.,LTD
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Product Name: Lawesson's Reagent Visit Supplier Webpage Request for quotation
CAS: 19172-47-5
Tel: +86 0571-86722205
Email: sales@chinaskyrun.com
Mobile: +8618958170122
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SHANGHAI ACMEC BIOCHEMICAL TECHNOLOGY CO., LTD.
Spot supply
Product Name: Lawesson reagent Visit Supplier Webpage Request for quotation
CAS: 19172-47-5
Tel: +86-400-900-4166
Email: product@acmec-e.com
Mobile: +86-18621343501
QQ: 2881950922 Click to send a QQ message
Wechat: 18621343501
WhatsApp: +86-18621343501
Hefei TNJ Chemical Industry Co.,Ltd.
Product Name: Lawesson's Reagent Request for quotation
CAS: 19172-47-5
Tel: 0086-551-65418684
Email: sales@tnjchem.com
　　　　 info@tnjchem.com
Mobile: 0086 189 4982 3763
QQ: 2881500840 Click to send a QQ message
Wechat: 189 4982 3763
WhatsApp: 0086 189 4982 3763
Product List: View Catalog
Shanghai Macklin Biochemical Co., Ltd
Spot supply
Product Name: Lawesson reagent Visit Supplier Webpage Request for quotation
CAS: 19172-47-5
Tel: +86-18821248368
Email: Int06@meryer.com
Mobile: +86-18821248368
QQ: 495145328 Click to send a QQ message
WhatsApp: +86-18821248368
Shanghai Worldyang Chemical Co.,Ltd.
Product Name: bis(4-methoxyphenyl)-1,3,2lambda5,4lambda5-dithiadiphosphetane-2,4-dithione Request for quotation
CAS: 19172-47-5
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View History
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