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Key Documents

Autres documents

227439

Sigma-Aldrich

Lawesson reagent

97%

Synonyme(s) :

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, 4-Methoxyphenylthiophosphoric cyclic di(thioanhydride), LR

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About This Item

Formule empirique (notation de Hill):
C14H14O2P2S4
Numéro CAS:
19172-47-5
Poids moléculaire :
404.47
Numéro Beilstein :
1024888
Numéro MDL:
MFCD00005171
Code UNSPSC :
12352005
ID de substance PubChem :
24853631
Nomenclature NACRES :
NA.22

Niveau de qualité

100

Pureté

97%

Forme

powder

Pf

228-230 °C (lit.)

Chaîne SMILES 

COc1ccc(cc1)P2(=S)SP(=S)(S2)c3ccc(OC)cc3

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

Clé InChI

CFHGBZLNZZVTAY-UHFFFAOYSA-N

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Description générale

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.

Application

Lawesson reagent can be used as a reagent to synthesize:
  • Oxthiaphosphinine-3-sulfide derivatives by the reaction with Mannich bases of β-naphthol and 8-hydroxyquinoline.
  • 1,3,5,2-Trithiaphosphinane-2-sulfide derivatives by reacting with benzaldehyde in the presence of trialkyl phosphite.
  • 2,4,6-Triphenyl-1,3,5-trithiane from benzaldehyde and ethyl acrylate.
  • 9-Benzanthronethione by thionation of 9-benzanthone oxime.
  • 1,2,4-Trithiolane from 2,2,4,4-tetramethyl-3-thioxocyclobutanone S-oxide.
  • Sulfur derivatives of triterpenic oxo compounds.
  • Tropothione in situ at room temperature and to trap it with dieneophiles.

Pictogrammes

Flame
GHS02

Mention d'avertissement

Danger

Mentions de danger

H261

Conseils de prudence

P231 + P232 - P422

Classification des risques

Water-react 2

Risques supp

EUH029

Code de la classe de stockage

4.3 - Hazardous materials which set free flammable gases upon contact with water

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

Certificats d'analyse (COA)

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Journal of combinatorial chemistry, 11(6), 1047-1049 (2009-10-15)
In the presence of Lawesson's reagent, metal-free one-pot cascade reactions of 2-iodoanilines with acid chlorides proceeded smoothly leading to 2-substituted benzothiazoles in good to excellent yields under mild conditions. Three steps were involved in the reaction process: (1) 2-iodoanilines reacted
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The reaction between N-nitrosamides and 2,4-bis(4-methoxyphenyl)-1,3,2,4-dithiadiphosphetane-2,4-disulfide (LR) at low temperature (20-50 degrees C) gives the corresponding thioamides as the main products. In the reaction between N-nitroso-2-pyrrolidone and LR, dihydro-2-(3H)-thiophenone (III) is also isolated. Mechanistic considerations for the formation of III
Synthesis of 1, 2, 4-trithiolanes from thione S-oxides and Lawesson reagent at room temperature
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Bulletin of the Chemical Society of Japan, 77(1), 187-188 (2004)
A novel protocol for the generation of tropothione and its trapping with electron deficient dienophiles
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Tetrahedron Letters, 47(52), 9329-9329 (2006)
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