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Merck

227439

Sigma-Aldrich

Lawesson reagent

97%

Sinónimos:

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

Fórmula empírica (notación de Hill):
C14H14O2P2S4
Número de CAS:
Peso molecular:
404.47
Beilstein:
1024888
Número MDL:
Código UNSPSC:
12352005
ID de la sustancia en PubChem:
NACRES:
NA.22

Nivel de calidad

Análisis

97%

formulario

powder

mp

228-230 °C (lit.)

cadena 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

Clave InChI

CFHGBZLNZZVTAY-UHFFFAOYSA-N

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Descripción general

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.

Aplicación

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.

Pictogramas

Flame

Palabra de señalización

Danger

Frases de peligro

Consejos de prudencia

Clasificaciones de peligro

Water-react 2

Riesgos supl.

Código de clase de almacenamiento

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

Clase de riesgo para el agua (WGK)

WGK 3

Punto de inflamabilidad (°F)

Not applicable

Punto de inflamabilidad (°C)

Not applicable


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Qiuping Ding et al.
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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K A Jørgensen et al.
IARC scientific publications, (41)(41), 159-168 (1982-01-01)
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
Okuma K, et al.
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
Nair V, et al.
Tetrahedron Letters, 47(52), 9329-9329 (2006)

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