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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:
19172-47-5
Peso molecular:
404.47
Beilstein/REAXYS Number:
1024888
MDL number:
MFCD00005171
UNSPSC Code:
12352005
PubChem Substance ID:
24853631
NACRES:
NA.22

Quality Level

100

assay

97%

form

powder

mp

228-230 °C (lit.)

SMILES string

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

InChI key

CFHGBZLNZZVTAY-UHFFFAOYSA-N

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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.

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.

pictograms

Flame
GHS02

signalword

Danger

hcodes

H261

Hazard Classifications

Water-react 2

supp_hazards

EUH029

Storage Class

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

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

Certificados de análisis (COA)

Busque Certificados de análisis (COA) introduciendo el número de lote del producto. Los números de lote se encuentran en la etiqueta del producto después de las palabras «Lot» o «Batch»

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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)
Jos C M Kistemaker et al.
Journal of the American Chemical Society, 139(28), 9650-9661 (2017-06-20)
Symmetric molecular motors based on two overcrowded alkenes with a notable absence of a stereogenic center show potential to function as novel mechanical systems in the development of more advanced nanomachines offering controlled motion over surfaces. Elucidation of the key
Lawesson's reagent
Nagaoka J
Journal of Synthetic Organic Chemistry, Japan, 53(12), 1138-1140 (1995)
Daniel Brayton et al.
Chemical communications (Cambridge, England), (2)(2), 206-208 (2005-12-24)
A one-pot reaction of maltol with Lawesson's reagent generates dithiomaltol, a thiopyran-4-thione, via an unusual heterocyclic atom exchange (HCAE) reaction; only pyrones with proton or aliphatic substituents undergo the HCAE substitution.
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