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Dokumente

227439

Sigma-Aldrich

Lawesson-Reagenz

97%

Synonym(e):

2,4-Bis-[4-methoxyphenyl]-1,3-dithia-2,4-diphosphetan-2,4-disulfid, 4-Methoxy-phenylthiophosphonsäure-cycl.-di-thioanhydrid, LR, Phosphorpentasulfid-Ersatz

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About This Item

Empirische Formel (Hill-System):
C14H14O2P2S4
CAS-Nummer:
19172-47-5
Molekulargewicht:
404.47
Beilstein:
1024888
MDL-Nummer:
MFCD00005171
UNSPSC-Code:
12352005
PubChem Substanz-ID:
24853631
NACRES:
NA.22

Qualitätsniveau

100

Assay

97%

Form

powder

mp (Schmelzpunkt)

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

InChIKey

CFHGBZLNZZVTAY-UHFFFAOYSA-N

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Allgemeine Beschreibung

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.

Anwendung

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.

Piktogramme

Flame
GHS02

Signalwort

Danger

H-Sätze

H261

Gefahreneinstufungen

Water-react 2

Zusätzliche Gefahrenhinweise

EUH029

Lagerklassenschlüssel

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

WGK

WGK 3

Flammpunkt (°F)

Not applicable

Flammpunkt (°C)

Not applicable

Analysenzertifikate (COA)

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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)
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
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
B G Bruinsma et al.
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To reduce widespread shortages, attempts are made to use more marginal livers for transplantation. Many of these grafts are discarded for fear of inferior survival rates or biliary complications. Recent advances in organ preservation have shown that ex vivo subnormothermic
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