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227439

Sigma-Aldrich

Lawesson reagent

97%

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Synonym(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
Empirical Formula (Hill Notation):
C14H14O2P2S4
CAS Number:
Molecular Weight:
404.47
Beilstein/REAXYS Number:
1024888
MDL number:
PubChem Substance ID:
NACRES:
NA.22

Quality Level

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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1 of 4

This Item
22089230471PHL82880
vibrant-m

227439

Lawesson reagent

vibrant-m

220892

1,4-Butanediol diglycidyl ether

vibrant-m

30471

Davy-reagent p-tolyl

vibrant-m

PHL82880

Nordihydroguaiaretic acid

assay

97%

assay

≥95%

assay

≥97.0%

assay

≥98.0% (HPLC)

mp

228-230 °C (lit.)

mp

-

mp

209-213 °C (dec.)

mp

184-186 °C (lit.)

form

powder

form

liquid

form

-

form

-

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

signalword

Danger

hcodes

Hazard Classifications

Water-react 2

supp_hazards

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


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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)
Lawesson's reagent
Nagaoka J
Journal of Synthetic Organic Chemistry, Japan, 53(12), 1138-1140 (1995)
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)
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
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

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