Skip to Content
Merck
All Photos(3)

Documents

227439

Sigma-Aldrich

Lawesson reagent

97%

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

Sign Into View Organizational & Contract Pricing
All Photos(3)

About This Item

Empirical Formula (Hill Notation):
C14H14O2P2S4
CAS Number:
19172-47-5
Molecular Weight:
404.47
Beilstein:
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

Looking for similar products? Visit Product Comparison Guide

Related Categories

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

Signal Word

Danger

Hazard Statements

H261

Precautionary Statements

P231 + P232 - P422

Hazard Classifications

Water-react 2

Supplementary Hazards

EUH029

Storage Class Code

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

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

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)
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.
American journal of transplantation : official journal of the American Society of Transplantation and the American Society of Transplant Surgeons, 14(6), 1400-1409 (2014-04-25)
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
View All Related Papers

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service