Skip to Content
Merck
CN

227439

Lawesson reagent

90%

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 In to View Organizational & Contract Pricing.

Select a Size

About This Item

Empirical Formula (Hill Notation):
C14H14O2P2S4
CAS Number:
19172-47-5
Molecular Weight:
404.47
UNSPSC Code:
12352005
NACRES:
NA.22
PubChem Substance ID:
24853631
MDL number:
MFCD00005171
Beilstein/REAXYS Number:
1024888
Assay:
90%
Form:
powder

Key Documents

View All Documentation
Technical Service
Need help? Our team of experienced scientists is here for you.
Let Us Assist
Technical Service
Need help? Our team of experienced scientists is here for you.
Let Us Assist

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

SMILES string

COc1ccc(cc1)P2(=S)SP(=S)(S2)c3ccc(OC)cc3

InChI key

CFHGBZLNZZVTAY-UHFFFAOYSA-N

assay

90%

form

powder

Quality Level

100

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

signalword

Danger

hcodes

H261

supp_hazards

EUH029

Storage Class

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

Hazard Classifications

Water-react. 2

Choose from one of the most recent versions:

Certificates of Analysis (COA)

Lot/Batch Number
MKDB2894
MKCZ5219
MKCT3804
0000085310
0000065853

Don't see the Right Version?

If you require a particular version, you can look up a specific certificate by the Lot or Batch number.

Search for a COA

Already Own This Product?

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

Visit the Document Library

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.
Reaction of lupane and oleanane triterpenoids with Lawesson's reagent
Kvasnica M, et al.
Tetrahedron, 64(17), 3736-3743 (2008)
T Nakai et al.
Solid state nuclear magnetic resonance, 4(3), 163-171 (1995-03-01)
The nuclear magnetic resonance (NMR) powder patterns observed for the 31P spin pair in Lawesson's reagent (1) were analyzed. Using an efficient procedure, wide ranges of the spin parameters were examined to determine whether they might reproduce the experimental one-dimensional
Juan Fortea et al.
Lancet (London, England), 395(10242), 1988-1997 (2020-07-01)
Alzheimer's disease and its complications are the leading cause of death in adults with Down syndrome. Studies have assessed Alzheimer's disease in individuals with Down syndrome, but the natural history of biomarker changes in Down syndrome has not been established.
Use of Lawesson's reagent in organic syntheses.
Turan Ozturk et al.
Chemical reviews, 107(11), 5210-5278 (2007-09-18)
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