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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:
19172-47-5
Molecular Weight:
404.47
Beilstein:
1024888
MDL number:
MFCD00005171
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

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

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M de Neeling et al.
Journal of neural engineering, 16(6), 061001-061001 (2019-06-05)
Brain computer interfacing (BCI) has enjoyed increasing interest not only from research communities such as engineering and neuroscience but also from visionaries that predict it will change the way we will interact with technology. Since BCIs establish an alternative communication
Zoltán Kaleta et al.
Organic letters, 8(8), 1625-1628 (2006-04-07)
[reaction: see text] Thionation of amides, 1,4-diketones, N-(2-oxoalkyl)amides, N,N'-acylhydrazines, and acyl-protected uridines with the use of a fluorous analogue of the Lawesson's reagent leads to thioamides, thiophenes, 1,3-thiazoles, 1,3,4-thiadiazoles, and acyl-protected 4-thiouridines. The isolation of the final products in high
The direct formation of glycosyl thiols from reducing sugars allows one-pot protein glycoconjugation.
Gonçalo J L Bernardes et al.
Angewandte Chemie (International ed. in English), 45(24), 4007-4011 (2006-05-05)
Frédéric Peyrane et al.
Chemical communications (Cambridge, England), (6)(6), 736-737 (2003-04-22)
Treatment of 2'-deoxy-3',5'-dithexyldimethylsilyl-5,6-dihydrouridine with Lawesson's reagent led to the expected C4-thiolated derivative together with a number of oxathiaphosphepane isomers which resulted from the heat reversible incorporation of an AnPS2 unit within the 2'-deoxyribose moiety explaining the subsequent anomerisation of the
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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