All Photos(3)
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:
1024888
MDL number:
UNSPSC Code:
12352005
PubChem Substance ID:
NACRES:
NA.22
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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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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.
Signal Word
Danger
Hazard Statements
Precautionary Statements
Hazard Classifications
Water-react 2
Supplementary Hazards
WGK
WGK 3
Flash Point(F)
Not applicable
Flash Point(C)
Not applicable
Certificates of Analysis (COA)
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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)
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)
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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.
Nicola Barban et al.
Nature genetics, 48(12), 1462-1472 (2016-11-01)
The genetic architecture of human reproductive behavior-age at first birth (AFB) and number of children ever born (NEB)-has a strong relationship with fitness, human development, infertility and risk of neuropsychiatric disorders. However, very few genetic loci have been identified, and
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