227439

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

Properties

• 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

Description

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.

Safety Information

• pictograms: GHS02
• signalword: Danger
• hcodes: H261
• pcodes: P231 + P232 - P422
• Hazard Classifications: Water-react 2
• supp_hazards: EUH029
• 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