Lawesson's reagent

Lawesson's reagent (LR) is a chemical compound used in organic synthesis as a thiation agent. Lawesson's reagent was first made popular by Sven-Olov Lawesson, who did not, however, invent it. Lawesson's reagent was first made in 1956 during a systematic study of the reactions of arenes with P4S10.

Lawesson's reagent
Names
IUPAC name
2,4-Bis(4-methoxyphenyl)-1,3,2,4-dithiadiphosphetane-2,4-disulfide
Preferred IUPAC name
2,4-Bis(4-methoxyphenyl)-1,3,2,4-dithiadiphosphetane-2,4-dithione
Other names
Lawesson reagent; LR
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.038.944
EC Number
  • 242-855-4
UNII
  • 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 Y
    Key: CFHGBZLNZZVTAY-UHFFFAOYSA-N Y
  • InChI=1/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
    Key: CFHGBZLNZZVTAY-UHFFFAOYAB
  • S=P1(SP(=S)(S1)c2ccc(OC)cc2)c3ccc(OC)cc3
Properties
C14H14O2P2S4
Molar mass 404.45 g·mol−1
Appearance Slightly yellow powder
Melting point 228–231 °C (442–448 °F; 501–504 K)
Insoluble
Hazards
GHS labelling:
Warning
H261, H302, H312, H332
P231+P232, P261, P264, P270, P271, P280, P301+P312, P302+P352, P304+P312, P304+P340, P312, P322, P330, P363, P370+P378, P402+P404, P501
Related compounds
Related thiation agents
 Hydrogen sulfide,
Phosphorus pentasulfide
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Y verify (what is YN ?)
Infobox references
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