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227439

Lawesson reagent

Name: Lawesson reagent
Brand: ALDRICH

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

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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

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Properties

Quality Level

100

assay

90%

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.

pictograms

GHS02

signalword

Danger

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

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A novel heterocyclic atom exchange reaction with Lawesson's reagent: a one-pot synthesis of dithiomaltol.

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)

Determination of spin parameters reflected in the nuclear magnetic resonance powder patterns for two equivalent 31P nuclei in Lawesson's reagent.

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

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Global Trade Item Number

SKU	GTIN
227439-10G	04061838780751
227439-100G	04061838780744
227439-25G	04061838780768