Skip to Content
Merck
All Photos(3)

Key Documents

View All Documentation

227439

Sigma-Aldrich

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

Sign Into View Organizational & Contract Pricing
All Photos(3)

About This Item

Empirical Formula (Hill Notation):
C14H14O2P2S4
CAS Number:
19172-47-5
Molecular Weight:
404.47
Beilstein:
1024888
MDL number:
MFCD00005171
UNSPSC Code:
12352005
PubChem Substance ID:
24853631
NACRES:
NA.22
Pricing and availability is not currently available.

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

Looking for similar products? Visit Product Comparison Guide

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.[1][2][2]

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.[3]
  • 1,3,5,2-Trithiaphosphinane-2-sulfide derivatives by reacting with benzaldehyde in the presence of trialkyl phosphite.[3]
  • 2,4,6-Triphenyl-1,3,5-trithiane from benzaldehyde and ethyl acrylate.[3]
  • 9-Benzanthronethione by thionation of 9-benzanthone oxime.[2]
  • 1,2,4-Trithiolane from 2,2,4,4-tetramethyl-3-thioxocyclobutanone S-oxide.[4]
  • Sulfur derivatives of triterpenic oxo compounds.[5]
  • Tropothione in situ at room temperature and to trap it with dieneophiles.[6]

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

Choose from one of the most recent versions:

Certificates of Analysis (COA)

Lot/Batch Number
MKCT3804
MKCB0032V
MKBV1156V
MKBP3284V
MKBK4505V

Don't see the Right Version?

If you require a particular version, you can look up a specific certificate by the Lot or Batch number.

Search for a COA

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

Customers Also Viewed

Slide 1 of 1

1 of 1

Ponceau Xylidine Dye content ≥60 %

Sigma-Aldrich

P2395

Ponceau Xylidine

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)
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.
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
View All Related Papers

Questions

1–2 of 2 Questions  

  1. How is shipping temperature determined? And how is it related to the product storage temperature?

    1 answer

    1. Products may be shipped at a different temperature than the recommended long-term storage temperature. If the product quality is sensitive to short-term exposure to conditions other than the recommended long-term storage, it will be shipped on wet or dry-ice. If the product quality is NOT affected by short-term exposure to conditions other than the recommended long-term storage, it will be shipped at ambient temperature. As shipping routes are configured for minimum transit times, shipping at ambient temperature helps control shipping costs for our customers. For more information, please refer to the Storage and Transport Conditions document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/316/622/storage-transport-conditions-mk.pdf

      Helpful?

  2. How can I determine the shelf life / expiration / retest date of this product?

    1 answer

    1. If this product has an expiration or retest date, it will be shown on the Certificate of Analysis (COA, CofA). If there is no retest or expiration date listed on the product's COA, we do not have suitable stability data to determine a shelf life. For these products, the only date on the COA will be the release date; a retest, expiration, or use-by-date will not be displayed.
      For all products, we recommend handling per defined conditions as printed in our product literature and website product descriptions. We recommend that products should be routinely inspected by customers to ensure they perform as expected.
      For products without retest or expiration dates, our standard warranty of 1 year from the date of shipment is applicable.
      For more information, please refer to the Product Dating Information document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/449/386/product-dating-information-mk.pdf

      Helpful?

Reviews

No rating value

Active Filters

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service