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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

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About This Item

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

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.[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

Signal Word

Danger

Hazard Statements

Precautionary Statements

Hazard Classifications

Water-react 2

Supplementary Hazards

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


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Jos C M Kistemaker et al.
Journal of the American Chemical Society, 139(28), 9650-9661 (2017-06-20)
Symmetric molecular motors based on two overcrowded alkenes with a notable absence of a stereogenic center show potential to function as novel mechanical systems in the development of more advanced nanomachines offering controlled motion over surfaces. Elucidation of the key
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)
Lawesson's reagent
Nagaoka J
Journal of Synthetic Organic Chemistry, Japan, 53(12), 1138-1140 (1995)
Qiuping Ding et al.
Journal of combinatorial chemistry, 11(6), 1047-1049 (2009-10-15)
In the presence of Lawesson's reagent, metal-free one-pot cascade reactions of 2-iodoanilines with acid chlorides proceeded smoothly leading to 2-substituted benzothiazoles in good to excellent yields under mild conditions. Three steps were involved in the reaction process: (1) 2-iodoanilines reacted
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)

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    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

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    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

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