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MedKoo Cat#: 598485 | Name: Lawesson's reagent
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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Lawesson's reagent is a thiation agent.

Chemical Structure

Lawesson's reagent
Lawesson's reagent
CAS#19172-47-5

Theoretical Analysis

MedKoo Cat#: 598485

Name: Lawesson's reagent

CAS#: 19172-47-5

Chemical Formula: C14H14O2P2S4

Exact Mass: 403.9352

Molecular Weight: 404.45

Elemental Analysis: C, 41.58; H, 3.49; O, 7.91; P, 15.32; S, 31.71

Price and Availability

Size Price Availability Quantity
25g USD 350.00 2 Weeks
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Synonym
Lawesson's reagent; NSC 150550; NSC-150550; NSC150550;
IUPAC/Chemical Name
2,4-bis(4-methoxyphenyl)-1,3,2,4-dithiadiphosphetane 2,4-disulfide
InChi Key
CFHGBZLNZZVTAY-UHFFFAOYSA-N
InChi Code
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
SMILES Code
COC1=CC=C(P2(SP(S2)(C3=CC=C(OC)C=C3)=S)=S)C=C1
Appearance
Solid powder
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO
Shelf Life
>3 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.03.00
More Info
Product Data
Product Data
Instruction
View handling instruction
Biological target:
Lawesson's reagent is a thiation agent.
In vitro activity:
The reaction proceeded via deoxygenation of azlactones by Lawesson's reagent without metal or external additives. Reference: Org Biomol Chem. 2022 Dec 14;20(48):9589-9592. https://pubmed.ncbi.nlm.nih.gov/36408836/
In vivo activity:
The effects of the slow-releasing (GYY4137) and spontaneous H2S donors (Na2S and Lawesson's reagent, LR) were evaluated in histamine and compound 48/80 (C48/80)-dependent dorsal skin pruritus and inflammation in male BALB/c mice. Na2S and LR (Lawesson’s reagent) significantly ameliorated histamine or C48/80-induced pruritus and inflammation, although these effects were less pronounced or absent with GYY4137. Reference: Pharmacol Res. 2017 Jan;115:255-266. https://pubmed.ncbi.nlm.nih.gov/27840098/

Preparing Stock Solutions

The following data is based on the product molecular weight 404.45 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol:
1. Yin G, Wang X, Wang Y, Shi T, Zeng Y, Wang Y, Peng X, Wang Z. Lawesson's reagent promoted deoxygenation of azlactones for the syntheses of 2,4-disubstituted thiazoles. Org Biomol Chem. 2022 Dec 14;20(48):9589-9592. doi: 10.1039/d2ob01939f. PMID: 36408836. 2. Salojärvi E, Peuronen A, Sapkota N, Lehtonen A. Reactions of a Dioxidomolybdenum(VI) Complex with Thionation Reagents-Formation of Mo(IV) Species with Sulfur Donors. Molecules. 2022 Oct 22;27(21):7154. doi: 10.3390/molecules27217154. PMID: 36363980; PMCID: PMC9655758. 3. Rodrigues L, Ekundi-Valentim E, Florenzano J, Cerqueira AR, Soares AG, Schmidt TP, Santos KT, Teixeira SA, Ribela MT, Rodrigues SF, de Carvalho MH, De Nucci G, Wood M, Whiteman M, Muscará MN, Costa SK. Protective effects of exogenous and endogenous hydrogen sulfide in mast cell-mediated pruritus and cutaneous acute inflammation in mice. Pharmacol Res. 2017 Jan;115:255-266. doi: 10.1016/j.phrs.2016.11.006. Epub 2016 Nov 10. PMID: 27840098. 4. Medeiros JV, Bezerra VH, Gomes AS, Barbosa AL, Lima-Júnior RC, Soares PM, Brito GA, Ribeiro RA, Cunha FQ, Souza MH. Hydrogen sulfide prevents ethanol-induced gastric damage in mice: role of ATP-sensitive potassium channels and capsaicin-sensitive primary afferent neurons. J Pharmacol Exp Ther. 2009 Sep;330(3):764-70. doi: 10.1124/jpet.109.152801. Epub 2009 Jun 2. PMID: 19491326.
In vitro protocol:
1. Yin G, Wang X, Wang Y, Shi T, Zeng Y, Wang Y, Peng X, Wang Z. Lawesson's reagent promoted deoxygenation of azlactones for the syntheses of 2,4-disubstituted thiazoles. Org Biomol Chem. 2022 Dec 14;20(48):9589-9592. doi: 10.1039/d2ob01939f. PMID: 36408836. 2. Salojärvi E, Peuronen A, Sapkota N, Lehtonen A. Reactions of a Dioxidomolybdenum(VI) Complex with Thionation Reagents-Formation of Mo(IV) Species with Sulfur Donors. Molecules. 2022 Oct 22;27(21):7154. doi: 10.3390/molecules27217154. PMID: 36363980; PMCID: PMC9655758.
In vivo protocol:
1. Rodrigues L, Ekundi-Valentim E, Florenzano J, Cerqueira AR, Soares AG, Schmidt TP, Santos KT, Teixeira SA, Ribela MT, Rodrigues SF, de Carvalho MH, De Nucci G, Wood M, Whiteman M, Muscará MN, Costa SK. Protective effects of exogenous and endogenous hydrogen sulfide in mast cell-mediated pruritus and cutaneous acute inflammation in mice. Pharmacol Res. 2017 Jan;115:255-266. doi: 10.1016/j.phrs.2016.11.006. Epub 2016 Nov 10. PMID: 27840098. 2. Medeiros JV, Bezerra VH, Gomes AS, Barbosa AL, Lima-Júnior RC, Soares PM, Brito GA, Ribeiro RA, Cunha FQ, Souza MH. Hydrogen sulfide prevents ethanol-induced gastric damage in mice: role of ATP-sensitive potassium channels and capsaicin-sensitive primary afferent neurons. J Pharmacol Exp Ther. 2009 Sep;330(3):764-70. doi: 10.1124/jpet.109.152801. Epub 2009 Jun 2. PMID: 19491326.
1: Nicolau LA, Silva RO, Damasceno SR, Carvalho NS, Costa NR, Aragão KS, Barbosa AL, Soares PM, Souza MH, Medeiros JV. The hydrogen sulfide donor, Lawesson's reagent, prevents alendronate-induced gastric damage in rats. Braz J Med Biol Res. 2013 Aug;46(8):708-14. doi: 10.1590/1414-431X20133030. Epub 2013 Aug 16. PubMed PMID: 23969974; PubMed Central PMCID: PMC3854416. 2: Kumar SV, Parameshwarappa G, Ila H. Synthesis of 2,4,5-trisubstituted thiazoles via Lawesson's reagent-mediated chemoselective thionation-cyclization of functionalized enamides. J Org Chem. 2013 Jul 19;78(14):7362-9. doi: 10.1021/jo401208u. Epub 2013 Jul 10. PubMed PMID: 23815778. 3: Huang P, Zhang R, Liang Y, Dong D. Lawesson's reagent-initiated domino reaction of aminopropenoyl cyclopropanes: synthesis of thieno[3,2-c]pyridinones. Org Biomol Chem. 2012 Feb 28;10(8):1639-44. doi: 10.1039/c2ob06709a. Epub 2012 Jan 11. PubMed PMID: 22234526. 4: Qiu G, Hu Y, Ding Q, Peng Y, Hu X, Wu J. Synthesis of 4-methylene-4H-benzo[d][1,3]thiazines via a tandem reaction of 1-(2-alkynylphenyl)ketoximes with Lawesson's reagent. Chem Commun (Camb). 2011 Sep 14;47(34):9708-10. doi: 10.1039/c1cc12937f. Epub 2011 Jul 27. PubMed PMID: 21792441. 5: Brayton D, Jacobsen FE, Cohen SM, Farmer PJ. A novel heterocyclic atom exchange reaction with Lawesson's reagent: a one-pot synthesis of dithiomaltol. Chem Commun (Camb). 2006 Jan 14;(2):206-8. Epub 2005 Nov 17. PubMed PMID: 16372107. 6: Ju J, McKenna CE. Synthesis of oligodeoxyribonucleoside phosphorothioates using Lawesson's reagent for the sulfur transfer step. Bioorg Med Chem Lett. 2002 Jun 17;12(12):1643-5. PubMed PMID: 12039581. 7: Kayukova L, Praliyev K, Kemelbekov U, Abdildanova A, Gutyar V. Interaction of the O-Benzoyl-β-aminopropioamidoximes with Lawesson's Reagent and Spectral Characterization of the Products. ISRN Org Chem. 2012 Mar 22;2012:945893. doi: 10.5402/2012/945893. eCollection 2012. PubMed PMID: 24052857; PubMed Central PMCID: PMC3765757. 8: Kaschel J, Schmidt CD, Mumby M, Kratzert D, Stalke D, Werz DB. Donor-acceptor cyclopropanes with Lawesson's and Woollins' reagents: formation of bisthiophenes and unprecedented cage-like molecules. Chem Commun (Camb). 2013 May 14;49(39):4403-5. doi: 10.1039/c2cc37631h. Epub 2012 Dec 18. PubMed PMID: 23247108. 9: Ishii A, Yamashita R, Saito M, Nakayama J. Deoxygenation of dithiirane 1-oxides with Lawesson's reagent leading to the corresponding dithiiranes. J Org Chem. 2003 Feb 21;68(4):1555-8. PubMed PMID: 12585902. 10: Kaleta Z, Makowski BT, Soós T, Dembinski R. Thionation using fluorous Lawesson's reagent. Org Lett. 2006 Apr 13;8(8):1625-8. PubMed PMID: 16597126. 11: Legnani L, Toma L, Caramella P, Chiacchio MA, Giofrè S, Delso I, Tejero T, Merino P. Computational Mechanistic Study of Thionation of Carbonyl Compounds with Lawesson's Reagent. J Org Chem. 2016 Sep 2;81(17):7733-40. doi: 10.1021/acs.joc.6b01420. Epub 2016 Aug 5. PubMed PMID: 27459366. 12: Aragoni MC, Arca M, Blake AJ, Lippolis V, Schröder M, Wilson C. 4-Methoxyphenylphosphonic acid: reactivity of Lawesson's reagent. Acta Crystallogr C. 2002 May;58(Pt 5):o260-2. Epub 2002 Apr 11. PubMed PMID: 11983984. 13: Ozturk T, Ertas E, Mert O. Use of Lawesson's reagent in organic syntheses. Chem Rev. 2007 Nov;107(11):5210-78. Epub 2007 Sep 15. PubMed PMID: 17867708. 14: Ding Q, Huang XG, Wu J. Facile synthesis of benzothiazoles via cascade reactions of 2-iodoanilines, acid chlorides and Lawesson's reagent. J Comb Chem. 2009 Nov-Dec;11(6):1047-9. doi: 10.1021/cc900085p. PubMed PMID: 19824656. 15: Kaleta Z, Tarkanyi G, Gömöry A, Kalman F, Nagy T, Soós T. Synthesis and application of a fluorous Lawesson's reagent: convenient chromatography-free product purification. Org Lett. 2006 Mar 16;8(6):1093-5. PubMed PMID: 16524276. 16: Rao Y, Li X, Nagorny P, Hayashida J, Danishefsky SJ. A Simple Method for the Conversion of Carboxylic Acids into Thioacids with Lawesson's Reagent. Tetrahedron Lett. 2009 Dec 2;50(48):6684-6686. PubMed PMID: 20160926; PubMed Central PMCID: PMC2762222. 17: Medeiros JV, Bezerra VH, Gomes AS, Barbosa AL, Lima-Júnior RC, Soares PM, Brito GA, Ribeiro RA, Cunha FQ, Souza MH. Hydrogen sulfide prevents ethanol-induced gastric damage in mice: role of ATP-sensitive potassium channels and capsaicin-sensitive primary afferent neurons. J Pharmacol Exp Ther. 2009 Sep;330(3):764-70. doi: 10.1124/jpet.109.152801. Epub 2009 Jun 2. PubMed PMID: 19491326. 18: Nakai T, McDowell CA. Determination of spin parameters reflected in the nuclear magnetic resonance powder patterns for two equivalent 31P nuclei in Lawesson's reagent. Solid State Nucl Magn Reson. 1995 Mar;4(3):163-71. PubMed PMID: 7773649. 19: Peyrane F, Fourrey JL, Clivio P. Thiation of 2'-deoxy-5,6-dihydropyrimidine nucleosides with Lawesson's reagent: characterisation of oxathiaphosphepane intermediates. Chem Commun (Camb). 2003 Mar 21;(6):736-7. PubMed PMID: 12703798. 20: Mohamed NR, Elmegeed GA, Abd-ElMalek HA, Younis M. Synthesis of biologically active steroid derivatives by the utility of Lawesson's reagent. Steroids. 2005 Mar;70(3):131-6. PubMed PMID: 15763590.

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