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19172-47-5 - Lawesson's Reagent, 97% - 2,4-Bis(4-methoxyphenyl)-2,4-dithioxo-1,3,2,4-dithiadiphosphetane - 4-Methoxyphenylthionophosphine sulfide dimer - A14530 - Alfa Aesar

A14530 Lawesson's Reagent, 97%

CAS-Nummer
19172-47-5
Synonyme
2,4-Bis(4-methoxyphenyl)-2,4-dithioxo-1,3,2,4-dithiadiphosphetane
4-Methoxyphenylthionophosphine sulfide dimer

Größe Preis ($) Menge Verfügbarkeit
5g 10,08
25g 28,74
100g 93,60
500g 360,80
Zum Warenkorb hinzufügen Zur Angebotsanfrage hinzufügen Artikel anzeigen

Lawesson's Reagent, 97%

MDL
MFCD00005171
EINECS
242-855-4

Chemische Eigenschaften

Formel
C14H14O2P2S4
Molmasse
404.47
Schmelzpunkt
221-225°
Sensitivität
Moisture Sensitive
Löslichkeit
Insoluble in water.

Anwendungen

Lawesson's reagent is a thiation agent used to convert carbonyl compounds into thiocarbonyls. It is also used to thionate enones, esters, lactones, amides, lactams and quinones. Further, it is used to prepare thiols from alcohols. It is associated with silver perchlorate and utilized as and oxophilic Lewis acid catalyst for Diels-Alder reaction of dienes with alfa, beta-unsaturated aldehydes.

Bemerkungen

Incompatible with strong oxidizing agents.

Literaturverweise

Powerful thionation agent used for the replacement of the carbonyl oxygen of ketones, amides and esters, by sulfur: Bull. Soc. Chim. Belg., 87, 223, 229, 293, 299, 525 (1978); Tetrahedron, 35, 1339, 2433 (1979). Review: Tetrahedron, 41, 5061 (1985). For conversion of N-methylpyrrolidinone to the thiolactam, see: Org. Synth. Coll., 7, 372 (1990).

Uracil and its derivatives are thionated selectively at the 4-position: Synthesis, 152 (1988). Peptides give endo-thiopeptides: Tetrahedron, 37, 3635 (1981). Esters, orthoesters, acetals and epoxides give the thio-analogues: Monatsh. Chem., 115, 769 (1984). Used, in combination with 1,1,3,3-Tetramethyl­thiourea, L13392, for formation of bis-thioesters for subsequent radical coupling as a method of ring formation in Nicolaou's syntheses of hemibrevitoxin B and brevitoxin B: J. Am. Chem. Soc., 115, 3558 (1993); 117, 10227 (1995).

Reaction with 1,4-diketones gives 2,5-disubstituted thiophenes in high yield: Synthesis, 1061 (1982).

Reaction with ɑ-diazo ketones has been used to prepare 1,2,3-thiadiazoles: Heterocycles, 19, 241 (1982).

Benzylic and related alcohols are converted to the corresponding thiols: J. Chem. Soc., Chem. Commun., 205 (1989); J. Chem. Soc., Perkin 1, 1113 (1993).

Reacts with N-protected amino acids to give mixed anhydrides, useful in peptide coupling: Tetrahedron, 38, 3267 (1982). See Appendix 6.

Has also been found to act as an efficient trapping agent for 1,3-dipoles under very mild conditions. Its powerful dipolarophile character allows it to be used as a "1,3-dipole indicator" even with dipoles of low reactivity, the outcome of the reaction being readily verified by 31P NMR: J. Org. Chem., 60, 3904 (1995).

Kayukova, L. A.; Praliyev, K. D.; Gut’yar, V. G.; Baitursynova, G. P. Modification of organic compounds with Lawesson’s reagent. Russ. J. Org. Chem. 2015, 51 (2), 148-160.

Gholinejad, M. One-Pot Copper-Catalysed Thioetherification of Aryl Halides Using Alcohols and Lawesson's Reagent in Diglyme. Eur. J. Org. Chem. 2015, 2015 (19), 4162-4167.

GHS Gefahren- und Sicherheitshinweise

Gefahrenhinweise (EU): H331-H302-H315-H319-H335-H261

Toxic if inhaled. Harmful if swallowed. Causes skin irritation. Causes serious eye irritation. May cause respiratory irritation. In contact with water releases flammable gas.

Sicherheitshinweise: P231+P232-P261-P280-P305+P351+P338-P304+P340-P311-P362-P301+P312-P405-P501a

Handle under inert gas. Protect from moisture. Avoid breathing dust/fume/gas/mist/vapours/spray. Wear protective gloves/protective clothing/eye protection/face protection. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. IF INHALED: Remove to fresh air and keep at rest in a position comfortable for breathing. Call a POISON CENTER or doctor/physician. Take off contaminated clothing and wash before reuse. IF SWALLOWED: Call a POISON CENTER or doctor/physician if you feel unwell. Store locked up. Dispose of contents/container in accordance with local/regional/national/international regulations.

Weitere Referenzen

Merck
14,5391
Beilstein
1024888
Gefahrenklasse
4.3
Verpackungsgruppe
III
Harmonized Tariff Code
2934.99
TSCA
Yes

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