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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%

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

Dimensioni Prezzo ($) Quantità Disponibilità
5g 11,00
25g 28,50
100g 103,00
500g 446,00
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Lawesson's Reagent, 97%

MDL
MFCD00005171
EINECS
242-855-4

Proprietà chimiche

Formula
C14H14O2P2S4
Peso formula
404.47
Punto di fusione
221-225°
Sensibilità
Moisture Sensitive
Solubilità
Insoluble in water.

Applicazioni

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.

Note

Incompatible with strong oxidizing agents.

Letteratura

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.

Rischio GHS e dichiarazioni precauzionali

Dichiarazioni di rischio (UE): 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.

Dichiarazioni precauzionali: 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.

Altri riferimenti

Merck
14,5391
Beilstein
1024888
Classe di rischio
4.3
Gruppo di imballaggio
III
Codice tariffe armonizzato
2934.99
TSCA
Yes

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