bis(4-methoxyphenyl)-1,3,2λ5,4λ5-dithiadiphosphetane-2,4-dithione

• ChemBase ID: 90001
• Molecular Formular: C14H14O2P2S4
• Molecular Mass: 404.467282
• Monoisotopic Mass: 403.93518695
• SMILES: S1P(=S)(c2ccc(cc2)OC)SP1(=S)c1ccc(cc1)OC
• Canonical SMILES: COc1ccc(cc1)P1(=S)SP(=S)(S1)c1ccc(cc1)OC
• InChI: 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
• InChIKey: CFHGBZLNZZVTAY-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: bis(4-methoxyphenyl)-1,3,2λ^5,4λ^5-dithiadiphosphetane-2,4-dithione; bis(4-methoxyphenyl)-1,3,2$l^{5},4$l^{5}-dithiadiphosphetane-2,4-dithione
• IUPAC Traditional name: lawesson's reagent
• Synonyms: 2,4-bis(4-methoxyphenyl)-1,3,2,4-dithiadiphosphetane 2,4-disulfide; 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); Lawesson reagent; Lawesson Reagent; 2,4-Bis(4-methoxyphenyl)-1,3,2,4-dithiadiphosphetane 2,4-disulphide; 2,4-Bis(4-methoxyphenyl)-2,4-dithioxo-1,3,2,4-dithiadiphosphetane 97%; LR; Lawesson's reagent; Lawesson's Reagent; 2,4-bis(4-METHOXYPHENYL)-1,3-DITHIA-2-4-DIPHOSPHETANE 2,4-DISULFIDE; Lawesson reagent; 4-Methoxyphenylthionophosphine sulfide dimer; Lawesson's Reagent; 4-甲氧基苯基硫代磷环二(硫代酸酐); Lawesson 试剂; 劳氏试剂

Database IDs

• CAS Number: 19172-47-5
• EC Number: 242-855-4
• MDL Number: MFCD00005171
• Beilstein Number: 1024888
• Merck Index: 145391
• PubChem SID: 24853631; 24874849; 162076856
• PubChem CID: 87949
• Chemspider ID: 79346
• Wikipedia Title: Lawesson's_reagent

CALCULATED PROPERTIES

• H Acceptors: 2
• H Donor: 0
• LogD (pH = 5.5): 5.2936
• LogD (pH = 7.4): 5.2936
• Log P: 5.2936
• Molar Refractivity: 104.6542 cm^3
• Polarizability: 43.731716 Å^3
• Polar Surface Area: 18.46 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Insoluble in water
• Apperance: Slightly yellow powder
• Melting Point: 221-225°C; 228 - 231 °C; 228-230 °C; 228-230 °C(lit.); 228-230°C
• Density: , solid

Safety Information

• Storage Condition: Room Temperature (15-30°C), Desiccate, Store Under Nitrogen
• Storage Warning: Moisture Sensitive; Toxic/Highly Flammable/Store under Nitrogen/Moisture Sensitive
• European Hazard Symbols: Flammable (F); Harmful (XN); Irritant; X; Harmful (Xn)
• UN Number: UN3134
• German water hazard class: 3
• Hazard Class: 4.3
• Packing Group: III
• Risk Statements: 15/29; 15/29 20/21/22; 15/29-20/22-36/37/38; R:22
• Safety Statements: 22 45 7/8; 7/8-43; 7/8-9-26-33-36/37-43; S:36/37/39
• TSCA Listed: 是
• GHS Pictograms: GHS02; GHS06
• GHS Signal Word: Danger
• GHS Hazard statements: H261; H331-H302-H315-H319-H335-H261
• GHS Precautionary statements: P231 + P232-P422; P231+P232-P305+P351+P338-P302+P352-P321-P405-P501A
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Supplemental Hazard Statements: Contact with water liberates toxic gas.

Product Information

• Purity: ≥98.0% (S); 97%
• Grade: purum
• Empirical Formula (Hill Notation): C14H14O2P2S4

DETAILS

MP Biomedicals - 02155434

(Lawesson's Reagent)

Sigma Aldrich - 227439

Application
Thiation reagent used recently to generate tropothione in situ at room temperature and trapping it with dieneophiles.1
Packaging
10, 25, 100 g in glass bottle

Sigma Aldrich - 61750

Other Notes
The most efficient thiation reagent known till now, used for the thiation of carboxamides, ketones, lactones and imides, lactames, 3-oxocarboxylic derivatives (amides, esters and nitriles) and thio-S-esters1; Selective thionation of oligopeptides2,3; Reviews about LR4,5

REFERENCES

• 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 alcoholsare 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).