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CAS RN: 19172-47-5 | Product Number: B1133

Lawesson's Reagent [Sulfurating Reagent]


Purity: >93.0%(T)
Synonyms:
  • 2,4-Bis(4-methoxyphenyl)-1,3-dithia-2,4-diphosphetane 2,4-Disulfide
Product Documents:
25G
$40.00
9   10   ≥100 
250G
$242.00
Contact Us 1   ≥40 

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Product Number B1133
Purity / Analysis Method >93.0%(T)
Molecular Formula / Molecular Weight C__1__4H__1__4O__2P__2S__4 = 404.45 
Physical State (20 deg.C) Solid
Storage Temperature Room Temperature (Recommended in a cool and dark place, <15°C)
Store Under Inert Gas Store under inert gas
Condition to Avoid Moisture Sensitive
CAS RN 19172-47-5
Reaxys Registry Number 1024888
PubChem Substance ID 87564076
Merck Index (14) 5391
MDL Number

MFCD00005171

Specifications
Appearance White to Light yellow to Green powder to crystal
Purity(Iodometric Titration) min. 93.0 %
Properties (reference)
Melting Point 230 °C
GHS
Pictogram Pictogram
Signal Word Warning
Hazard Statements H302 + H332 : Harmful if swallowed or if inhaled.
H315 : Causes skin irritation.
H319 : Causes serious eye irritation.
Precautionary Statements P501 : Dispose of contents/ container to an approved waste disposal plant.
P261 : Avoid breathing dust/ fume/ gas/ mist/ vapors/ spray.
P270 : Do not eat, drink or smoke when using this product.
P271 : Use only outdoors or in a well-ventilated area.
P264 : Wash skin thoroughly after handling.
P280 : Wear protective gloves/ eye protection/ face protection.
P337 + P313 : If eye irritation persists: Get medical advice/ attention.
P305 + P351 + P338 : IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.
P302 + P352 : IF ON SKIN: Wash with plenty of soap and water.
P332 + P313 : If skin irritation occurs: Get medical advice/ attention.
P362 : Take off contaminated clothing and wash before reuse.
P301 + P312 + P330 : IF SWALLOWED: Call a POISON CENTER/doctor if you feel unwell. Rinse mouth.
P304 + P340 + P312 : IF INHALED: Remove person to fresh air and keep comfortable for breathing. Call a POISON CENTER/doctor if you feel unwell.
Related Laws:
Transport Information:
HS Number 2931.49.0080
Application
TCI Practical Example: Conversion of Carbonyl Group into Thiocarbonyl Group using Lawesson's Reagent

Used Chemicals

Procedure

To a solution of Lawesson’s reagent (2.38 g, 5.88 mmol) in dichloromethane (42 mL), 2-pyrrolidone (1.0 g, 11.75 mmol) in dichloromethane (42 mL) was added at room temperature under N2 atmosphere. After stirring the reaction solution for 2 hours, the solvent was removed under reduced pressure and the residue was purified by column chromatography (hexane:ethyl acetate = 9:1 - 6:4), giving pyrrolidine-2-thione as a white solid (0.79 g, 66%).

Experimenter’s Comments

The reaction was carried out in the fume hood due to Lawesson’s reagent’s bad smell.
The reaction mixture was monitored by TLC (hexane:ethyl acetate = 3:2, Rf = 0.28).

Analytical Data(pyrrolidine-2-thione)

1H NMR (400 MHz, CDCl3); δ 8.61 (brs, 1H), 3.61 (t, 2H, J = 8.0 Hz), 2.86 (t, 2H, J = 8.0 Hz), 2.20-2.12 (m, 2H).

13C NMR (101 MHz, CDCl3); δ 205.83, 49.66, 43.21, 22.91.

Lead Reference


Application
Thiocarbonylation Reagent

References

  • S. O. Lawesson, et al., Bull. Soc. Chim. Belg. 1978, 87, 223; 87, 229; 87, 293; 87, 299.
  • R. Shabana, et al., Nouv. J. Chim. 1980, 4, 47.


PubMed Literature


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