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232106

Sigma-Aldrich

Phosphorus pentasulfide

99%

Synonym(s):

Phosphorus(V) sulfide

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About This Item

Empirical Formula (Hill Notation):
P2S5
CAS Number:
Molecular Weight:
222.27
EC Number:
MDL number:
UNSPSC Code:
12352303
PubChem Substance ID:
NACRES:
NA.21

Quality Level

Assay

99%

form

powder

bp

514 °C

mp

280-284 °C (lit.)

density

2.09 g/mL at 25 °C (lit.)

SMILES string

S=P(=S)SP(=S)=S

InChI

1S/P2S5/c3-1(4)7-2(5)6

InChI key

HWVAJUNEPOKXLF-UHFFFAOYSA-N

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General description

Phosphorus pentasulfide is also referred to as phosphorus(V) sulfide. It is widely employed as a thiating, deoxygenating and dehydrating agent in various organic reactions. It readily transforms esters to dithioesters.

Application

Phosphorus pentasulfide may be employed in the preparation of the following:
  • Bandgap polymer poly(isothianaphthene).
  • 3,5-diiodo-2-thiopyridone and 3,5-diiodo-4-thiopyridone.
  • Phosphorus pentasulfide can also be used:,In the conversion of carbonyls to thiocarbonyls.
  • To activate alcohols and carboxylic acid.
  • To convert furan to thiophene.

Signal Word

Danger

Hazard Statements

Hazard Classifications

Acute Tox. 4 Inhalation - Acute Tox. 4 Oral - Aquatic Acute 1 - Flam. Sol. 1 - Water-react 1

Supplementary Hazards

Storage Class Code

4.3 - Hazardous materials which set free flammable gases upon contact with water

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable


Certificates of Analysis (COA)

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Phosphorus (V) sulfide.
Edmondson SD and Sannigrahi M.
e-EROS Encyclopedia of Reagents for Organic Synthesis. (2004)
Thiation with phosphorus pentasulfide in pyridine solution.
Klingsberg E and Papa D.
Journal of the American Chemical Society, 73(10), 4988-4989 (1951)
New synthetic routes to poly (isothianaphthene) I. Reaction of phthalic anhydride and phthalide with phosphorus pentasulfide.
van Asselt R, et al.
Synthetic Metals, 74(1), 65-70 (1995)
Oriane Della-Negra et al.
Scientific reports, 10(1), 13545-13545 (2020-08-13)
The insecticide chlordecone has been used in the French West Indies for decades, resulting in long term pollution, human health problems and social crisis. In addition to bacterial consortia and Citrobacter sp.86 previously described to transform chlordecone into three families

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