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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:
1314-80-3
Molecular Weight:
222.27
EC Number:
215-242-4
MDL number:
MFCD00011441
UNSPSC Code:
12352303
PubChem Substance ID:
329752397
NACRES:
NA.21

Quality Level

200

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 Classifications

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

Supplementary Hazards

EUH029

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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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)
Thiation with phosphorus pentasulfide in pyridine solution.
Klingsberg E and Papa D.
Journal of the American Chemical Society, 73(10), 4988-4989 (1951)
Phosphorus (V) sulfide.
Edmondson SD and Sannigrahi M.
e-EROS Encyclopedia of Reagents for Organic Synthesis. (2004)

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