Diisopropylphosphate

Diisopropylphosphate
Names
Preferred IUPAC name
Di(propan-2-yl) hydrogen phosphate
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.015.048
KEGG
MeSH Diisopropylphosphate
UNII
  • InChI=1S/C6H15O4P/c1-5(2)9-11(7,8)10-6(3)4/h5-6H,1-4H3,(H,7,8) checkY
    Key: WZPMZMCZAGFKOC-UHFFFAOYSA-N checkY
  • CC(C)OP(=O)(O)OC(C)C
  • O=P(OC(C)C)(OC(C)C)O
Properties
C6H15O4P
Molar mass 182.156 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Diisopropylphosphate (DIPP) is an organophosphate compound with the chemical formula C6H15O4P. It is a phosphate monoester and acts as an acetylcholinesterase inhibitor through covalent interaction with the enzyme.[1]

Chemistry

Diisopropylphosphate consists of two isopropoxy groups attached to a phosphate group. It is the conjugate base of diisopropyl hydrogen phosphate and is structurally related to a number of organophosphorus compounds, including diisopropyl fluorophosphate.[1]

Biological significance

Diisopropylphosphate is formed during the hydrolysis of diisopropyl fluorophosphate (DFP), a potent organophosphorus acetylcholinesterase inhibitor. The enzyme diisopropyl-fluorophosphatase catalyzes the conversion of DFP to diisopropylphosphate and fluoride ions.[2]

See also

References

  1. 1 2 PubChem. "Diisopropyl phosphate". pubchem.ncbi.nlm.nih.gov. Retrieved 2026-06-04.
  2. ↑ Cohen, J. A.; Warringa, M. G. P. J. "Purification and properties of dialkylfluorophosphatase". Biochimica et Biophysica Acta. 26 (1): 29.39 – via Netherlands Organisation for Applied Scientific Research.