Phosphoramide

Phosphoramide
Names
IUPAC name
Phosphoric triamide
Other names
  • Diaminophosphorylamine
  • Phosphoric amide
  • Phosphoryl triamide
  • Triaminophosphine oxide
Identifiers
3D model (JSmol)
ChemSpider
UNII
  • InChI=1S/H6N3OP/c1-5(2,3)4/h(H6,1,2,3,4)
    Key: DMSZORWOGDLWGN-UHFFFAOYSA-N
  • InChI=1/H6N3OP/c1-5(2,3)4/h(H6,1,2,3,4)
    Key: DMSZORWOGDLWGN-UHFFFAOYAP
  • NP(=O)(N)N
Properties
O=P(NH2)3
Molar mass 95.042 g·mol−1
Appearance white solid
good
Acidity (pKa) <3.6
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Phosphoramide is a chemical compound with the molecular formula O=P(NH2)3. It is a derivative of phosphoric acid in which each of the hydroxyl groups have been replaced with an amino group. In bulk, the compound is a white solid which is soluble in polar solvents.

Chemical properties

Phosphoramide arises from the reaction of phosphoryl chloride with ammonia. In moist air, it hydrolyzes to an ammonium salt:

2 H2O + O=P(NH2)3 → [NH4]+[PO2(OH)(NH2)]− + NH3

It reacts with sodium hydroxide with loss of ammonia:

NaOH + O=P(NH2)3 → Na+[PO2(NH2)2]− + NH3

The related thiophosphoryl triamide [Wikidata] compound S=P(NH2)3 was made from the reaction of thiophosphoryl chloride with ammonia.

Phosphoramides

Phosphoramide is also the parent compound for a range of derivatives called phosphoramides. An example compound is the polar solvent hexamethylphosphoramide (HMPA).

References

  1. ↑ Perrin, D. D., ed. (1982) [1969]. Ionisation Constants of Inorganic Acids and Bases in Aqueous Solution. IUPAC Chemical Data (2nd ed.). Oxford: Pergamon (published 1984). Entry 186. ISBN 0-08-029214-3. LCCN 82-16524.
  2. ↑ Robert Klement; Otto Koch (1954). "Phosphoroxy‐triamid und Phosphorthio‐triamid". Chemische Berichte. 87 (3): 333–340. doi:10.1002/cber.19540870308.
  3. ↑ IUPAC, Compendium of Chemical Terminology, 5th ed. (the "Gold Book") (2025). Online version: (2006–) "phosphoramides". doi:10.1351/goldbook.A00484