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See also: Phosphoramides
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 mass95.042 g·mol−1
Appearancewhite solid
good
Acidity (pKa)<3.6[1]
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 formulaO=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

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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:[2]

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

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

Phosphoramides

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Main article: Phosphoramides

Phosphoramide is also the parent compound for a range of derivatives called phosphoramides.[3] An example compound is the polar solvent hexamethylphosphoramide (HMPA).

References

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  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
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  • Wikimedia Commons logo Media related to phosphoramides at Wikimedia Commons
  • Wiktionary logo The dictionary definition of phosphoramide at Wiktionary

📚 Artikel Terkait di Wikipedia

Hexamethylphosphoramide

Hexamethylphosphoramide, often abbreviated HMPA, is a phosphoramide (an amide of phosphoric acid) with the formula [(CH3)2N]3PO. This colorless liquid

Phosphoramides

Phosphoramides are a class of phosphorus compounds with the formula O=P(NR2)3-n(OH)n. They can be considered derivatives of phosphoric acid where OH groups

Cyclophosphamide

due to its metabolite phosphoramide mustard. This metabolite is only formed in cells that have low levels of ALDH. Phosphoramide mustard forms DNA crosslinks

Metepa

aphoxide METEPA Trimethylaziridinylphosphine oxide MAPO Tris(1,2-propylene)phosphoramide Tris(2-methyl-1-aziridinyl)phosphine oxide Identifiers CAS Number 57-39-6 Y

Urea

halide Iodide Acyl halide Chloride Perchlorate Other Isothiocyanate Phosphoramides Sulfenyl chloride Sulfonamide Thiocyanate Sulfinylamines See also chemical

Phosphoryl group

chloride (O=P(−Cl)3), methylphosphonyl dichloride (O=P(−CH3)(−Cl)2) and phosphoramide (O=P(−NH2)3). A phosphoryl group should not be confused with a phosphate

Nitrogen mustard

Barsky D, Colvin ME, et al. (December 1995). "A structural basis for a phosphoramide mustard-induced DNA interstrand cross-link at 5'-d(GAC)". Proc. Natl

Benzene

halide Iodide Acyl halide Chloride Perchlorate Other Isothiocyanate Phosphoramides Sulfenyl chloride Sulfonamide Thiocyanate Sulfinylamines See also chemical