1,3,5-Triaza-7-phosphaadamantane

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1,3,5‐Triaza‐7‐phosphaadamantane.svg
Names
Preferred IUPAC name
1,3,5-Triaza-7-phosphaadamantane
Other names
PTA
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.207.239 Edit this at Wikidata
  • InChI=1S/C6H12N3P/c1‐7‐2‐9‐3‐8(1)5‐10(4‐7)6‐9/h1‐6H2
    Key: FXXRPTKTLVHPAR‐UHFFFAOYSA‐N
  • C1N2CN3CN1CP(C2)C3
Properties
C6H12N3P
Molar mass 157.157 g·mol−1
Melting point 260 °C (533 K)[1]
23.5 g[1]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

1,3,5-Triaza-7-phosphaadamantane (PTA) is a chemical compound with the formula C6H12N3P, a product of the substitution of a nitrogen atom of hexamethylenetetramine with a phosphorus atom. It is soluble in water, methanol, trichloromethane, acetone, ethanol and DMSO, insoluble in hydrocarbon solvent.[1] As a reagent in organic synthesis, it is used as a ligand for transition metal complexes and as a catalyst for Baylis–Hillman reactions.[1]

Preparation[edit]

Hexamethylenetetramine reacts with tetrakis(hydroxymethyl)phosphonium chloride, sodium hydroxide and formaldehyde in water to obtain the product.[2]

See also[edit]

  • RAPTA, a class of ruthenium complexes with the PTA ligand

References[edit]

  1. ^ a b c d Luca Gonsalvi; Maurizio Peruzzini (2010-10-15). 1,3,5-Triaza-7-phosphaadamantane (PTA). John Wiley & Sons, Ltd. doi:10.1002/047084289x.rn01186. ISBN 9780471936237.
  2. ^ Donald J. Daigle; Tara J. Decuir; Jeffrey B. Robertson; Donald J. Darensbourg (2007-01-05). 1,3,5-Triaz-7-Phosphatricyclo[3.3.1.1 3,7 ]Decane and Derivatives. John Wiley & Sons, Inc. pp. 40–45. doi:10.1002/9780470132630.ch6. ISBN 9780470132630.