1,3,5-Triaza-7-phosphaadamantane
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]
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| Names | |
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| IUPAC name
1,3,5-Triaza-7-phosphatricyclo[3.3.1.13,7]decane | |
| Other names
PTA | |
| Identifiers | |
3D model (JSmol) |
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| ChemSpider | |
| ECHA InfoCard | 100.207.239 |
PubChem CID |
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CompTox Dashboard (EPA) |
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| 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 | |
Preparation
Hexamethylenetetramine reacts with tetrakis(hydroxymethyl)phosphonium chloride, sodium hydroxide and formaldehyde in water to obtain the product.[2]
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See also
- RAPTA, a class of ruthenium complexes with the PTA ligand
References
- 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.
- 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.
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