Chemistry:Propargylamine

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Propargylamine
Propargyl amine.svg
Names
Other names
  • 2-Propyn-1-amine
  • prop-2-yn-1-amine
Identifiers
Properties
C3H5N
Molar mass 55.080 g·mol−1
Appearance colorless liquid
Density 0.867 g/cm3
Boiling point 83 °C (181 °F; 356 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Propargylamine is an organic compound with the formula HC≡CCH2NH2. It is a colorless, odorless liquid that is used as a precursor to other compounds.[1] Propargyl amines are produced by reactions of amines with propargyl halides.

The behavior of propargyl amine is illustrated by its acylation benzoyl chloride to the amide. A Sonogashira coupling of the terminal alkyne end with another equivalent of benzoylchloride gives the dicarbonyl, a precursor to an oxazole.[2]

oxazoline from propargyl amides Merkul 2006

References

  1. Lauder, Kate; Toscani, Anita; Scalacci, Nicolò; Castagnolo, Daniele (2017). "Synthesis and Reactivity of Propargylamines in Organic Chemistry". Chemical Reviews 117 (24): 14091–14200. doi:10.1021/acs.chemrev.7b00343. PMID 29166000. https://kclpure.kcl.ac.uk/portal/en/publications/synthesis-and-reactivity-of-propargylamines-in-organic-chemistry(47919fe8-e7fc-4b3b-9296-e921fcf9673f).html. 
  2. A new consecutive three-component oxazole synthesis by an amidation–coupling–cycloisomerization (ACCI) sequence Eugen Merkul and Thomas J. J. Müller Chem. Commun., 2006, 4817 - 4819, doi:10.1039/b610839c