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Propargylamine

Propargylamine
Names
Other names
  • 2-Propyn-1-amine
  • prop-2-yn-1-amine
Identifiers
ECHA InfoCard 100.017.740 Edit this at Wikidata
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).

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

Drugs

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Propargylamine is used in the synthesis of:

  1. Etintidine [69539-53-3]
  2. 2-PAT
  3. HDAC1/MAO-B-IN-1 [2759855-37-1]

References

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  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.
  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


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