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.
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Other names
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| Identifiers | |
| ECHA InfoCard | 100.017.740 |
PubChem CID
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CompTox Dashboard (EPA)
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| 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).
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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]
Drugs
editPropargylamine is used in the synthesis of:
- Etintidine [69539-53-3]
- 2-PAT
- HDAC1/MAO-B-IN-1 [2759855-37-1]
References
edit- ^ 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.
- ^ 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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