Propargylamine

Propargylamine
Names
	Other names 2-Propyn-1-amine; prop-2-yn-1-amine;
Identifiers
CAS Number	2450-71-7;
3D model (JSmol)	Interactive image;
ChEMBL	ChEMBL3263480;
ChemSpider	208829;
ECHA InfoCard	100.017.740
EC Number	219-513-8;
PubChem CID	239041;
CompTox Dashboard (EPA)	DTXSID30862951 ;
	InChI InChI=1S/C3H5N/c1-2-3-4/h1H,3-4H2 Key: JKANAVGODYYCQF-UHFFFAOYSA-N;
	SMILES C#CCN;
Properties
Chemical formula	C3H5N
Molar mass	55.080 g·mol−1
Appearance	colorless liquid
Density	0.867 g/cm3
Boiling point	83 °C (181 °F; 356 K)
Refractive index (nD)	1.449
Hazards
	GHS labelling:
Pictograms
Signal word	Danger
Hazard statements	H225, H302, H310, H314
Precautionary statements	P210, P233, P240, P241, P242, P243, P260, P262, P264, P264+P265, P270, P280, P301+P317, P301+P330+P331, P302+P352, P302+P361+P354, P303+P361+P353, P304+P340, P305+P354+P338, P316, P317, P321, P330, P361+P364, P363, P370+P378, P403+P235, P405, P501
Flash point	6 °C (43 °F; 279 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

Drugs

Propargylamine is used in the synthesis of:

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

References

↑ 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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[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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Drugs

References