3-Dimethylaminoacrolein

3-Dimethylaminoacrolein
Names
	Preferred IUPAC name (2E)-3-(Dimethylamino)prop-2-enal
	Other names 3-Dimethylaminopropenal
Identifiers
CAS Number	692-32-0 ; 927-63-9 (non-specific) ;
3D model (JSmol)	Interactive image;
ChemSpider	553863;
ECHA InfoCard	100.011.962
EC Number	213-157-7;
PubChem CID	638320;
UNII	5MVV69JD7Z ;
	InChI InChI=1S/C5H9NO/c1-6(2)4-3-5-7/h3-5H,1-2H3/b4-3+ Key: RRLMPLDPCKRASL-ONEGZZNKSA-N;
	SMILES CN(C)/C=C/C=O;
Properties
Chemical formula	C5H9NO
Molar mass	99.133 g·mol−1
Appearance	Clear, faintly yellow to dark brown liquid
Density	0.99 g·cm−3 at 25°C
Boiling point	*91 °C at 0.1 kPa 133–144 °C; 270–273 °C;
Solubility in water	Soluble
Solubility in methanol, 1,2-dichloroethane	Soluble
Hazards
	GHS labelling:
Pictograms
Signal word	Danger
Hazard statements	H314
Precautionary statements	P260, P264, P280, P301+P330+P331, P303+P361+P353, P304+P340, P305+P351+P338, P310, P321, P363, P405, P501
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

3-Dimethylaminoacrolein is an organic compound with the formula Me₂NC(H)=CHCHO. It is a pale yellow water-soluble liquid. The compound has a number of useful and unusual properties. When used on mice given morphine, it can reverse the hypnotic effect of the drug, while the compound has a more stimulating effect on human subjects.

It is a stable chemical, unlike the parent compound 3-aminoacrolein, and can be used as a comparably nontoxic precursor to malondialdehyde. The compound can be thought of as vinylogous dimethylformamide (DMF) and combines the functionalities of an unsaturated aldehyde and an enamine. Therefore, 3-dimethylaminoacrolein and its vinamidines derivates can be used as molecular building blocks for the formation of nitrogen-containing heterocycles, such as pyridines, pyrimidines, pyrroles or pyrazoles.