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, e.g. it "causes a reversal of the hypnotic effect of morphine in mice" and has a "stimulating effect in humans".

It is a stable chemical, unlike the parent compound 3-aminoacrolein, and can be used as a comparably nontoxic precursor for the genotoxic, mutagenic, and potentially carcinogenic 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 vinamidines derived there from (composed of vinylogous amidines) or vinamidinium salts (substituted 1,5-diazapentadienes) can be used as reactive molecular building blocks for the formation of nitrogen-containing heterocycles, such as pyridines, pyrimidines, pyrroles or pyrazoles.