3-Dimethylaminoacrolein

3-Dimethylaminoacrolein
Names
Preferred IUPAC name
(2E)-3-(Dimethylamino)prop-2-enal
Other names
3-Dimethylaminopropenal
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.011.962 Edit this at Wikidata
EC Number
  • 213-157-7
UNII
  • InChI=1S/C5H9NO/c1-6(2)4-3-5-7/h3-5H,1-2H3/b4-3+
    Key: RRLMPLDPCKRASL-ONEGZZNKSA-N
  • CN(C)/C=C/C=O
Properties
C5H9NO
Molar mass 99.133 g·mol−1
Appearance Clear, faintly yellow[1] to dark brown liquid[2]
Density 0.99 g·cm−3 at 25°C[1]
Boiling point *91 °C at 0.1 kPa[1]
  • 133–144 °C[3]
  • 270–273 °C[2]
Soluble[3]
Solubility in methanol,[4] 1,2-dichloroethane[5] Soluble
Hazards
GHS labelling:
GHS05: Corrosive
Danger
H314
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).

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".[3]

It is a stable chemical, unlike the parent compound 3-aminoacrolein [ru],[6] and can be used as a comparably nontoxic precursor for the genotoxic, mutagenic, and potentially carcinogenic malondialdehyde.[7] 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)[8] can be used as reactive molecular building blocks for the formation of nitrogen-containing heterocycles, such as pyridines, pyrimidines, pyrroles or pyrazoles.[9]

  1. ^ a b c "3-(Dimethylamino)acrolein 927-63-9 | TCI Deutschland GmbH". www.tcichemicals.com (in German). Retrieved 2018-01-14.
  2. ^ a b Sigma-Aldrich Co., product no. 305839.
  3. ^ a b c DE 944852, F. Wille, "Verfahren zur Herstellung von Derivaten des 3-Amino-acroleins", published 1956-06-28, assigned to Badische Anilin- & Soda-Fabrik AG 
  4. ^ DE 2424373, M. Decker, W. Schönleben, H. Toussaint, H. Hoffmann, "Verfahren zur Herstellung von Derivaten des Malondialdehyds", published 1975-12-11, assigned to BASF AG 
  5. ^ US 5780622, D. Dolphin, R. Boyle, "Methods of synthesizing 5,15-diarylbenzochlorine-7-one", published 1998-07-14, assigned to The University of British Columbia 
  6. ^ Thummel, Randolph P. (2001). "(Z)-β-Aminoacrolein". Encyclopedia of Reagents for Organic Synthesis. doi:10.1002/047084289X.ra087. ISBN 0-471-93623-5.
  7. ^ L.J. Niederhofer; J.S. Daniels; C.A. Rouzer; R.E. Greene; L.J. Marnett (2003), "Malondialdehyde, a product of lipid peroxidation, is mutagenic in human cells", J. Biol. Chem., vol. 278, no. 33, pp. 31426–31433, doi:10.1074/jbc.M212549200, PMID 12775726
  8. ^ D. Lloyd; H. McNab (1976), "Vinamidine and Vinamidinium-Salze – Beispiele für stabilisierte Push-Pull-Alkene", Angew. Chem., vol. 88, no. 15, pp. 496–504, doi:10.1002/ange.19760881503
  9. ^ S. Makhseed; H.M.E. Hassaneen; M.H. Elnagdi (2007), "Studies with 2-(Arylhydrazono)aldehydes: Synthesis and Chemical Reactivity of Mesoxalaldehyde 2-Arylhydrazones and of Ethyl 2-Arylhydrazono-3-oxopropionates" (PDF), Z. Naturforsch., vol. 62b, pp. 529–536