2008/03/14 by Vasu Nair, Crystal L. O'Neil, Peng George Wang · 2 citations
Chemistry · #Analytical Chemistry and Chromatography #Oxidative Organic Chemistry Reactions #Mass Spectrometry Techniques and Applications
paper · doi:10.1002/047084289x.rm013.pub2
openalex publication_date 2008/03/14 · openalex created_date 2022/05/12 · openalex updated_date 2026/07/29
[542-78-9] C3H4O2 (MW 72.07) InChI = 1S/C3H4O2/c4-2-1-3-5/h2-3H,1H2 InChIKey = WSMYVTOQOOLQHP-UHFFFAOYSA-N (behaves as multifunctional compound;1 aldehyde reactions;2-4 forms both cyclic and acyclic acetals;5 may react as vinylog of formic acid;6-8 chelates with metal ions as β-dialdehyde;8 behaves as push–pull alkene9) Alternate Names: MDA; malonaldehyde; 1,3-propanedial. Physical Data: free aldehyde: hygroscopic needles; mp 72–74 °C; sodium salt: mp 245 °C (dec); UV λmax (0.1 N HCl) 245 nm (ɛ 12 800), (0.1 N NaOH) 267 nm (ɛ 29 400); 1H NMR (D2O) δ 5.73 (t, 1H, J = 10.1 Hz), 9.08 (d, 2H, J = 10.1 Hz); 13C NMR (D2O) δ 110.3, 193.6; pKa (H2O) = 4.5.1 Solubility: sodium salt: sol EtOH, MeOH, H2O; moderately sol CH2Cl2; insol ether. Form Supplied in: can be generated in situ from commercially available malondialdehyde bis(dimethyl acetal) [102-52-3] or bis(diethyl acetal) [122-31-6]. However, it is unstable and is best handled as its sodium salt. Handling, Storage, and Precautions: unstable and easily polymerizes. The generation of MDA in situ from the hydrolysis of its bis-acetals results in the formation of a number of side products, including β-alkoxyacrolein, 3,3-dialkoxypropionaldehyde, and fluorescent condensation polymers of MDA. Crystalline sodium MDA, which is much more stable than MDA, is the recommended synthetic reagent. Sodium MDA, if stored under nitrogen in a refrigerator, is stable for months.