Abstract
[10140-89-3] C3H4Cl2O (MW 126.97) InChI = 1S/C3H4Cl2O/c4-1-3(5)2-6/h2-3H,1H2 InChIKey = IZRKUJREXIKAQM-UHFFFAOYSA-N (undergoes condensation reactions, ene reactions, 1,2-additions; α-chloro nitrone precursor) Alternate Name: 2,3-dichloropropanal. Physical Data: bp 45 °C/12 mmHg; nD20 1.4762; d20 1.3712 g cm−3. Solubility: sol most common organic solvents such as hexane, ether, THF, methylene chloride, ethanol, etc. Form Supplied in: colorless liquid; not commercially available. Analysis of Reagent Purity: NMR. Preparative Methods: the reagent is best prepared by bubbling an equimolar amount of dry Chlorine gas into neat Acrolein at 5 °C.2 The reaction temperature thereby rises spontaneously and is kept at 40 °C until the reaction has ended. Spinning band distillation at reduced pressure (12 mmHg) affords pure 2,3-dichloropropionaldehyde as a colorless liquid in 65% yield. Handling, Storage, and Precautions: as the reagent is prone to polymerization it should be used as prepared for best results. For a limited time it can be stored under nitrogen at 5 °C in tightly sealed bottles. Use in a fume hood.
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