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Malonic acid is acts as a building block in organic synthesis. It is also useful as a precursor for polyesters and alkyd resins, which is used in coating applications, thereby protecting against UV light, corrosion and oxidation. It acts as a cross linker in the coating industry and surgical adhesive. It finds application in the production of specialty chemicals, flavors and fragrances, polymer cross linkers and pharmaceuticals.
Knoevenagel condensation with aldehydes yields substituted acrylic (e.g. cinnamic) acids; review: Org. React., 15, 204 (1967). For an example of the Doebner modification, using pyridine as solvent/base, see: Org. Synth. Coll., 3, 425 (1955); a catalytic amount of piperidine often gives superior results; see, e.g.: Org. Synth. Coll., 4, 327 (1963).
Bew, S. P.; Stephenson, R.; Rouden, J.; Ashford, P. A.; Bourane, M.; Charvet, A.; Dalstein, V. M. D.; Jauseau, R.; Gipson, G. D. H.; Lozano, L. A. M. Bioinspired, Base- and Metal-Free, Mild Decarboxylative Aldol Activation of Malonic Acid Half Thioesters Under Phase-Transfer Reaction Conditions. Adv. Synth. Catal. 2015, 357 (6), 1245-1257.
Nakamura, S.; Sano, M.; Toda, A.; Nakane, D.; Masuda, H. Organocatalytic Enantioselective Decarboxylative Reaction of Malonic Acid Half Thioesters with Cyclic N-Sulfonyl Ketimines by Using N-Heteroarenesulfonyl Cinchona Alkaloid Amides. Chem. Eur. J. 2015, 21 (10), 3929-3932.
Hazard Statements: H302-H315-H318-H332-H335
Harmful if swallowed. Causes skin irritation. Causes serious eye damage. Harmful if inhaled. May cause respiratory irritation.
Precautionary Statements: P261-P264b-P270-P271-P280-P301+P312-P302+P352-P304+P340-P305+P351+P338-P310-P312-P330-P332+P313-P362-P501c
Avoid breathing dust/fume/gas/mist/vapours/spray. Wash face, hands and any exposed skin thoroughly after handling Do not eat, drink or smoke when using this product. Use only outdoors or in a well-ventilated area. Wear protective gloves/protective clothing/eye protection/face protection. IF SWALLOWED: Call a POISON CENTER or doctor/physician if you feel unwell. IF ON SKIN: Wash with plenty of soap and water. IF INHALED: Remove to fresh air and keep at rest in a position comfortable for breathing. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. Immediately call a POISON CENTER or doctor/physician. Rinse mouth. If skin irritation occurs: Get medical advice/attention. Take off contaminated clothing and wash before reuse. Dispose of contents/ container to an approved waste disposal plant