Crosslinking agent for modification of proteins via amidationMalononitrile is used as a precursor in the preparation of anti-cancer drug, triamterene, adenine, methotrexate, thiamine, acrylic fibers and dyes. It is used in Knoevenagel condensation to prepare 2-chlorobenzalmalononitrile by reacting with 2-chlorobenzaldehyde. It acts as a leaching agent for gold. It is used as a raw material for the Gewald reaction of ketone or aldehyde to produce 2-aminothiophene using elemental sulfur and a base. Further, it plays an important role in the preparation of [1,6]-naphthyridines, gamma-ketoamides, 1,4-dihydropyridine, chromeno[2,3-b]pyridine and dihydro-1,4-dithiepine frameworks.
The Na derivative can be arylated by reaction with aryl halides with a Pd catalyst: J. Chem. Soc., Chem. Commun., 932 (1984). In the presence of butadiene, an additional 4-carbon unit is introduced: J. Chem. Soc., Perkin 1, 647 (1990):
Ternary condensation with an aromatic aldehyde and a cycloalkanone in the presence of ammonium acetate can give a variety of products. With cyclohexanone, the 2-amino-4-aryl-5,6,7,8-tetrahydroquinoline-3-carbonitriles are the major products: J. Chem. Res. (Synop.), 146 (1995).
Reviews of the chemistry of malononitrile: Chem. Rev., 69, 591 (1969); Synthesis, 165, 241 (1978); 925 (1981); Synlett, 2247 (2004).
Caruana, L.; Mondatori, M.; Corti, V.; Morales, S.; Mazzanti, A.; Fochi, M.; Bernardi, L. Catalytic Asymmetric Addition of Meldrums Acid, Malononitrile, and 1,3-Dicarbonyls to ortho-Quinone Methides Generated In Situ Under Basic Conditions. Chem. Eur. J. 2015, 21 (16), 6037-6041.
Adili, A.; Tao, Z. L.; Chen, D. F.; Han, Z. Y. Quinine-catalyzed highly enantioselective cycloannulation of o-quinone methides with malononitrile. Org. Biomol. Chem. 2015, 13 (8), 2247-2250.
Hazard Statements: H301-H311-H331
Toxic if swallowed. Toxic in contact with skin. Toxic if inhaled.
Precautionary Statements: P261-P280h-P301+P310a-P304+P340-P405-P501a
Avoid breathing dust/fume/gas/mist/vapours/spray. Wear protective gloves/clothing. IF SWALLOWED: IF INHALED: Remove to fresh air and keep at rest in a position comfortable for breathing. Store locked up. Dispose of contents/container in accordance with local/regional/national/international regulations.