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Thermo Scientific Chemicals
Malononitrile, 99%
CAS: 109-77-3 | C3H2N2 | 66.063 g/mol
化学物質識別子
CAS109-77-3
IUPAC Namepropanedinitrile
Molecular FormulaC3H2N2
InChI KeyCUONGYYJJVDODC-UHFFFAOYSA-N
SMILESN#CCC#N
さらに表示
仕様
スペックシート
スペックシートAppearance (Color)Colorless to white to pale cream to cream to yellow to orange to brown
FormCrystals or powder or crystalline powder or fused solid or clear liquid as melt
Assay (GC)≥98.5%
Identification (FTIR)Conforms
Melting Point (clear melt)29.0-35.0?C
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.
This Thermo Scientific Chemicals brand product was originally part of the Alfa Aesar product portfolio. Some documentation and label information may refer to the legacy brand. The original Alfa Aesar product / item code or SKU reference has not changed as a part of the brand transition to Thermo Scientific Chemicals.
Applications
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.
Solubility
Soluble in water, acetone, acetic acid, chloroform, ethanol, ether and benzene.
Notes
Store in a cool place. Incompatible with strong oxidizing agents, strong reducing agents, strong acids and strong bases.
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.
Solubility
Soluble in water, acetone, acetic acid, chloroform, ethanol, ether and benzene.
Notes
Store in a cool place. Incompatible with strong oxidizing agents, strong reducing agents, strong acids and strong bases.
RUO – Research Use Only
General References:
- 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 Meldrum’s 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.