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Malononitrile

Organic compound with formula CH2(CN)2

Malononitrile

Organic compound with formula CH2(CN)2

|Malonodinitrile |Cyanoacetonitrile |Dicyanomethane |Malonic dinitrile |NFPA-H = 4 |NFPA-F = 1 |NFPA-R = 1 |NFPA-S = | (oral, mouse) | (oral, rat) | (dermal, rat) |Acetonitrile |Aminoacetonitrile |Glycolonitrile |Cyanogen |Propanenitrile |Aminopropionitrile |Pivalonitrile |Acetone cyanohydrin |Butyronitrile |Succinonitrile |Tetramethylsuccinonitrile

Malononitrile is an organic compound nitrile with the formula . It is a colorless or white solid, although aged samples appear yellow or even brown. It is a widely used building block in organic synthesis.

Preparation and reactions

It can be prepared by dehydration of cyanoacetamide. Most commonly malononitrile is produced by the gas-phase reaction of acetonitrile and cyanogen chloride: :

About 20000000 kg are produced annually (2007). Important outlets include the synthesis of thiamine, the drug triamterene and minoxidil, and the dyes disperse Yellow 90 and disperse Blue 354.

Malononitrile is relatively acidic, with a pKa of 11 in water. This allows it to be used in the Knoevenagel condensation, for example in the preparation of CS gas:

CS-chemical-synthesis

Despite its relative obscurity, Malononitrile is very useful in several reactions, the prime example being a suitable starting reagent for the Gewald reaction, where the nitrile condenses with a ketone or aldehyde in the presence of elemental sulfur and a base to produce a 2-aminothiophene. It can also be used as a Michael donor.

Interstellar occurrence

Due to its permanent dipole moment (i.e., 3.735 ± 0.017 D), malononitrile was detected in spectral emissions coming from interstellar cloud TMC-1 through the QUIJOTE line survey conducted with the Yebes 40 m radio telescope.

References

References

  1. [[International Union of Pure and Applied Chemistry]]. (2014). "Nomenclature of Organic Chemistry: IUPAC Recommendations and Preferred Names 2013". [[Royal Society of Chemistry.
  2. {{PGCH. 0378
  3. (3 January 2025). "Safety Data Sheet: Malononitrile". Sigma-Aldrich.
  4. (31 January 2025). "Safety Data Sheet: Malononitrile". ThermoFisher Scientific.
  5. (1945). "Malononitrile".
  6. "Malonic Acid and Derivatives".
  7. (11 April 2005). "pKa's of Inorganic and Oxo-Acids - Chem 206". Evans.
  8. Sabnis, R. W.. (1999). "2-Aminothiophenes By The Gewald Reaction". Journal of Heterocyclic Chemistry.
  9. "Michael Addition".
  10. (1960-02-01). "Microwave Spectrum of Malononitrile, CH2(CN)2. I. The Molecular Structure in the Ground Vibrational State". Bulletin of the Chemical Society of Japan.
  11. (August 2, 2024). "The rich interstellar reservoir of dinitriles: Detection of malononitrile and maleonitrile in TMC-1". Astronomy & Astrophysics.
  12. (2024-11-12). "Scientists found 'nitriles' in an interstellar cloud — here's why that could be huge".
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