Malononitrile

Malononitrile is an organic compound nitrile with the formula CH2(CN)2. 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.

Malononitrile
Names
IUPAC name
Malononitrile[1]
Preferred IUPAC name
Propanedinitrile[1]
Other names
Malonodinitrile, Cyanoacetonitrile, Dicyanomethane, Malonic dinitrile[2]
Identifiers
3D model (JSmol)
773697
ChEBI
ChemSpider
ECHA InfoCard 100.003.368
EC Number
  • 203-703-2
1303
MeSH dicyanmethane
RTECS number
  • OO3150000
UNII
UN number 2647
  • InChI=1S/C3H2N2/c4-2-1-3-5/h1H2 N
    Key: CUONGYYJJVDODC-UHFFFAOYSA-N N
  • N#CCC#N
Properties
CH2(CN)2
Molar mass 66.063 g·mol−1
Appearance Colourless or white solid[2]
Density 1.049 g cm−3
Melting point 32 °C; 89 °F; 305 K
Boiling point 220.1 °C; 428.1 °F; 493.2 K
13% (20 °C)[2]
Thermochemistry
110.29 J K−1 mol−1
130.96 J K−1 mol−1
187.7 to 188.1 kJ mol−1
−1,654.0 to −1,654.4 kJ mol−1
Hazards
GHS labelling:
Danger
H301, H311, H331, H410
P261, P273, P280, P301+P310, P311
Flash point 86 °C (187 °F; 359 K)
Lethal dose or concentration (LD, LC):
  • 19 mg kg−1 (oral, mouse)
  • 350 mg kg−1 (dermal, rat)
NIOSH (US health exposure limits):
PEL (Permissible)
 none[2]
REL (Recommended)
 TWA 3 ppm (8 mg/m3)[2]
IDLH (Immediate danger)
 N.D.[2]
Related compounds
Related alkanenitriles
Related compounds
 DBNPA
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N verify (what is YN ?)
Infobox references

Preparation and reactions

It can be prepared by dehydration of cyanoacetamide.[3] This method is mainly practiced in China where environmental rules are lax. Most commonly malononitrile is produced by the gas-phase reaction of acetonitrile and cyanogen chloride:[4]

NCCl + CH3CN → NCCH2CN + HCl

About 20,000,000 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.[4]

Malononitrile is relatively acidic, with a pKa of 11 in water.[5] This allows it to be used in the Knoevenagel condensation, for example in the preparation of CS gas:

Malononitrile is a suitable starting material 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.[6]

Drugs List

Malononitrile is used in the synthesis of the following list of agents:

  1. AG 18
  2. AG-82
  3. AG-126
  4. AG-1024
  5. AG 1112 [153150-84-6][7]
  6. Amprolium
  7. Ampyrimine
  8. 3-AQC
  9. CCCP
  10. Diaveridine
  11. Enloplatin
  12. FCCP
  13. Furterene
  14. Ibrutinib
  15. LY290181
  16. Milrinone Malononitrile [140942-11-6]
  17. Olanzapine
  18. Ormetoprim
  19. Propyrisulfuron
  20. RBC8
  21. Simendan
  22. Triamterine
  23. Triap
  24. Trimethoprim
  25. UCPH 101

See also

References
  1. International Union of Pure and Applied Chemistry (2014). Nomenclature of Organic Chemistry: IUPAC Recommendations and Preferred Names 2013. The Royal Society of Chemistry. p. 902. doi:10.1039/9781849733069. ISBN 978-0-85404-182-4.
  2. NIOSH Pocket Guide to Chemical Hazards. "#0378". National Institute for Occupational Safety and Health (NIOSH).
  3. Surrey, Alexander (1945). "Malononitrile". Organic Syntheses. 25: 63–64. doi:10.15227/orgsyn.025.0063.
  4. Strittmatter, Harald; Hildbrand, Stefan; Pollak, Peter (2007). "Malonic Acid and Derivatives". Ullmann's Encyclopedia of Industrial Chemistry. doi:10.1002/14356007.a16_063.pub2. ISBN 978-3527306732.
  5. Evans pKa table
  6. Sabnis, R. W.; Rangnekar, D. W.; Sonawane, N. D. (1999). "2-Aminothiophenes By The Gewald Reaction". Journal of Heterocyclic Chemistry. 36 (2): 333–345. doi:10.1002/jhet.5570360203. Retrieved 2007-07-18.
  7. Dotsenko, V. V., Krivokolysko, S. G., Semenova, A. M. (November 2018). "Heterocyclization reactions using malononitrile dimer (2-aminopropene-1,1,3-tricarbonitrile)". Chemistry of Heterocyclic Compounds. 54 (11): 989–1019. doi:10.1007/s10593-018-2383-y. ISSN 0009-3122.
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