Malononitrile

Organic compound with formula CH2(CN)2
Malononitrile
Skeletal formula of malononitrile
Ball-and-stick model
Ball-and-stick model
Space-filling model
Space-filling model
Names
IUPAC name
Malononitrile[2]
Preferred IUPAC name
Propanedinitrile[2]
Other names
Malonodinitrile, Cyanoacetonitrile, Dicyanomethane, Malonic dinitrile[1]
Identifiers
CAS Number
  • 109-77-3 checkY
3D model (JSmol)
  • Interactive image
Beilstein Reference
 773697
ChEBI
  • CHEBI:33186 ☒N
ChemSpider
  • 13884495 ☒N
ECHA InfoCard 100.003.368 Edit this at Wikidata
EC Number
  • 203-703-2
Gmelin Reference
 1303
MeSH dicyanmethane
PubChem CID
  • 8010
RTECS number
  • OO3150000
UNII
  • EBL1KKS93J checkY
UN number 2647
CompTox Dashboard (EPA)
  • DTXSID6021907 Edit this at Wikidata
InChI
  • InChI=1S/C3H2N2/c4-2-1-3-5/h1H2 ☒N
    Key: CUONGYYJJVDODC-UHFFFAOYSA-N ☒N
  • N#CCC#N
Properties
Chemical formula
 CH2(CN)2
Molar mass 66.063 g·mol−1
Appearance Colourless or white solid[1]
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)[1][clarification needed]
Thermochemistry
110.29 J K−1 mol−1
Std molar
entropy (S⦵298)
 130.96 J K−1 mol−1
Std enthalpy of
formation (ΔfH⦵298)
 187.7 to 188.1 kJ mol−1
Std enthalpy of
combustion (ΔcH⦵298)
 −1,654.0 to −1,654.4 kJ mol−1
Hazards
GHS labelling:
GHS06: Toxic GHS09: Environmental hazard
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[1]
REL (Recommended)
 TWA 3 ppm (8 mg/m3)[1]
IDLH (Immediate danger)
 N.D.[1]
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).
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Infobox references
Chemical compound

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.

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:

CS-chemical-synthesis
CS-chemical-synthesis

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. Amprolium
  6. Ampyrimine
  7. 3-AQC
  8. CCCP
  9. Diaveridine
  10. Enloplatin
  11. FCCP
  12. Furterene
  13. Ibrutinib
  14. LY290181
  15. Milrinone
  16. Olanzapine
  17. Ormetoprim
  18. Propyrisulfuron
  19. RBC8
  20. Simendan
  21. Triamterine
  22. Triap
  23. Trimethoprim
  24. UCPH 101

See also

References

  1. ^ a b c d e f NIOSH Pocket Guide to Chemical Hazards. "#0378". National Institute for Occupational Safety and Health (NIOSH).
  2. ^ a b 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.
  3. ^ Surrey, Alexander (1945). "Malononitrile". Organic Syntheses. 25: 63–64. doi:10.15227/orgsyn.025.0063.
  4. ^ a b 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.

External links

  • WebBook page for C3H2N2
  • CDC - NIOSH Pocket Guide to Chemical Hazards
Authority control databases: National Edit this at Wikidata
  • Germany