Malononitrile

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Malononitrile
Skeletal formula of 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
3D model (JSmol)
773697
ChEBI
ChemSpider
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EC Number
  • 203-703-2
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1303
MeSH dicyanmethane
RTECS number
  • OO3150000
UNII
UN number 2647
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  • InChI=1S/C3H2N2/c4-2-1-3-5/h1H2 checkY
    Key: CUONGYYJJVDODC-UHFFFAOYSA-N checkY
  • N#CCC#N
Properties
CH2(CN)2
Molar mass 66.063 g·mol−1
Appearance Colourless or white solid[1]
Odor Sweet [3]
Density 1.049 g/cm3
Melting point 30–32 °C (86–90 °F; 303–305 K)[3]
Boiling point 220 °C (428 °F; 493 K)[3]
133 g/L (20 °C (68 °F; 293 K))[3]
Thermochemistry[citation needed]
110.29 J⋅K−1⋅mol-1
130.96 J⋅K−1⋅mol-1
187.7 to 188.1 kJ⋅mol−1
−1654.0 to −1654.4 kJ⋅mol−1
Hazards
GHS labelling:[3]
GHS06: ToxicGHS07: Exclamation markGHS09: Environmental hazard
Danger
H300, H311+H331, H317, H319, H410
P261, P264, P270, P271, P272, P273, P280, P301+P310+P330, P302+P352+P312, P304+P340+P311, P305+P351+P338, P333+P313, P337+P313, P362, P391, P403+P233, P405, P501
NFPA 704 (fire diamond)
[4]
NFPA 704 four-colored diamondHealth 4: Very short exposure could cause death or major residual injury. E.g. VX gasFlammability 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g. canola oilInstability 1: Normally stable, but can become unstable at elevated temperatures and pressures. E.g. calciumSpecial hazards (white): no code
4
1
1
Flash point 86 °C (187 °F; 359 K)
365 °C (689 °F; 638 K)[3]
Lethal dose or concentration (LD, LC):
  • 19 mg/kg (oral, mouse)
  • 14 mg/kg (oral, rat)[3]
  • 350 mg/kg (dermal, rat)
0.51 mg/L (inhalation, dust/mist, 4h)[3]
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
 Malonic acid
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

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

[edit | edit source]

It can be prepared by dehydration of cyanoacetamide.[5] Most commonly malononitrile is produced by the gas-phase reaction of acetonitrile and cyanogen chloride:[6]

NCCl + CH3CN → NCCH2CN + HCl

About 20,000,000 kilograms (20,000 LT) 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.[6]

Malononitrile is relatively acidic, with a pKa of 11 in water.[7] This allows it to be used in the Knoevenagel condensation, for example in the preparation of CS gas:

CS-chemical-synthesis
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.[8]

Interstellar occurrence

[edit | edit source]

Due to its permanent dipole moment (i.e., 3.735 ± 0.017 D),[9] 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.[10][11]

References

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