Malononitrile

Last updated
Malononitrile
Malondinitrile Structural Formula V1.svg
Ball-and-stick model Malononitrile-3D-balls.png
Ball-and-stick model
Space-filling model Malononitrile-3D-spacefill.png
Space-filling model
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 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 203-703-2
1303
MeSH dicyanmethane
PubChem CID
RTECS number
  • OO3150000
UNII
UN number 2647
  • InChI=1S/C3H2N2/c4-2-1-3-5/h1H2 X mark.svgN
    Key: CUONGYYJJVDODC-UHFFFAOYSA-N X mark.svgN
  • N#CCC#N
Properties
C3H2N2
Molar mass 66.063 g·mol−1
AppearanceColourless 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
Std molar
entropy (S⦵298)
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:
GHS-pictogram-skull.svg GHS-pictogram-pollu.svg
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).
X mark.svgN  verify  (what is  Yes check.svgYX mark.svgN ?)

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.

Contents

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-Gas-Synthese.svg
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]

See also

Related Research Articles

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Acetonitrile, often abbreviated MeCN, is the chemical compound with the formula CH3CN and structure H3C−C≡N. This colourless liquid is the simplest organic nitrile. It is produced mainly as a byproduct of acrylonitrile manufacture. It is used as a polar aprotic solvent in organic synthesis and in the purification of butadiene. The N≡C−C skeleton is linear with a short C≡N distance of 1.16 Å.

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Phenacyl chloride, also commonly known as chloroacetophenone, is a substituted acetophenone. It is a useful building block in organic chemistry. Apart from that, it has been historically used as a riot control agent, where it is designated CN. It should not be confused with cyanide, another agent used in chemical warfare, which has the chemical structure CN−.

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<span class="mw-page-title-main">Malonic acid</span> Carboxylic acid with chemical formula CH2(COOH)2

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Diazomethane is the chemical compound CH2N2, discovered by German chemist Hans von Pechmann in 1894. It is the simplest diazo compound. In the pure form at room temperature, it is an extremely sensitive explosive yellow gas; thus, it is almost universally used as a solution in diethyl ether. The compound is a popular methylating agent in the laboratory, but it is too hazardous to be employed on an industrial scale without special precautions. Use of diazomethane has been significantly reduced by the introduction of the safer and equivalent reagent trimethylsilyldiazomethane.

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<span class="mw-page-title-main">Cyanamide</span> Chemical compound featuring a nitrile group attached to an amino group

Cyanamide is an organic compound with the formula CN2H2. This white solid is widely used in agriculture and the production of pharmaceuticals and other organic compounds. It is also used as an alcohol-deterrent drug. The molecule features a nitrile group attached to an amino group. Derivatives of this compound are also referred to as cyanamides, the most common being calcium cyanamide (CaCN2).

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References

  1. 1 2 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. 1 2 3 4 5 6 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. 1 2 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.
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