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690414

Sigma-Aldrich

Malononitrile

Lonza quality, ≥99.0% (calculated, GC, KF)

Synonym(s):
Dicyanomethane
Linear Formula:
CH2(CN)2
CAS Number:
Molecular Weight:
66.06
Beilstein:
773697
EC Number:
MDL number:
PubChem Substance ID:

Quality Level

grade

Lonza quality

assay

≥99.0% (calculated, GC, KF)

manufacturer/tradename

Lonza Ltd

impurities

≤0.10% water
≤0.50% (E)-2-butenedinitrile
≤0.50% (Z)-2-butenedinitrile
≤0.50% butanedinitrile

bp

220 °C (lit.)

mp

30-32 °C (lit.)

density

1.049 g/mL at 25 °C (lit.)

storage temp.

2-8°C

SMILES string

N#CCC#N

InChI

1S/C3H2N2/c4-2-1-3-5/h1H2

Inchi Key

CUONGYYJJVDODC-UHFFFAOYSA-N

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Application

Malononitrile is an active methylene reagent useful for condensation reactions to synthesize various synthetic intermediates and heterocycles. It is extensively used in the Knoevenagel condensation with various aldehydes and ketones.
Some of the reactions where malononitrile is used as a reactant are:
  • Synthesis of 2-pyran-4-ylidene-malononitrile (PM) based red light emitting polymers.
  • Synthesis of polysubstituted dihydropyridines.
  • Synthesis of various chromene derivatives upon treating with salicylic aldehydes.
  • Synthesis of triselenium dicyanide by treating it with selenium dioxide.

Packaging

10 kg in composite drum
1 kg in glass bottle

Pictograms

Skull and crossbonesEnvironment

Signal Word

Danger

Hazard Statements

Hazard Classifications

Acute Tox. 3 Dermal - Acute Tox. 3 Inhalation - Acute Tox. 3 Oral - Aquatic Acute 1 - Aquatic Chronic 1

Storage Class Code

6.1A - Combustible, acute toxic Cat. 1 and 2 / very toxic hazardous materials

WGK

WGK 3

Flash Point(F)

186.8 °F - closed cup

Flash Point(C)

86 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US),Eyeshields,Gloves

Certificate of Analysis

Certificate of Origin

Malononitrile.
e-EROS Encyclopedia of Reagents for Organic Synthesis. (2001)
Synthesis of polysubstituted dihydropyridines by four-component reactions of aromatic aldehydes, malononitrile, arylamines, and acetylenedicarboxylate.
Sun, Jing et al.
Organic Letters, 12(16), 3678-3681 (2010)
Triselenium dicyanide from malononitrile and selenium dioxide. One-pot synthesis of selenocyanates.
Kachanov, Andrey V et al.
Tetrahedron Letters, 45(23), 4461-4463 (2004)
Synthesis and characterization of new red-emitting polyfluorene derivatives containing electron-deficient 2-pyran-4-ylidene- malononitrile moieties.
Peng, Qiang et al.
Macromolecules, 37(2), 260-266 (2004)
The Knoevenagel condensation reaction of aromatic aldehydes with malononitrile by grinding in the absence of solvents and catalysts.
Ren, Zhongjiao et al.
Synthetic Communications, 32(22), 3475-3479 (2002)

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