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Merck

690414

Malononitrile

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

Synonym(s):

Dicyanomethane

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About This Item

Linear Formula:
CH2(CN)2
CAS Number:
109-77-3
Molecular Weight:
66.06
UNSPSC Code:
12352100
NACRES:
NA.22
PubChem Substance ID:
329761337
EC Number:
203-703-2
Beilstein/REAXYS Number:
773697
MDL number:
MFCD00001883

Key Documents

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Product Name

Malononitrile, Arxada quality, ≥99.0% (calculated, GC, KF)

InChI

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

SMILES string

N#CCC#N

InChI key

CUONGYYJJVDODC-UHFFFAOYSA-N

assay

≥99.0% (calculated, GC, KF)

form

liquid

quality

Arxada quality

manufacturer/tradename

Arxada AG

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.)

functional group

nitrile

storage temp.

2-8°C

Quality Level

100

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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.

pictograms

Skull and crossbonesEnvironment
GHS06,GHS09

signalword

Danger

Hazard Classifications

Acute Tox. 2 Oral - Acute Tox. 3 Dermal - Acute Tox. 3 Inhalation - Aquatic Acute 1 - Aquatic Chronic 1 - Eye Irrit. 2 - Skin Sens. 1

Storage Class

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

ppe

dust mask type N95 (US), Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges

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Certificates of Analysis (COA)

Lot/Batch Number
BCCH5437
BCCC0574
BCCC0575
BCBZ6382
BCBS5662V

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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)
Malononitrile.
e-EROS Encyclopedia of Reagents for Organic Synthesis. (2001)
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 condensation of salicylaldehydes and malononitrile revisited: synthesis of new dimeric chromene derivatives.
Costa, Marta et al.
The Journal of Organic Chemistry, 73(5), 1954-1962 (2008)
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