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About This Item
Linear Formula:
CH2(CN)2
CAS Number:
Molecular Weight:
66.06
Beilstein:
773697
EC Number:
MDL number:
UNSPSC Code:
12352100
PubChem Substance ID:
NACRES:
NA.22
Recommended Products
Quality Level
Assay
≥99%
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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General description
Malononitrile, a weak cyanocarbon acid, is a versatile compound with exceptional reactivity. This crystalline aliphatic nitrile is used as a building block to synthesize heterocyclic compounds and polymers
Application
Malononitrile may be used in the:
- base-promoted on-water synthesis of [1,6]-naphthyridines.†
- synthesis of γ-ketoamides.
- preparation of heterocyclic privileged medicinal scaffolds involving pyridine, 1,4-dihydropyridine, chromeno[2,3-b]pyridine and dihydro-1,4-dithiepine frameworks.
Packaging
Packaged in glass bottles
Signal Word
Danger
Hazard Statements
Precautionary Statements
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 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
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High-Performance Quinoline-Malononitrile Core as a Building Block for the Diversity-Oriented Synthesis of AIEgens
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Angewandte Chemie (International Edition in English), 59, 9812-9825 (2020)
Enxiang Wei et al.
Organic & biomolecular chemistry, 12(33), 6389-6392 (2014-07-11)
An efficient synthesis of γ-ketoamides was developed by the one-pot multicomponent reaction of chalcones, malononitrile and DMF (as both the reactant and solvent) in the presence of NaOH (3.0 equiv.). The reaction features high atom economy, easily available starting materials
The chemistry of malononitrile.
F Freeman
Chemical reviews, 69(5), 591-624 (1969-10-01)
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Nature communications, 9(1), 2903-2903 (2018-07-27)
Electron transfer reactions are arguably the simplest chemical reactions but they have not yet ceased to intrigue chemists. Charge-separation and charge-recombination reactions are at the core of life-sustaining processes, molecular electronics and solar cells. Intramolecular electron donor-acceptor systems capture the
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Organic letters, 15(5), 1072-1075 (2013-02-21)
The Hg(II)-specific intramolecular cyclization reaction of ethynyl phenols was carried out for the first time in semiaqueous media at ambient temperature. The reaction unit (ethynyl phenol) was coupled with a malononitrile derivative (signal unit), which afforded the chromogenic Hg(II) indicator
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