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M1407

Sigma-Aldrich

Malononitrile

≥99%

Synonym(s):
Dicyanomethane
Linear Formula:
CH2(CN)2
CAS Number:
Molecular Weight:
66.06
Beilstein:
773697
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.22

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, widely used in condensation reactions.

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

5, 100, 500 g in glass bottle
Packaged in glass bottles

Pictograms

Skull and crossbonesEnvironment

Signal Word

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 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

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)
Bandita Datta et al.
Ultrasonics sonochemistry, 19(4), 725-728 (2012-02-14)
A one-pot three-component condensation of an aldehyde, malononitrile, and resorcinol has been achieved by ultrasound method. The reaction has been catalyzed by glycine in aqueous medium. This protocol afforded corresponding 2-amino-4H-chromenes in shorter reaction times, high yields and simple work-up...
Zhishan Su et al.
Organic & biomolecular chemistry, 9(18), 6402-6409 (2011-07-29)
The mechanism of Michael addition of malononitrile to chalcones catalyzed by Cinchona alkaloid aluminium(III) complex has been investigated by DFT and ONIOM methods. Calculations indicate that the reaction proceeds through a dual activation mechanism, in which Al(III) acts as a...
Tamer S Saleh et al.
Ultrasonics sonochemistry, 19(3), 491-497 (2011-11-29)
Novel fused pyrans were synthesized from the reaction of the tetrahydropyran-4-one with arylidine malononitriles. Different fused pyran derivatives were obtained from the mentioned reaction depending on type of catalyst used and type of energy used. Reactions were carried out under...

Articles

Knoevenagel Condensation Reaction

Knoevenagel Condensation is an organic reaction named after Emil Knoevenagel. It is a classic C-C bond formation reaction and a modification of the Aldol Condensation.

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