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M1407

Sigma-Aldrich

Malonsäuredinitril

≥99%

Synonym(e):

Dicyanmethan

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About This Item

Lineare Formel:
CH2(CN)2
CAS-Nummer:
109-77-3
Molekulargewicht:
66.06
Beilstein:
773697
EG-Nummer:
203-703-2
MDL-Nummer:
MFCD00001883
UNSPSC-Code:
12352100
PubChem Substanz-ID:
24896644
NACRES:
NA.22

Assay

≥99%

bp

220 °C (lit.)

mp (Schmelzpunkt)

30-32 °C (lit.)

Dichte

1.049 g/mL at 25 °C (lit.)

Lagertemp.

2-8°C

SMILES String

N#CCC#N

InChI

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

InChIKey

CUONGYYJJVDODC-UHFFFAOYSA-N

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Allgemeine Beschreibung

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

Anwendung

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.

Verpackung

Packaged in glass bottles

Piktogramme

Skull and crossbonesEnvironment
GHS06,GHS09

Signalwort

Danger

Gefahreneinstufungen

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

Lagerklassenschlüssel

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

WGK

WGK 3

Flammpunkt (°F)

186.8 °F - closed cup

Flammpunkt (°C)

86 °C - closed cup

Persönliche Schutzausrüstung

Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges

Analysenzertifikate (COA)

Suchen Sie nach Analysenzertifikate (COA), indem Sie die Lot-/Chargennummer des Produkts eingeben. Lot- und Chargennummern sind auf dem Produktetikett hinter den Wörtern ‘Lot’ oder ‘Batch’ (Lot oder Charge) zu finden.

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The chemistry of malononitrile.
F Freeman
Chemical reviews, 69(5), 591-624 (1969-10-01)
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
Nikolai M Evdokimov et al.
The Journal of organic chemistry, 72(9), 3443-3453 (2007-04-06)
Heterocyclic privileged medicinal scaffolds involving pyridine, 1,4-dihydropyridine, chromeno[2,3-b]pyridine, and dihydro-1,4-dithiepine frameworks are prepared via a single-step multicomponent reaction of structurally diverse aldehydes with various thiols and malononitrile. Mechanistic studies of the synthetic pathway leading to pyridines reveal that 1,4-dihydropyridines undergo
Kamila K Mentel et al.
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
Ananta Kumar Atta et al.
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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