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M1407

Sigma-Aldrich

Malononitrile

≥99%

Sinonimo/i:

Dicyanomethane

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About This Item

Formula condensata:
CH2(CN)2
Numero CAS:
109-77-3
Peso molecolare:
66.06
Beilstein:
773697
Numero CE:
203-703-2
Numero MDL:
MFCD00001883
Codice UNSPSC:
12352100
ID PubChem:
24896644
NACRES:
NA.22

Saggio

≥99%

P. ebollizione

220 °C (lit.)

Punto di fusione

30-32 °C (lit.)

Densità

1.049 g/mL at 25 °C (lit.)

Temperatura di conservazione

2-8°C

Stringa SMILE

N#CCC#N

InChI

1S/C3H2N2/c4-2-1-3-5/h1H2
CUONGYYJJVDODC-UHFFFAOYSA-N

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Categorie correlate

Descrizione generale

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

Applicazioni

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.

Confezionamento

Packaged in glass bottles

Pittogrammi

Skull and crossbonesEnvironment
GHS06,GHS09

Avvertenze

Danger

Indicazioni di pericolo

H300,H311 + H331,H317,H319,H410

Classi di pericolo

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

Codice della classe di stoccaggio

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

Classe di pericolosità dell'acqua (WGK)

WGK 3

Punto d’infiammabilità (°F)

186.8 °F - closed cup

Punto d’infiammabilità (°C)

86 °C - closed cup

Dispositivi di protezione individuale

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

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Certificati d'analisi (COA)

Lot/Batch Number
BCCC0575
BCCC0574
BCBZ6382
BCBV1735
BCBS5662V

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1,5-Dicyanopentane 98%

Sigma-Aldrich

D79004

1,5-Dicyanopentane

4-Phenoxybenzoic acid 97%

Sigma-Aldrich

246182

4-Phenoxybenzoic acid

Methyl cyanoacetate 99%

Sigma-Aldrich

108421

Methyl cyanoacetate

2-[Bis(methylthio)methylene]malononitrile 97%

Sigma-Aldrich

766534

2-[Bis(methylthio)methylene]malononitrile

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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