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M1407

Sigma-Aldrich

Malononitrile

≥99%

Sinônimo(s):

Dicyanomethane

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About This Item

Fórmula linear:
CH2(CN)2
Número CAS:
109-77-3
Peso molecular:
66.06
Beilstein:
773697
Número CE:
203-703-2
Número MDL:
MFCD00001883
Código UNSPSC:
12352100
ID de substância PubChem:
24896644
NACRES:
NA.22

Nível de qualidade

200

Ensaio

≥99%

pb

220 °C (lit.)

pf

30-32 °C (lit.)

densidade

1.049 g/mL at 25 °C (lit.)

temperatura de armazenamento

2-8°C

cadeia de caracteres SMILES

N#CCC#N

InChI

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

chave InChI

CUONGYYJJVDODC-UHFFFAOYSA-N

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Descrição geral

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

Aplicação

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.

Embalagem

Packaged in glass bottles

Pictogramas

Skull and crossbonesEnvironment
GHS06,GHS09

Palavra indicadora

Danger

Classificações de perigo

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

Código de classe de armazenamento

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

Classe de risco de água (WGK)

WGK 3

Ponto de fulgor (°F)

186.8 °F - closed cup

Ponto de fulgor (°C)

86 °C - closed cup

Equipamento de proteção individual

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

Escolha uma das versões mais recentes:

Certificados de análise (COA)

Lot/Batch Number
BCCC0575
BCCC0574
BCBZ6382
MKCG7245
BCBV1735

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1,5-Dicyanopentane 98%

Sigma-Aldrich

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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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