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M1407

Sigma-Aldrich

Malononitrile

≥99%

Synonym(s):

Dicyanomethane

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About This Item

Linear Formula:
CH2(CN)2
CAS Number:
109-77-3
Molecular Weight:
66.06
Beilstein:
773697
EC Number:
203-703-2
MDL number:
MFCD00001883
UNSPSC Code:
12352100
PubChem Substance ID:
24896644
NACRES:
NA.22
Pricing and availability is not currently available.

Quality Level

200

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[1][2]

Application

Malononitrile may be used in the:
  • base-promoted on-water synthesis of [1,6]-naphthyridines.†
  • synthesis of γ-ketoamides.[3]
  • preparation of heterocyclic privileged medicinal scaffolds involving pyridine, 1,4-dihydropyridine, chromeno[2,3-b]pyridine and dihydro-1,4-dithiepine frameworks.[4]

Packaging

Packaged in glass bottles

Pictograms

Skull and crossbonesEnvironment
GHS06,GHS09

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

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Certificates of Analysis (COA)

Lot/Batch Number
BCCH5437
BCCC0575
BCCC0574
BCBZ6382
BCBV1735

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High-Performance Quinoline-Malononitrile Core as a Building Block for the Diversity-Oriented Synthesis of AIEgens
Z Guo, et al.
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)
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
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
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Questions

1–2 of 2 Questions  

  1. How can I determine the shelf life / expiration / retest date of this product?

    1 answer

    1. If this product has an expiration or retest date, it will be shown on the Certificate of Analysis (COA, CofA). If there is no retest or expiration date listed on the product's COA, we do not have suitable stability data to determine a shelf life. For these products, the only date on the COA will be the release date; a retest, expiration, or use-by-date will not be displayed.
      For all products, we recommend handling per defined conditions as printed in our product literature and website product descriptions. We recommend that products should be routinely inspected by customers to ensure they perform as expected.
      For products without retest or expiration dates, our standard warranty of 1 year from the date of shipment is applicable.
      For more information, please refer to the Product Dating Information document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/449/386/product-dating-information-mk.pdf

      Helpful?

  2. How is shipping temperature determined? And how is it related to the product storage temperature?

    1 answer

    1. Products may be shipped at a different temperature than the recommended long-term storage temperature. If the product quality is sensitive to short-term exposure to conditions other than the recommended long-term storage, it will be shipped on wet or dry-ice. If the product quality is NOT affected by short-term exposure to conditions other than the recommended long-term storage, it will be shipped at ambient temperature. As shipping routes are configured for minimum transit times, shipping at ambient temperature helps control shipping costs for our customers. For more information, please refer to the Storage and Transport Conditions document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/316/622/storage-transport-conditions-mk.pdf

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