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Merck
CN

47980

Sigma-Aldrich

Fumaronitrile

purum, ≥98.0% (GC)

Synonym(s):

trans-1,2-Dicyanoethylene

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About This Item

Linear Formula:
NCCH=CHCN
CAS Number:
Molecular Weight:
78.07
Beilstein:
969245
EC Number:
MDL number:
UNSPSC Code:
12352100
PubChem Substance ID:
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grade

purum

Assay

≥98.0% (GC)

bp

186 °C (lit.)

mp

93-95 °C (lit.)

SMILES string

N#C\C=C\C#N

InChI

1S/C4H2N2/c5-3-1-2-4-6/h1-2H/b2-1+

InChI key

KYPOHTVBFVELTG-OWOJBTEDSA-N

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Other Notes

Precursor of the corresponding amidate, a cross-linking agent for modifying proteins via amidation according to Davies and Stark

Pictograms

Skull and crossbones

Signal Word

Danger

Hazard Statements

Precautionary Statements

Hazard Classifications

Acute Tox. 3 Oral

Storage Class Code

6.1D - Non-combustible acute toxic Cat.3 / toxic hazardous materials or hazardous materials causing chronic effects

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Information

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Certificates of Analysis (COA)

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Yinlong Yang et al.
Biomaterials, 33(31), 7803-7809 (2012-07-24)
We report a new strategy of using carrier-free pure near-infrared (NIR) dye nanoparticles (NPs) to achieve highly luminescent NIR fluorescent probes for in vitro and in vivo imaging. Bis(4-(N-(2-naphthyl)phenylamino) phenyl)-fumaronitrile (NPAPF) NPs are shown to exhibit favorable biocompatibility, wide-range pH
J M Wyatt et al.
Biodegradation, 6(2), 93-107 (1995-06-01)
Effluent from the manufacture of acrylonitrile is difficult to biodegrade. It contains nine major organic components: acetic acid, acrylonitrile, acrylamide, acrylic acid, acrolein, cyanopyridine, fumaronitrile, succinonitrile, and maleimide. A range of bacteria have been isolated that can grow on, or
R Schlegelmilch et al.
Journal of applied toxicology : JAT, 8(3), 201-209 (1988-06-01)
Two aliphatic nitriles, acetonitrile and fumaronitrile were tested for their genotoxic potential in three mutagenicity test systems: the Salmonella/microsome-assay, an assay using Saccharomyces cerevisiae (strain D7), and the bone marrow micronucleus test. Both compounds were tested with and without metabolic
Taegweon Lee et al.
Journal of the American Chemical Society, 131(5), 1692-1705 (2009-01-17)
A new series of heterocyclic oligomers based on the 1,3,4-oxadiazole ring were synthesized. Other electron-deficient cores (fluorenone and fumaronitrile) were introduced to investigate the oligomers as n-channel materials. The physical properties, thin film morphologies, and field-effect transistor characteristics of the
Wolfgang Knoll et al.
Organic letters, 12(10), 2366-2369 (2010-04-20)
Photolysis of aziadamantanes in the presence of fumaronitrile (FN) unexpectedly afforded conjugated 2H-azirines resulting from addition of the carbene to the CN triple bond. This represents the first example of a direct azirine formation starting from an alkylcarbene for which

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