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Sigma-Aldrich

Benzylidenemalononitrile

98%

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About This Item

Linear Formula:
C6H5CH=C(CN)2
CAS Number:
2700-22-3
Molecular Weight:
154.17
EC Number:
220-283-6
MDL number:
MFCD00001855
UNSPSC Code:
12352100
PubChem Substance ID:
24848816

assay

98%

mp

83-85 °C (lit.)

SMILES string

N#C\C(=C/c1ccccc1)C#N

InChI

1S/C10H6N2/c11-7-10(8-12)6-9-4-2-1-3-5-9/h1-6H

InChI key

WAVNYPVYNSIHNC-UHFFFAOYSA-N

Related Categories

General description

Benzylidenemalononitrile undergoes rapid and catalyst-free solid/vapor reaction with primary alkyl amines to yield N-benzylidene-amine. It undergoes addition reaction with octyl- and decylzirconocene chloride. It is a potential substrate for soluble methane monooxygenase.

Application

Benzylidenemalononitrile was used in fluorescence-based assay for determination of soluble methane monooxygenase activity in solution.

pictograms

Exclamation mark
GHS07

signalword

Warning

Hazard Classifications

Acute Tox. 4 Dermal - Acute Tox. 4 Inhalation - Acute Tox. 4 Oral - Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

target_organs

Respiratory system

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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A R Miller et al.
Applied microbiology and biotechnology, 58(2), 183-188 (2002-03-06)
A fluorescence-based assay was developed to estimate soluble methane monooxygenase (sMMO) activity in solution. Whole cells of Methylosinus trichosporium OB3b expressing sMMO were used to oxidize various compounds to screen for fluorescent products. Of the 12 compounds tested, only coumarin
Liqi Shi et al.
Chemical communications (Cambridge, England), 50(7), 872-874 (2013-12-04)
A new rapid and catalyst-free solid/vapor reaction between benzylidenemalonate/benzylidenemalononitrile and primary alkyl amines was found. With these as sensory units of fluorescent polymers, probes for primary amine vapor with high sensitivity and selectivity were developed.
Yuanhong Liu et al.
The Journal of organic chemistry, 67(20), 7019-7028 (2002-10-02)
Direct addition of alkylzirconocenes to activated alkenes was found, for the first time. Octyl- and decylzirconocene chloride reacted with benzylidenemalononitrile to give the corresponding addition products after hydrolysis in 86% and 79% yield, respectively. Zirconacyclopentanes showed a similar reactivity toward

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