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Benzylidenemalononitrile

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Benzylidenemalononitrile Basic information
Product Name:Benzylidenemalononitrile
Synonyms:benzal-malonitril;benzylidene-malononitril;f2370;RARECHEM AL BX 0531;AKOS USSH-4110217;2-BENZYLIDENE-MALONONITRILE;tl237;beta,beta-styrenedicarbonitrile
CAS:2700-22-3
MF:C10H6N2
MW:154.17
EINECS:220-283-6
Product Categories:C10 to C27;Cyanides/Nitriles;Nitrogen Compounds;Building Blocks;C10 to C27;Chemical Synthesis;Nitrogen Compounds;Organic Building Blocks
Mol File:2700-22-3.mol
Benzylidenemalononitrile Structure
Benzylidenemalononitrile Chemical Properties
Melting point 83-85 °C (lit.)
Boiling point 120-125°C 0,6mm
density 1.1975 (rough estimate)
refractive index 1.4820 (estimate)
Fp 120-125°C/0.6mm
storage temp. Sealed in dry,Room Temperature
solubility soluble in Methanol
form powder to crystal
color White to Orange to Green
BRN 1907519
CAS DataBase Reference2700-22-3(CAS DataBase Reference)
Safety Information
Hazard Codes Xn
Risk Statements 20/21/22-36/37/38
Safety Statements 26-36/37/39
RIDADR 3276
WGK Germany 3
RTECS OO3500000
HazardClass 6.1
PackingGroup III
HS Code 29269095
MSDS Information
ProviderLanguage
ACROS English
SigmaAldrich English
ALFA English
Benzylidenemalononitrile Usage And Synthesis
Chemical PropertiesSLIGHTLY YELLOW NEEDLE-LIKE CRYSTALLINE POWDER
UsesBenzylidenemalononitrile was used in fluorescence-based assay for determination of soluble methane monooxygenase activity in solution.
Synthesis Reference(s)The Journal of Organic Chemistry, 49, p. 4819, 1984 DOI: 10.1021/jo00199a014
Tetrahedron Letters, 23, p. 4927, 1982 DOI: 10.1016/S0040-4039(00)85749-4
General DescriptionBenzylidenemalononitrile 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.
SynthesisBenzaldehyde (1.0eq) was put into a 250mL round-bottomed flask, distilled water (100mL) was added as solvent, put into a clean stirrer, and then malononitrile (1.2eq) was added, and the reaction was placed at room temperature for 12 h. After the reaction was finished by TLC, a large amount of solid was precipitated, and it was filtered, and the cake was washed with petroleum ether, and the white solid product, benzylidene malononitrile, was dried.
Purification MethodsRecrystallise the nitrile from EtOH [Bernasconi et al. J Am Chem Soc 107 3612 1985]. It has max at 307nm (EtOH). [Beilstein 9 H 895, 9 II 640, 9 III 4380, 9 IV 3462.]
Tag:Benzylidenemalononitrile(2700-22-3) Related Product Information
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