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28321-79-1

28321-79-1 Structure

28321-79-1 Structure
IdentificationBack Directory
[Name]

diiminosuccinonitrile
[CAS]

28321-79-1
[Synonyms]

DISN
diiminosuccinonitrile
Diiminobutanedinitrile
2,3-Diiminosuccinonitrile
2,3-Diiminobutanedinitrile
2,3-Bisiminobutanedinitrile
Butanedinitrile, 2,3-diimino-
ETHANEDICARBONIMIDOYL DICYANIDE
ETHANEDICARBONIMIDOYL DICYANIDE(WXG02347)
[EINECS(EC#)]

248-963-8
[Molecular Formula]

C4H2N4
[MDL Number]

MFCD13182388
[MOL File]

28321-79-1.mol
[Molecular Weight]

106.09
Chemical PropertiesBack Directory
[Melting point ]

165-166 °C
[Boiling point ]

142.2±23.0 °C(Predicted)
[density ]

1.26±0.1 g/cm3(Predicted)
[solubility ]

acetone (21), THF (21), MeCN (18), DMAc (5.9), ether (1.5); insol benzene and hydrocarbons.
[pka]

-3.46±0.70(Predicted)
Hazard InformationBack Directory
[Uses]

Diiminosuccinonitrile reacts with electron-rich alkenes to form dicyanotetrahydropyrazines; it reacts with ketones to form dicyanoisoimidazoles.
[Preparation]

A solution of dry Triethylamine (1.5 mL) in CH2Cl2 (15 mL) is added dropwise over  45 min to a solution of Hydrogen Cyanide (20 g, 0.74 mol) and cyanogen (17.4 g, 0.34 mol) in CH2Cl2 (120 mL) at -45 to -40 °C; the reaction is mildly exothermic and DISN precipitates as the triethylamine is  added; after 30 min the product is collected while still cold and washed with CH2Cl2 and ether to give 33.6  g (95%) of DISN as a fine tan powder of sufficient purity for synthetic use.
[Synthesis Reference(s)]

The Journal of Organic Chemistry, 37, p. 4133, 1972 DOI: 10.1021/jo00798a037
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