| Identification | Back 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 Properties | Back 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 Information | Back 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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