(2Z)-diaminobut-2-enedinitrile

• ChemBase ID: 287178
• Molecular Formular: C4H4N4
• Molecular Mass: 108.10136
• Monoisotopic Mass: 108.04359615
• SMILES: N#C/C(=C(/N)\C#N)/N
• Canonical SMILES: N#C/C(=C(\C#N)/N)/N
• InChI: InChI=1S/C4H4N4/c5-1-3(7)4(8)2-6/h7-8H2/b4-3-
• InChIKey: DPZSNGJNFHWQDC-ARJAWSKDSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2Z)-diaminobut-2-enedinitrile
• IUPAC Traditional name: (2Z)-diaminobut-2-enedinitrile
• Synonyms: 2,3-Diaminomaleonitrile; DAMN; Diaminomaleonitrile; 二氨基马来腈

Database IDs

• CAS Number: 1187-42-4
• EC Number: 214-697-6
• MDL Number: MFCD00001870
• Beilstein Number: 878333
• PubChem SID: 180672709
• PubChem CID: 2723951

CALCULATED PROPERTIES

• Acid pKa: 19.863813
• H Acceptors: 4
• H Donor: 2
• LogD (pH = 5.5): -1.9033605
• LogD (pH = 7.4): -1.9033605
• Log P: -1.9033605
• Molar Refractivity: 29.8154 cm^3
• Polarizability: 9.8784 Å^3
• Polar Surface Area: 99.62 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 178-182°C dec.
• Density: 1.360

Safety Information

• Storage Warning: Light Sensitive
• European Hazard Symbols: Toxic (T)
• UN Number: UN3439
• Hazard Class: 6.1
• Packing Group: III
• Risk Statements: 25-32
• Safety Statements: 7/9-36-45
• TSCA Listed: 是
• GHS Pictograms: GHS06
• GHS Hazard statements: H301
• GHS Precautionary statements: P264-P270-P301+P310-P321-P405-P501A

Product Information

• Purity: 98%

REFERENCES

• The tetramer of HCN. Useful precursor of various heterocycles, e.g. imidazoles: Synthesis, 767 (1988); J. Org. Chem., 39, 2341 (1974),pyrazines: J. Org. Chem., 39, 2341 (1974); 44, 827, 4871 (1979); J. Heterocycl. Chem., 11, 79 (1974); Heterocycles, 16, 1449 (1981), pteridines: J. Heterocycl. Chem., 23, 1299 (1986). For extension to synthesis of nucleosides, see: J. Org. Chem., 50, 747 (1985). For a review, with particular reference to its utility in heterocyclic synthesis, see: Tetrahedron, 59, 2749 (2003).