19005-04-0

Basic information

• Product Name: bicyclo[2.2.2]octa-2,5-diene-2,3-dicarbonitrile
• Synonyms: 2,3-Dicyanobicyclo(2.2.2)octa-2,5-diene; 2,3-Dicyanobicyclo[2.2.2]octa-2,5-diene
• CAS NO: 19005-04-0
• Molecular Formula: C₁₀H₈N₂
• Molecular Weight: 156.1839
• Mol File: 19005-04-0.mol

Chemical Properties

• Melting Point: 105 °C(Solv: methanol (67-56-1))
• Boiling Point: 307.7°C at 760 mmHg
• Flash Point: 147.8°C
• Density: 1.18g/cm³
• Vapor Pressure: 0.000714mmHg at 25°C
• Refractive Index: 1.574
• CAS DataBase Reference: bicyclo[2.2.2]octa-2,5-diene-2,3-dicarbonitrile(CAS DataBase Reference)
• NIST Chemistry Reference: bicyclo[2.2.2]octa-2,5-diene-2,3-dicarbonitrile(19005-04-0)
• EPA Substance Registry System: bicyclo[2.2.2]octa-2,5-diene-2,3-dicarbonitrile(19005-04-0)

Safety Data

• Hazardous Substances Data: 19005-04-0(Hazardous Substances Data)

Upstream product

• 1165952-91-9 cyclohexa-1,3-diene 
• 825-24-1 bicyclo<2.2.1>hepta-2,5-diene-2,3-dicarbonitrile 
• 1071-98-3 2-butynedinitrile 

Downstream Products

• 7399-31-7 2,3-Dicyan-bicyclo<2.2.2>octen-(2) 

Relevant articles and documents

1-Bromo-1,2-dicyanoethylene: A dicyanoacetylene synthon useful in tetraazaporphyrin synthesis

Dicyanoacetylene, a highly reactive dienophile, readily reacts to form substituted maleonitriles which serve as precursors to soluble tetraazaporphyrins. Unfortunately, dicyanoacetylene is difficult to synthesize in large quantities. We report here a new dicyanoacetylene synthon, 1-bromo-1,2-dicyanoethylene, which is easily made in high yield by reaction of elemental bromine with fumaronitrile and easily purified by vacuum distillation. The resulting 5:1 mixture of geometric isomers reacts with dienes via a Diels-Alder reaction followed by elimination of HBr to give substituted maleonitriles. We demonstrate the utility of these reactions by reporting the synthesis of a novel, soluble tetraazaporphyrin bearing four 1,4-fused cyclohexyl groups on the macrocycle periphery.

Synthesis of phthalocyanine fused with bicyclo[2.2.2]octadienes and thermal conversion into naphthalocyanine

Mg complex of phthalocyanine fused with bicyclo[2.2.2]octadiene (BCOD) units is prepared by the reaction of BCOD-fused phthalonitrile with Mg(OPr)2 in PrOH at 100 °C overnight in 42% yield. Subsequent heating the product at 250 °C results in clean formation naphthalocyanine via the retro Diels-Alder reaction. An attempt to the synthesis of BCOD-fused tetraazaporphyrin by the similar cyclization of the Diels-Alder adduct of dicyanoacetylene with 1,3-cyclohexadiene was unsuccessful.

SYNTHESIS OF anti-SESQUINORBORNENE AND RELATED POLYCYCLIC ALKENES via REDUCTIVE ELIMINATION OF VICINAL DICYANO DERIVATIVES

A methodology for the preparation of both endocyclic unsaturated molecules via reductive elimination of vicinal dicyano derivatives is reported.The method is useful for the preparation of anti-sesquinorbornene and related hitherto unknown molecules starting from the respective vicinal dicyano derivatives which are readily available via Diels-Alder reactions.From a practical point of view, the best decyanation procedure for these substrates is to use finely dispersed sodium in tetrahydrofuran under sonication.The X-ray analysis of anti-1,4,4a,5,8,8a-hexahydro-1,4;5,8-dimethanonaphthalene-4a,8a-dicarbonitrile, 3, is reported.Crystal data: orthorhombic, space group P212121; Z=4; a=16.059(5), b=8.920(3), c=7.592(3) Angstroem; V=1087.5 Angstroem3, Dc=1.27 g*cm-3.