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1,5-Diazabicyclo[4.3.0]non-5-ene is employed for dehydrohalogenation reactions and base-catalyzed rearrangements in organic synthesis. It is an amidine base used in organic synthesis. Further, it is used as a resin curing agent and polyurethane catalyst.
The bicyclic amidines, DBN and DBU are strong organic bases initially introduced as reagents for dehydrohalogenation in vitamin A synthesis: Chem. Ber., 99, 2012 (1966).
For use of DBN in the aldol condensation, see: J. Am. Chem. Soc., 90, 3245 (1968). For esterification of thermally unstable carboxylic acids with diethyl sulfate at ambient temperature, see: Synth. Commun., 6, 89 (1976). For use in the alkylation of thiols with dihalomethanes, see: Synthesis, 952 (1980). In refluxing xylene, DBN and DBU cleave hindered esters, e.g. mesitoates, by alkyl-oxygen cleavage: Tetrahedron Lett., 3987 (1972); J. Org. Chem., 38, 1223 (1973).
Parviainen, A.; Wahlström, R.; Liimatainen, U.; Liitiä, T.; Rovio, S.; Helminen, J. K. J.; Hyväkkö, U.; King, A. W. T.; Suurnäkki, A.; Kilpeläinen, I. Sustainability of cellulose dissolution and regeneration in 1,5-diazabicyclo[4.3.0]non-5-enium acetate: a batch simulation of the IONCELL-F process. RSC Adv. 2015, 5 (85), 69728-69737.
Barykina-Tassa, O. V.; Snider, B. B. Studies toward the synthesis of cinachyramine. An efficient route to 1,5-diazabicyclo[4.4.0]dec-5-enes. Tetrahedron Lett. 2015, 56 (23), 3151-3154.
Hazard Statements: H314
Causes severe skin burns and eye damage.
Precautionary Statements: P260-P264b-P280-P301+P330+P331-P303+P361+P353-P304+P340-P305+P351+P338-P310-P363-P501c
Do not breathe dust/fume/gas/mist/vapours/spray. Wash face, hands and any exposed skin thoroughly after handling Wear protective gloves/protective clothing/eye protection/face protection. IF SWALLOWED: Rinse mouth. Do NOT induce vomiting. IF ON SKIN (or hair): Remove/Take off immediately all contaminated clothing. Rinse skin with water/shower. IF INHALED: Remove to fresh air and keep at rest in a position comfortable for breathing. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. Immediately call a POISON CENTER or doctor/physician. Wash contaminated clothing before reuse. Dispose of contents/ container to an approved waste disposal plant