1,8-Diazabicyclo[5.4.0]undec-7-ene: a useful organic reagent

Introduction

1,8-Diazabicyclo[5.4.0]undec-7-ene, also known as DBU or Diazabicycloundecene, is used as a complexing ligand, a catalyst, and a non-nucleophilic base in organic synthesis. It is readily sol water, ethanol, benzene, acetone, ethyl acetate, carbon tetrachloride, diethyl ether, dioxane, 1,4-butanediol, dimethyl sulfoxide, and hardly sol petroleum ether. It is a non-nucleophilic base generally used for dehydrohalogenation and has exhibited versatile reactivity[1].

Reaction profile

1,8-Diazabicyclo[5.4.0]undec-7-ene could be used in organic soluble base for elimination reactions, isomerizations, esterifications, amidations, etherifications, condensations, carboxylations/carbonylations, and halogenations[2].

Toxicity

Material is extremely destructive to tissue of the mucous membranes and upper respiratory tract, eyes, and skin. Cough, Shortness of breath, Headache, and Nausea may occur after exposure to this substance.

Storage

1,8-Diazabicyclo[5.4.0]undec-7-ene is stable at ambient temperatures but is hygroscopic; overexposure to the atmosphere results in water absorption which can lead to hydrolysis; rate of hydrolysis to N-(3-aminopropyl)-ε-caprolactam (10 wt% soln; molar ratio 1∶76) is 3 × 10−4 mol%−1 min−1; half-life for a 0.657 molar soln is 33 min at 35 °C; contact with undiluted product may cause skin irritation or burns.

References

[1] Ashok Kumar Morri, Venkata Ramana Doddi*, Yadagiri Thummala. “The Dual Role of 1,8-Diazabicyclo[5.4.0]undec-7-ene (DBU) in the Synthesis of Terminal Aryl- and Styryl-Acetylenes via Umpolung Reactivity.” Organic Letters 17 18 (2015): 4640–4643.

[2] Ashok Kumar Morri, Venkata Ramana Doddi, Yadagiri Thummala. “ChemInform Abstract: The Dual Role of 1,8-Diazabicyclo[5.4.0]undec-7-ene (DBU) in the Synthesis of Terminal Aryl- and Styryl-Acetylenes via Umpolung Reactivity.” ChemInform 47 6 (2016).

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