In the Mitsunobu reaction, a major drawback of this reaction is formation of two co-products, hydrazinedicarboxylate and phosphine oxide, which must be removed from the reaction mixture to isolate a target compound.
In case of using well known DEAD (diethyl azodicarboxylate) or DIAD (diisopropyl azodicarboxylate), separation of co-produced diethyl or diisopropyl hydrazinedicarboxylate often requires several process steps and large amounts of solvent for the purification because of the solubility and polarity of the hydrazine-dicarboxylates.
DMEAD® (di-2-methoxyethyl azodicarboxylate) is a new reagent for the Mitsunobu reaction developed by Prof. T. Sugimura (Graduate School of Material Science, University of Hyogo.).
The co-produced hydrazine (di-2-methoxyethyl hydrazinedicarboxylate) is highly water soluble (0.55 g/mL), and can be removed by washing with neutral water.
We assume that DMEAD® can contribute to establish an operationally easy, cost effective, and environmentally friendly process in the Mitsunobu reaction.

Reference: Chem. Lett. 2007, 36, 566.

General

●CAS Registry No.:940868-64-4.
●MW:234.21oC.

Physical Data

●Appearance:Light Yellow Prism.
●Melting Point:40-41oC.
●Decomposition Temp.:210oC,927 J/g(DSC).

Solubility

●Soluble in THF, Toluene, CH₂Cl₂,etc.

Special Feature

●The Rf value on TLC(Ethyl acetate/Hexane = 1/1) is 0.08.
●*Corresponding values of hydrazinedicarboxylate from DIAD and DEAD are 0.65 and 0.44.