Diethyl azodicarboxylate

Clear orange to orange-red liquid

Reactant for preparation of:

• Immunostimulants α-Galactosylceramides
• Cellotriose and cellotetraose analogues as transition state mimics for mechanistic studies of cellulases
• Bisubstrate inhibitors with molecular recognition at the active site of catechol-O-methyltransferase
• Derivatives of F200 and S383 with cannabinoid CB1 receptor binding activities
• Aza-β-lactams via NHC-catalyzed [2 + 2] cycloaddition with ketenes

Reagent for:

• Annulation of N-protected imines
• α-thiocyanation of enolizable ketones with ammonium thiocyanate
• Diels-Alder reactions

A fluorescent CDK inhibitor for treatment of cancer

DOT Special Approval Submission is Under Review. Availability is Estimated as March 2012.

Diethyl azodicarboxylate (DEAD) can be obtained from 1,2-bis(ethoxycarbonyl)hydrazine by oxidation with nitric acid.

Dissolve DEAD in toluene, wash it with 10% NaHCO3 till neutral (may require several washes if too much hydrolysis had occurred: check IR for OH bands), then wash with H2O (2x), dry over Na2SO4, filter, evaporate the toluene and distil it through a short Vigreux column (p 11) at as high a vacuum as possible. The main portion boils at 107-111o/15mm. Since it is likely to explode, use an oil bath for heating the still and all operations should be carried -out behind an adequate shield. [Rabjohn Org Synth Coll Vol III 375 1955, see Kauer Org Synth Coll Vol IV 412 1963]. [Beilstein 3 III 233.] It is commercially available as a 40% solution in toluene. This reagent is useful in the Mitsunobu reaction [Mitsunobu Synthesis 1 1981, Gennari et al. J Am Chem Soc 108 6394 1986, Evans et al. J Am Chem Soc 108 6394 1986, Hughes Org React 42 335 1992, Dodge et al. Org Synth 73 110 1996, Hughes Org Prep Proc Int 28 127 1996, Ferguson & Marcelle J Am Chem Soc 128 4576 2006; see also di-tert-butyl azodicarboxylate above and DIAD below]. § A polystyrene supported DEAD version is commercially available with a loading of ~1.2mmol/g.