1,1'-(Azodicarbonyl)-dipiperidine, CAS No. 10465-81-3

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10465-81-3

Catalog No. EBD2068

CAS 10465-81-3

Name 1,1'-(Azodicarbonyl)-dipiperidine

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Basic Information

Synonyms: Azodicarboxylicaciddipiperidide 1,1-(Azodicarbonyl)dipiperidine 1,1'-(azodicarbonyl)-dipiperidine diazene-1,2-diylbis(piperidin-1-ylmethanone) 1,1'-[(E)-diazene-1,2-diyldicarbonyl]dipiperidine 1,1-(Azodicarbonyl)-Dipiperidine sr4077 1,1'-(azodicarbonyl)dipiperidine azodicarboxylicaciddipiperidine azodicarboxylicdipiperidide diphenylpiperidylcarboxylate azodicarboxylicaciddipiperidylester azodicarboxylic 1,1'-Azobis(N,N-dimethylformamide) 3-(N,N-Dimethylcarbamoylimido)-1,1-dimethylurea

Molecular Formula: C12H20N4O2

Molecular Weight: 252.32

MDL Number: MFCD00010111

Categories: Synthetic Chemistry > Basic Synthetic Reagents > Dehydrating and Drying Agents Synthetic Chemistry > Organic Building Blocks > Other Organic Building Blocks

Product Description:

1,1'-(Azodicarbonyl)dipiperidine (ADDP), also known as diethyl azodicarboxylate (DEAD) analog with piperidine substituents, is a yellow to orange crystalline solid. It is a member of the azo-dicarboxylate family, structurally characterized by a central azo group (-N=N-) flanked by two carbonyl groups, each connected to a piperidine ring. Its primary and most significant application is as a versatile reagent in organic synthesis, specifically in the Mitsunobu reaction. In this widely used transformation, ADDP, in combination with a phosphine (typically triphenylphosphine), serves as a dehydrating agent to facilitate the conversion of alcohols into esters, ethers, and other derivatives under mild conditions via an oxidation-reduction mechanism. It is valued as an alternative to the more common DEAD, sometimes offering advantages in terms of stability, solubility, or reaction selectivity. ADDP is also employed in other synthetic methodologies, including the preparation of hydrazine derivatives and as a dehydrogenation agent. As a specialized reagent, it is primarily handled in research and development laboratories rather than in large-scale industrial processes. It requires careful handling due to its potential shock sensitivity and exothermic decomposition properties.

Physical Properties

Melting Point: 134-136 °C(lit.)

Boiling Point: 366.4 °C at 760 mmHg

Flash Point: 175.4 °C

Density: 1.29 g/cm3

Analytical Data

Appearance: yellow crystalline powder