Diethyl Azodicarboxylate

• CAT Number: R047138
• CAS Number: 1972-28-7
• Molecular Formula: C₆H₁₀N₂O₄
• Molecular Weight: 174.15
• Purity: ≥95%
• Synonyms: 1,2-Diazenedicarboxylic Acid 1,2-Diethyl Ester; 1,2-Ethoxycarbonyl Diazene; Azodicarboxylic Acid Diethyl Ester; DEAD; Diethoxycarbonyldiazene; Diethyl Azodiformate; Diethyl Diazenedicarboxylate; Diethyl Diazodicarboxylate; NSC 3474; NSC 679015; Unifo
• Storage: Room temperature
• IUPAC Name: ethyl (NE)-N-ethoxycarbonyliminocarbamate
• InChI: InChI=1S/C6H10N2O4/c1-3-11-5(9)7-8-6(10)12-4-2/h3-4H2,1-2H3/b8-7+
• InChIKey: FAMRKDQNMBBFBR-BQYQJAHWSA-N
• SMILES: CCOC(=O)/N=N/C(=O)OCC

Diethyl azodicarboxylate (Cat No.:R047138) is a yellow-orange liquid reagent widely used in organic synthesis, particularly in the Mitsunobu reaction, where it facilitates the formation of carbon–oxygen, carbon–nitrogen, and carbon–carbon bonds. It contains an azo group (-N=N-) flanked by two diethyl ester groups, making it a strong electrophile and radical acceptor. DEAD is also utilized in cycloaddition, oxidative coupling, and ene reactions. Due to its high reactivity and potential explosiveness, it must be handled with care. Its versatility makes it a valuable tool in pharmaceutical and fine chemical synthesis.