| Description | Diethyl azodicarboxylate, conventionally abbreviated as DEAD and sometimes as DEADCAT, is an organic compound with the structural formula CH3CH2O2CN=NCO2CH2CH3. Its molecular structure consists of a central azo functional group, RN=NR, flanked by two ethyl ester groups. This orange-red liquid is a valuable reagent but also quite dangerous and explodes upon heating. |
| Synonyms | DEAD, Diethyl diazenedicarboxylate, Ethyl azodicarboxylate, Azodiformic acid diethyl ester |
| molecular weight | 174.15 |
| Molecular formula | C6H10N2O4 |
| CAS | 4143-61-7 |
| Storage | Powder: -20°C for 3 years | In solvent: -80°C for 1 year | Shipping with blue ice. |
| References | 1. Aly AA, Hassan AA, Mohamed NK, Ramadan M, Brown AB, Abd El-Aal AS, Bräse S, Nieger M. Regioselective formation of 1,2,4-triazoles by the reaction of amidrazones in the presence of diethyl azodicarboxylate and catalyzed by triethylamine. Mol Divers. 2018 Aug 13. doi: 10.1007/s11030-018-9868-6. [Epub ahead of print] PubMed PMID: 30105556. 2. Hirose D, Gazvoda M, Košmrlj J, Taniguchi T. Systematic Evaluation of 2-Arylazocarboxylates and 2-Arylazocarboxamides as Mitsunobu Reagents. J Org Chem. 2018 Apr 20;83(8):4712-4729. doi: 10.1021/acs.joc.8b00486. Epub 2018 Apr 5. PubMed PMID: 29570289. 3. Bain RM, Sathyamoorthi S, Zare RN. "On-Droplet" Chemistry: The Cycloaddition of Diethyl Azodicarboxylate and Quadricyclane. Angew Chem Int Ed Engl. 2017 Nov 20;56(47):15083-15087. doi: 10.1002/anie.201708413. Epub 2017 Oct 24. PubMed PMID: 28992393. 4. Wang M, Nudelman F, Matthes RR, Shaver MP. Frustrated Lewis Pair Polymers as Responsive Self-Healing Gels. J Am Chem Soc. 2017 Oct 11;139(40):14232-14236. doi: 10.1021/jacs.7b07725. Epub 2017 Sep 27. PubMed PMID: 28915038. |