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Diisopropyl azodicarboxylate is used as an important reagent in the production of many organic compounds. It is used in association with triphenyl phosphine in Mitsunobu reaction of alcohols, acids and amides. It acts as reactant in the preparation of chromenes resembling classical cannabinoids, norbornene-based guanidine-rich polymers and acceptor-donor-acceptor organic dyes.
Alternative to 'DEAD' (Diethyl azodicarboxylate, L19348), more stable at elevated temperatures. DIAD has been used in combination with Triphenylphosphine, L02502, in Mitsunobu-type reactions of alcohols with acids, amides, etc. In the Mitsunobu esterification reaction yields improve with increasing acid strength. For a discussion, see: J. Org. Chem., 61, 2967 (1996).
For use in the regioselective, stereospecific Mitsunobu azidation of 1,2- and 1,3-diols with Trimethylsilyl azide, L00173, see: J. Org. Chem., 64, 6049 (1999).
An extremely mild route to isocyanates involves treatment of an aliphtic primary amine with CO2 to form the carbamate salt which reacts at low temperature with the Mitsunobu reagent from DIAD and PPh3, giving the isocyanate in high yield. 2,6-Dialkylanilines also undergo the reaction if Bu3P is used; the reaction failed with other anilines: Tetrahedron Lett., 40, 363 (1999).
For reviews of the Mitsunobu reaction, see: Synthesis, 1 (1981); Org. React., 42, 335 (1992); Org. Prep. Proced. Int., 28, 127 (1996). For a brief feature on synthetic uses of Mitsunobu reagents, see: Synlett, 1221 (2003).
Ryu, I.; Tani, A.; Fukuyama, T.; Ravelli, D.; Montanaro, S.; Fagnoni, M. Efficient C-H/C-N and C-H/C-CO-N Conversion via Decatungstate-Photoinduced Alkylation of Diisopropyl Azodicarboxylate. Org. Lett. 2013, 15 (10), 2554-2557.
Hayashi, M.; Shibuya, M.; Iwabuchi, Y. Oxidation of Alcohols to Carbonyl Compounds with Diisopropyl Azodicarboxylate Catalyzed by Nitroxyl Radicals. J. Org. Chem. 2012, 76 (6), 3005-3009.
Hazard Statements: H315-H319-H335-H373
Causes skin irritation. Causes serious eye irritation. May cause respiratory irritation. May cause damage to organs through prolonged or repeated exposure.
Precautionary Statements: P260-P264b-P271-P280-P302+P352-P304+P340-P305+P351+P338-P312-P314-P332+P313-P337+P313-P362-P501c
Do not breathe dust/fume/gas/mist/vapours/spray. Wash face, hands and any exposed skin thoroughly after handling Use only outdoors or in a well-ventilated area. Wear protective gloves/protective clothing/eye protection/face protection. IF ON SKIN: Wash with plenty of soap and water. IF INHALED: Remove to fresh air and keep at rest in a position comfortable for breathing. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. Call a POISON CENTER or doctor/physician if you feel unwell. Get medical advice/attention if you feel unwell. If skin irritation occurs: Get medical advice/attention. If eye irritation persists: Take off contaminated clothing and wash before reuse. Dispose of contents/ container to an approved waste disposal plant