3D model (JSmol)
|Molar mass||202.21 g·mol−1|
|Melting point||3 to 5 °C (37 to 41 °F; 276 to 278 K)|
|Boiling point||75 °C (167 °F; 348 K) at 0.25 mmHg|
Refractive index (nD)
|Safety data sheet||Sigma-Aldrich|
Env. Danger (N)
|R-phrases (outdated)||R5, R11, R36, R37, R38, R43, R51, R53|
|S-phrases (outdated)||S16, S26, S29, S36, S37, S39, S47, S61|
|Flash point||106 °C (223 °F; 379 K)|
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
|what is ?)(|
Diisopropyl azodicarboxylate (DIAD) is the diisopropyl ester of azodicarboxylic acid. It is used as a reagent in the production of many organic compounds. It is often used in the Mitsunobu reaction where it serves as an oxidizer of triphenylphosphine to triphenylphosphine oxide. It has also been used to generate aza-Baylis-Hillman adducts with acrylates. It can also serve as a selective deprotectant of N-benzyl groups in the presence of other protecting groups.
- "Fluka DIAD on Sigma-Aldrich". Retrieved 2008-11-18.
- Shi, Min; Zhao, Gui-Ling (2004). "Aza-Baylis–Hillman reactions of diisopropyl azodicarboxylate or diethyl azodicarboxylate with acrylates and acrylonitrile". Tetrahedron. 60 (9): 2083–2089. doi:10.1016/j.tet.2003.12.059.
- Kroutil, J.; Trnka, T.; Cerny, M. (2004). "Improved procedure for the selective N-debenzylation of benzylamines by diisopropyl azodicarboxylate". Synthesis. 3 (3): 446–450. doi:10.1055/s-2004-815937.