Diisopropyl azodicarboxylate

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,[1] where it serves as an oxidizer of triphenylphosphine to triphenylphosphine oxide. It has also been used to generate aza-Baylis-Hillman adducts with acrylates.[2] It can also serve as a selective deprotectant of N-benzyl groups in the presence of other protecting groups.[3]

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Diisopropyl azodicarboxylate
Diisopropyl azodicarboxylate
Names
IUPAC name
Diisopropyl azodicarboxylate
Other names
DIAD
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.017.730
EC Number
  • 219-502-8
UNII
  • InChI=1S/C8H14N2O4/c1-5(2)13-7(11)9-10-8(12)14-6(3)4/h5-6H,1-4H3/b10-9+ checkY
    Key: VVWRJUBEIPHGQF-MDZDMXLPSA-N checkY
  • InChI=1/C8H14N2O4/c1-5(2)13-7(11)9-10-8(12)14-6(3)4/h5-6H,1-4H3/b10-9+
    Key: VVWRJUBEIPHGQF-MDZDMXLPBM
  • O=C(OC(C)C)\N=N/C(OC(C)C)=O
  • O=C(/N=N/C(=O)OC(C)C)OC(C)C
Properties
C8H14N2O4
Molar mass 202.210 g·mol−1
Appearance Orange liquid
Density 1.027 g/cm3
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
insoluble
1.418-1.422
Hazards
GHS labelling:
GHS07: Exclamation markGHS08: Health hazardGHS09: Environmental hazard
Warning
H315, H319, H335, H373, H411
P260, P261, P264, P271, P273, P280, P302+P352, P304+P340, P305+P351+P338, P312, P314, P321, P332+P313, P337+P313, P362, P391, P403+P233, P405, P501
Flash point 106 °C (223 °F; 379 K)
Safety data sheet (SDS) Sigma-Aldrich
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)
Infobox references

It is sometimes preferred to diethyl azodicarboxylate (DEAD) because it is more hindered, and thus less likely to form hydrazide byproducts.

One notable use of this compound is in the synthesis of Bifenazate (Floramite®).

References
  1. "luka DIAD on Sigma-Aldrich". Archived from the original on 2008-04-24. Retrieved 2008-11-18.
  2. 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.
  3. 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.
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