Diisopropyl azodicarboxylate

Diisopropyl azodicarboxylate
IUPAC name

Diisopropyl azodicarboxylate
Other names

DIAD
Identifiers
CAS number 2446-83-5
PubChem 5363146
ChemSpider 4515532 Y
Jmol-3D images Image 1
Image 2
Properties
Molecular formula C8H14N2O4
Molar mass 202.21 g mol−1
Density 1.027 g/cm3
Melting point

3-5 °C
Boiling point

75 °C at 0.25 mmHg
Solubility in water insoluble
Hazards
MSDS Sigma-Aldrich
EU classification Flammable (F)
Irritant (Xi)
Env. Danger (N)
R-phrases R5, R11, R36, R37, R38, R43, R51, R53
S-phrases S16, S26, S29, S36, S37, S39, S47, S61
Flash point 106°C
 Y (verify) (what is: Y/N?)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

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 be 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]

It is sometimes preferred to diethyl azodicarboxylate (DEAD) because it is more hindered, and thus will not form hydrazide byproducts.

References

  1. ^ "Fluka DIAD on Sigma-Aldrich". https://www.sigmaaldrich.com/catalog/search/ProductDetail/FLUKA/11626. Retrieved 2008-11-18. 
  2. ^ Shi, Min and 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.; and 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.