Diisopropyl azodicarboxylate

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Diisopropyl azodicarboxylate
Diisopropyl azodicarboxylate
Diisopropyl azodicarboxylate-3d.png
Names
IUPAC name
Diisopropyl azodicarboxylate
Other names
DIAD
Identifiers
3D model (Jmol)
ChemSpider
ECHA InfoCard 100.017.730
UNII
Properties
C8H14N2O4
Molar mass 202.21 g·mol−1
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
Safety data sheet Sigma-Aldrich
Flammable (F)
Irritant (Xi)
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R-phrases (outdated) R5, R11, R36, R37, R38, R43, R51, R53
S-phrases (outdated) S16, S26, S29, S36, S37, S39, S47, S61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).
N verify (what is YesYN ?)
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 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]

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

References[edit]

  1. ^ "Fluka DIAD on Sigma-Aldrich". 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.