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Diisopropyl azodicarboxylate

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Diisopropyl azodicarboxylate
Diisopropyl azodicarboxylate
Diisopropyl azodicarboxylate
Names
IUPAC name Diisopropyl azodicarboxylate
Systematic IUPAC name Propan-2-yl (NE)-N-propan-2-yloxycarbonyliminocarbamate
Other names DIAD
Identifiers
CAS Number
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.017.730 Edit this at Wikidata
EC Number
  • 219-502-8
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C8H14N2O4/c1-5(2)13-7(11)9-10-8(12)14-6(3)4/h5-6H,1-4H3/b10-9+Key: VVWRJUBEIPHGQF-MDZDMXLPSA-N
  • 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
SMILES
  • 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
Chemical formula C8H14N2O4
Molar mass 202.210 g·mol
Appearance Orange liquid
Density 1.027 g/cm
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
Solubility in water insoluble
Refractive index (nD) 1.418-1.422
Hazards
GHS labelling:
Pictograms GHS07: Exclamation markGHS08: Health hazardGHS09: Environmental hazard
Signal word Warning
Hazard statements H315, H319, H335, H373, H411
Precautionary statements 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 , 100 kPa). ☒N verify (what is  ?) Infobox references
Chemical compound

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 with triphenylphosphine in the Mitsunobu reaction, wherein it serves as a hydride acceptor. 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.

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. https://pubchem.ncbi.nlm.nih.gov/compound/5363146#section=IUPAC-Name&fullscreen=true
  2. "luka DIAD on Sigma-Aldrich". Archived from the original on 2008-04-24. Retrieved 2008-11-18.
  3. 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.
  4. 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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