Diisopropyl azodicarboxylate

Diisopropyl azodicarboxylate
Names
	IUPAC name Diisopropyl azodicarboxylate
	Other names DIAD
Identifiers
CAS Number	2446-83-5 ;
3D model (JSmol)	Interactive image; Interactive image;
ChemSpider	4515532 ;
ECHA InfoCard	100.017.730
PubChem CID	5363146;
UNII	7W701BXX4K ;
CompTox Dashboard (EPA)	DTXSID50894754 ;
	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−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
Solubility in water	insoluble
Refractive index (nD)	1.418-1.422
Hazards
Safety data sheet	Sigma-Aldrich
EU classification (DSD) (outdated)	Flammable (F); Irritant (Xi); Env.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R-phrases (outdated)	R5, R11, R36, R37, R38, R43, R51, R53
S-phrases (outdated)	S16, S26, S29, S36, S37, S39, S47, S61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).
	verify (what is ?)
	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.

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

References

"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.

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[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.