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 ;
	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	202.21 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
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EU classification (DSD) (outdated)	Flammable (F); Irritant (Xi); Env.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R-phrases (outdated)	R5, R11, R36, R37, R38, R43, R51, R53
S-phrases (outdated)	S16, S26, S29, S36, S37, S39, S47, S61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).
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	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

↑ "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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