Diisopropyl azodicarboxylate
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| Names | |
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| IUPAC name
Diisopropyl azodicarboxylate
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| Other names
DIAD
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| Identifiers | |
2446-83-5  |
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| ChemSpider | 4515532 |
| Jmol 3D model | Interactive image Interactive image |
| PubChem | 5363146 |
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| 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 | |
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Refractive index (nD)
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1.418-1.422 |
| Vapor pressure | {{{value}}} |
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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
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