Diisopropyl azodicarboxylate
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{{chembox
| Verifiedfields = changed
| Watchedfields = changed
| verifiedrevid = 443643693
| Name = Diisopropyl azodicarboxylate
| ImageFile = Diisopropyl azodicarboxylate.svg
| ImageName = Diisopropyl azodicarboxylate
| ImageFile1 = Diisopropyl_azodicarboxylate-3d.png
| IUPACName = Diisopropyl azodicarboxylate
| OtherNames = DIAD
| SystematicName = Propan-2-yl (NE)-N-propan-2-yloxycarbonyliminocarbamatehttps://pubchem.ncbi.nlm.nih.gov/compound/5363146#section=IUPAC-Name&fullscreen=true
| Section1 = {{Chembox Identifiers
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 4515532
| EINECS = 219-502-8
| PubChem = 5363146
| InChI = 1/C8H14N2O4/c1-5(2)13-7(11)9-10-8(12)14-6(3)4/h5-6H,1-4H3/b10-9+
| InChIKey = VVWRJUBEIPHGQF-MDZDMXLPBM
| SMILES1 = O=C(/N=N/C(=O)OC(C)C)OC(C)C
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/C8H14N2O4/c1-5(2)13-7(11)9-10-8(12)14-6(3)4/h5-6H,1-4H3/b10-9+
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = VVWRJUBEIPHGQF-MDZDMXLPSA-N
| CASNo_Ref = {{cascite|correct|CAS}}
| CASNo = 2446-83-5
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 7W701BXX4K
| SMILES = O=C(OC(C)C)\N=N/C(OC(C)C)=O
}}
| Section2 = {{Chembox Properties
| C=8 | H=14 | N=2 | O=4
| Appearance = Orange liquid
| Density = 1.027 g/cm3
| MeltingPtC = 3 to 5
| BoilingPtC = 75
| BoilingPt_notes = at 0.25 mmHg
| RefractIndex = 1.418-1.422
| Solubility = insoluble
}}
| Section3 = {{Chembox Hazards
| GHSPictograms = {{GHS07}}{{GHS08}}{{GHS09}}
| GHSSignalWord = Warning
| HPhrases = {{H-phrases|315|319|335|373|411}}
| PPhrases = {{P-phrases|260|261|264|271|273|280|302+352|304+340|305+351+338|312|314|321|332+313|337+313|362|391|403+233|405|501}}
| FlashPtC = 106
| ExternalSDS = [http://www.palomar.edu/ehs/Chemistry%20MSDS/DIISOPROPYL%20AZODICARBOXYLATE.pdf Sigma-Aldrich]
}}
}}
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,{{cite web | url = https://www.sigmaaldrich.com/catalog/search/ProductDetail/FLUKA/11626 | title = luka DIAD on Sigma-Aldrich | accessdate = 2008-11-18 | archive-date = 2008-04-24 | archive-url = https://web.archive.org/web/20080424095534/http://www.sigmaaldrich.com/catalog/search/ProductDetail/FLUKA/11626 | url-status = dead }} wherein it serves as a hydride acceptor. It has also been used to generate aza-Baylis-Hillman adducts with acrylates.{{cite journal |author1=Shi, Min |author2=Zhao, Gui-Ling | title = Aza-Baylis–Hillman reactions of diisopropyl azodicarboxylate or diethyl azodicarboxylate with acrylates and acrylonitrile | journal = Tetrahedron | volume = 60 | issue = 9 | pages = 2083–2089 | doi = 10.1016/j.tet.2003.12.059 | year = 2004}} It can also serve as a selective deprotectant of N-benzyl groups in the presence of other protecting groups.{{cite journal |author1=Kroutil, J. |author2=Trnka, T. |author3=Cerny, M. | title = Improved procedure for the selective N-debenzylation of benzylamines by diisopropyl azodicarboxylate | journal = Synthesis | year = 2004 | volume = 3 | issue = 3 | pages = 446–450 | doi = 10.1055/s-2004-815937}}
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®).{{cn|date=January 2021}}