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			{{redirect|DIAD|the "Delivery Information Acquisition Device"|United Parcel Service}}
	{{chembox		{{chembox
			| Verifiedfields = changed
⚫	| verifiedrevid = 399903818
			| Watchedfields = changed
⚫	| Name = Diisopropyl azodicarboxylate
		⚫	| verifiedrevid = 443643693
⚫	| ImageFile = Diisopropyl azodicarboxylate.png
		⚫	| Name = Diisopropyl azodicarboxylate
	| ImageSize = 200px
	| ImageName = Diisopropyl azodicarboxylate		| ImageFile = Diisopropyl azodicarboxylate.svg
		⚫	| ImageName = Diisopropyl azodicarboxylate
	| ImageFile1 = Diisopropyl_azodicarboxylate-3d.png		| ImageFile1 = Diisopropyl_azodicarboxylate-3d.png
	| ImageSize1 = 200px
	| IUPACName = Diisopropyl azodicarboxylate		| IUPACName = Diisopropyl azodicarboxylate
	| OtherNames = DIAD		| OtherNames = DIAD
			| SystematicName = Propan-2-yl (''NE'')-''N''-propan-2-yloxycarbonyliminocarbamate<ref>https://pubchem.ncbi.nlm.nih.gov/compound/5363146#section=IUPAC-Name&fullscreen=true</ref>
	| Section1 = {{Chembox Identifiers
	| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}		| Section1 = {{Chembox Identifiers
			| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
	| ChemSpiderID = 4515532		| ChemSpiderID = 4515532
			| EINECS = 219-502-8
	| PubChem = 5363146		| 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+		| InChI = 1/C8H14N2O4/c1-5(2)13-7(11)9-10-8(12)14-6(3)4/h5-6H,1-4H3/b10-9+
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	| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}		| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
	| StdInChIKey = VVWRJUBEIPHGQF-MDZDMXLPSA-N		| StdInChIKey = VVWRJUBEIPHGQF-MDZDMXLPSA-N
			| CASNo_Ref = {{cascite|correct|CAS}}
	| CASNo = 2446-83-5		| CASNo = 2446-83-5
⚫	| SMILES = O=C(OC(C)C)\N=N/C(OC(C)C)=O
			| UNII_Ref = {{fdacite|correct|FDA}}
⚫	}}
			| UNII = 7W701BXX4K
⚫	| Section2 = {{Chembox Properties
		⚫	| SMILES = O=C(OC(C)C)\N=N/C(OC(C)C)=O
	| C=8|H=14|N=2|O=4
		⚫	}}
⚫	| Density = 1.027 g/cm<sup>3</sup>
		⚫	| Section2 = {{Chembox Properties
	| MeltingPt = 3-5 °C
	| BoilingPt = 75 °C at 0.25 mmHg		| C=8 | H=14 | N=2 | O=4
			| Appearance = Orange liquid
⚫	| Refractive Index = 1.418-1.422
		⚫	| Density = 1.027 g/cm<sup>3</sup>
	| Solubility = insoluble
			| MeltingPtC = 3 to 5
⚫	}}
			| BoilingPtC = 75
⚫	| Section3 = {{Chembox Hazards
			| BoilingPt_notes = at 0.25 mmHg
	| MainHazards =
		⚫	| RefractIndex = 1.418-1.422
	| EUClass = ] ('''F''')<br />] ('''Xi''')<br />Env. Danger ('''N''')
	| NFPA-H =		| Solubility = insoluble
		⚫	}}
	| NFPA-F =
		⚫	| Section3 = {{Chembox Hazards
	| NFPA-R =
			| GHSPictograms = {{GHS07}}{{GHS08}}{{GHS09}}
	| RPhrases = {{R5}}, {{R11}}, {{R36}}, {{R37}}, {{R38}}, {{R43}}, {{R51}}, {{R53}}
			| GHSSignalWord = Warning
	| SPhrases = {{S16}}, {{S26}}, {{S29}}, {{S36}}, {{S37}}, {{S39}}, {{S47}}, {{S61}}
			| HPhrases = {{H-phrases|315|319|335|373|411}}
	| FlashPt = 106°C
			| 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}}
	| Autoignition =
			| FlashPtC = 106
	| ExternalMSDS =		| ExternalSDS =
	}}		}}
	}}		}}
			'''Diisopropyl azodicarboxylate''' ('''DIAD''') is the ] ] of azodicarboxylic acid. It is used as a ] in the production of many ]s. It is often used with ] in the ],<ref>{{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 }}</ref> wherein it serves as a ] acceptor. It has also been used to generate aza-] adducts with acrylates.<ref>{{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 = ] | volume = 60 | issue = 9 | pages = 2083–2089 | doi = 10.1016/j.tet.2003.12.059 | year = 2004}}</ref> It can also serve as a selective ] of N-] groups in the presence of other protecting groups.<ref>{{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 = ] | year = 2004 | volume = 3 | issue = 3 | pages = 446–450 | doi = 10.1055/s-2004-815937}}</ref>
	'''Diisopropyl azodicarboxylate''' ('''DIAD''') is the ] ] of ]. It is used as a ] in the production of many ]s. It is often used in the ]<ref>
	{{citeweb
	| url = https://www.sigmaaldrich.com/catalog/search/ProductDetail/FLUKA/11626
	| title = Fluka DIAD on Sigma-Aldrich
	| accessdate = 2008-11-18
	}}
	</ref> where it serves as an ] of ] to ]. It has also be used to generate aza-] adducts with acrylates.<ref>
	{{cite journal | author = Shi, Min and Zhao, Gui-Ling | title = Aza-Baylis–Hillman reactions of diisopropyl azodicarboxylate or diethyl azodicarboxylate with acrylates and acrylonitrile | journal = ] | volume = 60 | issue = 9 | pages = 2083–2089 | doi = 10.1016/j.tet.2003.12.059 | year = 2004}}</ref> It can also serve as a selective ] of N-] groups in the presence of other protecting groups.<ref>
	{{cite journal | author = Kroutil, J.; Trnka, T.; and Cerny, M. | title = Improved procedure for the selective N-debenzylation of benzylamines by diisopropyl azodicarboxylate | journal = ] | year = 2004 | volume = 3 | issue = 3 | pages = 446–450 | doi = 10.1055/s-2004-815937}}</ref>
	It is sometimes preferred to ] (DEAD) because it is more ], and thus will not form ] byproducts.		It is sometimes preferred to ] (DEAD) because it is more ], and thus less likely to form ] byproducts.
			One notable use of this compound is in the synthesis of Bifenazate (Floramite®).{{cn|date=January 2021}}
	==References==		==References==
	{{reflist}}		{{reflist}}
	]		]
	]		]
			]
	{{organic-compound-stub}}
	]
	]