Diisopropyl azodicarboxylate

Diisopropyl azodicarboxylate
	Diisopropyl azodicarboxylateDiisopropyl azodicarboxylate
	File:Diisopropyl azodicarboxylate-3d.png
Names
	IUPAC name Diisopropyl azodicarboxylate
	Systematic IUPAC name Propan-2-yl (NE)-N-propan-2-yloxycarbonyliminocarbamate
	Other names DIAD
Identifiers
CAS Number	2446-83-5 check;
3D model (JSmol)	Interactive image; Interactive image;
ChemSpider	4515532 check;
ECHA InfoCard	Lua error in Module:Wikidata at line 880: attempt to index field 'wikibase' (a nil value). Lua error in Module:Wikidata at line 880: attempt to index field 'wikibase' (a nil value).Lua error in Module:EditAtWikidata at line 29: attempt to index field 'wikibase' (a nil value).
EC Number	219-502-8;
E number	Lua error in Module:Wikidata at line 880: attempt to index field 'wikibase' (a nil value).
PubChem CID	5363146;
UNII	7W701BXX4K check;
CompTox Dashboard (EPA)	{{#property:P3117}}Lua error in Module:EditAtWikidata at line 29: attempt to index field 'wikibase' (a nil value).;
	InChI InChI=1S/C8H14N2O4/c1-5(2)13-7(11)9-10-8(12)14-6(3)4/h5-6H,1-4H3/b10-9+ check Key: VVWRJUBEIPHGQF-MDZDMXLPSA-N check; 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
Appearance	Orange liquid
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
	GHS labelling:
Pictograms	GHS07: Exclamation markGHS08: Health hazardGHS09: Environmental hazard
Signal word	Warning
Hazard statements	H315, H319, H335, H373, H411
Precautionary statements	P260, P261, P264, P271, P273, P280, P302+P352, P304+P340, P305+P351+P338, P312, P314, P321, P332+P313, P337+P313, P362, P391, P403+P233, P405, P501
Flash point	106 °C (223 °F; 379 K)
Safety data sheet (SDS)	Sigma-Aldrich
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). ☒ verify (what is check☒ ?) 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 with triphenylphosphine in the Mitsunobu reaction,^[2] wherein it serves as a hydride acceptor. It has also been used to generate aza-Baylis-Hillman adducts with acrylates.^[3] It can also serve as a selective deprotectant of N-benzyl groups in the presence of other protecting groups.^[4]

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®).^{[citation needed]}

References

^ https://pubchem.ncbi.nlm.nih.gov/compound/5363146#section=IUPAC-Name&fullscreen=true
^ Lua error in Module:Citation/CS1/Configuration at line 2172: attempt to index field '?' (a nil value).
^ Lua error in Module:Citation/CS1/Configuration at line 2172: attempt to index field '?' (a nil value).
^ Lua error in Module:Citation/CS1/Configuration at line 2172: attempt to index field '?' (a nil value).

[1] ttps://pubchem.ncbi.nlm.nih.gov/compound/5363146#section=IUPAC-Name&fullscreen=true

[2] Lua error in Module:Citation/CS1/Configuration at line 2172: attempt to index field '?' (a nil value).

[3] Lua error in Module:Citation/CS1/Configuration at line 2172: attempt to index field '?' (a nil value).

[4] Lua error in Module:Citation/CS1/Configuration at line 2172: attempt to index field '?' (a nil value).

[1]

[2]

[3]

[4]

Names
Diisopropyl azodicarboxylate Diisopropyl azodicarboxylate
File:Diisopropyl azodicarboxylate-3d.png
IUPAC name Diisopropyl azodicarboxylate
Systematic IUPAC name Propan-2-yl (NE)-N-propan-2-yloxycarbonyliminocarbamate^[1]
Other names DIAD
Identifiers
CAS Number	2446-83-5^checkY
3D model (JSmol)	Interactive image Interactive image
ChemSpider	4515532^checkY
ECHA InfoCard	Lua error in Module:Wikidata at line 880: attempt to index field 'wikibase' (a nil value). Lua error in Module:Wikidata at line 880: attempt to index field 'wikibase' (a nil value).Lua error in Module:EditAtWikidata at line 29: attempt to index field 'wikibase' (a nil value).
EC Number	219-502-8
E number	Lua error in Module:Wikidata at line 880: attempt to index field 'wikibase' (a nil value).
PubChem CID	5363146
UNII	7W701BXX4K^checkY
CompTox Dashboard (EPA)	{{#property:P3117}}Lua error in Module:EditAtWikidata at line 29: attempt to index field 'wikibase' (a nil value).
InChI InChI=1S/C8H14N2O4/c1-5(2)13-7(11)9-10-8(12)14-6(3)4/h5-6H,1-4H3/b10-9+^checkY Key: VVWRJUBEIPHGQF-MDZDMXLPSA-N^checkY 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
Appearance	Orange liquid
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 (n_D)	1.418-1.422
Hazards
GHS labelling:
Pictograms	GHS07: Exclamation markGHS08: Health hazardGHS09: Environmental hazard
Signal word	Warning
Hazard statements	H315, H319, H335, H373, H411
Precautionary statements	P260, P261, P264, P271, P273, P280, P302+P352, P304+P340, P305+P351+P338, P312, P314, P321, P332+P313, P337+P313, P362, P391, P403+P233, P405, P501
Flash point	106 °C (223 °F; 379 K)
Safety data sheet (SDS)	Sigma-Aldrich
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). ☒N verify (what is ^checkY☒N ?) Infobox references

Diisopropyl azodicarboxylate

References

Navigation menu

Search