225541
Diisopropyl azodicarboxylate
98%
Synonym(s):
DIAD, Diisopropyl azodiformate
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About This Item
Linear Formula:
(CH3)2CHOOCN=NCOOCH(CH3)2
CAS Number:
Molecular Weight:
202.21
UNSPSC Code:
12352302
NACRES:
NA.22
PubChem Substance ID:
MDL number:
Beilstein/REAXYS Number:
1912326
Assay:
98%
Form:
liquid
Quality Level
assay
98%
form
liquid
impurities
≤2% dichloromethane
refractive index
n20/D 1.420 (lit.)
bp
75 °C/0.25 mmHg (lit.)
density
1.027 g/mL at 25 °C (lit.)
functional group
azo
storage temp.
2-8°C
SMILES string
CC(C)OC(=O)\N=N\C(=O)OC(C)C
InChI
1S/C8H14N2O4/c1-5(2)13-7(11)9-10-8(12)14-6(3)4/h5-6H,1-4H3/b10-9+
InChI key
VVWRJUBEIPHGQF-MDZDMXLPSA-N
General description
Reacted with dioxaphosphorinanes and iron catalyst to generate rearranged phosphonium ylide products.
Application
Reactant for preparation of:
- Chromenes resembling classical cannabinoids
- MK-3281 inhibitor of the hepatitis C virus NS5B polymerase
- Norbornene-based guanidine-rich polymers as mimcs of cell-penetrating peptides (CPP)
- Analogues of the Pseudomonas aeruginosa quorum-sensing molecule N-(3-Oxododecanoyl)-l-homoserine lactone with immunosuppressive but non-LasR-inducing properties
- Acceptor-donor-acceptor organic dyes for dye-sensitized solar cells
- 1,3-dioxane-2-carboxylic acid derivatives as PPARα/γ dual agonists
- Hydrazinophosphonates and hydrazinobisphosphonates via Mitsunobu and Arbuzov-type multicomponent application of the Morrison-Brunn-Huisgen betaine
Diisopropyl azodicarboxylate (DIAD) is a commonly used reagent in organic synthesis for the preparation of useful chemical intermediates. It is often used in the Mitsunobu and aza-Baylis-Hillman reaction. DIAD is also used as a selective deprotecting agent of N-benzyl groups.
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signalword
Warning
Hazard Classifications
Aquatic Chronic 2 - Carc. 2 - Eye Irrit. 2 - Skin Irrit. 2 - STOT RE 2 - STOT SE 3
target_organs
Respiratory system
Storage Class
10 - Combustible liquids
wgk
WGK 2
flash_point_f
222.8 °F
flash_point_c
106 °C
ppe
Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter
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Marcelle L Ferguson et al.
Journal of the American Chemical Society, 128(14), 4576-4577 (2006-04-06)
Allylic phosphonium ylides are readily generated by the combination of an allylic alcohol, a carbene, and a chlorophosphite. Here we demonstrate that these intermediates undergo a thermal [3,3]-rearrangement to provide single isomers of homoallylic phosphonates in good to excellent yields.
Zhi-Huang Qiu et al.
The Annals of thoracic surgery, 110(3), 925-932 (2020-01-29)
The efficacy of hemiarch replacement combined with a modified triple-branched stent graft in Debakey type I aortic dissection remains to be confirmed. From January 2016 to December 2017, 167 patients with acute Debakey type I aortic dissection underwent hemiarch replacement
Regina Kelmansky et al.
Acta biomaterialia, 53, 93-99 (2017-02-13)
Many bio-adhesive materials adhere weakly to tissue due to their high water content and weak structural integrity. Others provide desirable adhesive strength but suffer from rigid structure and lack of elasticity after administration. We have developed two water-free, liquid four-armed