All Photos(6)
Synonym(s):
DIAD, Diisopropyl azodiformate
Linear Formula:
(CH3)2CHOOCN=NCOOCH(CH3)2
CAS Number:
Molecular Weight:
202.21
Beilstein:
1912326
MDL number:
UNSPSC Code:
12352302
PubChem Substance ID:
NACRES:
NA.22
Recommended Products
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.)
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
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General description
Reacted with dioxaphosphorinanes and iron catalyst to generate rearranged phosphonium ylide products.
Application
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.
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
Signal Word
Warning
Hazard Statements
Precautionary Statements
Hazard Classifications
Aquatic Chronic 2 - Carc. 2 - Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3
Target Organs
Respiratory system
WGK
WGK 2
Flash Point(F)
222.8 °F
Flash Point(C)
106 °C
Personal Protective Equipment
dust mask type N95 (US), Eyeshields, Gloves
Certificates of Analysis (COA)
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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
Aza-Baylis-Hillman reactions of diisopropyl azodicarboxylate or diethyl azodicarboxylate with acrylates and acrylonitrile
Shi M and Zhao G-L
Tetrahedron, 60(9), 2083-2089 (2004)
Eun-Hye Kim et al.
International journal of molecular sciences, 21(10) (2020-05-28)
Cancer immunotherapy has been revolutionized by the development of monoclonal antibodies (mAbs) that inhibit interactions between immune checkpoint molecules, such as programmed cell-death 1 (PD-1), and its ligand PD-L1. However, mAb-based drugs have some drawbacks, including poor tumor penetration and
J Miles Blackburn et al.
Organic letters, 19(21), 6012-6015 (2017-10-20)
A general approach to access sulfamate esters through preparation of sulfamic acid salts, subsequent activation with triphenylphosphine ditriflate, and nucleophilic trapping is disclosed. The method proceeds in modest to excellent yields to incorporate nucleophiles derived from aliphatic alcohols and phenols.
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