225541

Diisopropyl azodicarboxylate

98%

• Synonym(s): DIAD, Diisopropyl azodiformate
• Linear Formula: (CH₃)₂CHOOCN=NCOOCH(CH₃)₂
• CAS Number: 2446-83-5
• Molecular Weight: 202.21
• Beilstein: 1912326
• MDL number: MFCD00008875
• UNSPSC Code: 12352302
• PubChem Substance ID: 24853505
• NACRES: NA.22

Properties

• Quality Level: 200
• 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

Description

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

Safety Information

• Pictograms: GHS08,GHS07,GHS09
• Signal Word: Warning
• Hazard Statements: H315,H319,H335,H351,H373,H411
• Precautionary Statements: P202 - P260 - P273 - P302 + P352 - P305 + P351 + P338 - P308 + P313
• 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 Code: 10 - Combustible liquids
• WGK: WGK 2
• Flash Point(F): 222.8 °F
• Flash Point(C): 106 °C
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves