• USA Home
  • 225541 - Diisopropyl azodicarboxylate

EMAIL THIS PAGE TO A FRIEND
225541 Sigma-Aldrich

Diisopropyl azodicarboxylate

98%

Synonym: DIAD, Diisopropyl azodiformate

  • CAS Number 2446-83-5

  • Linear Formula (CH3)2CHOOCN=NCOOCH(CH3)2

  • Molecular Weight 202.21

  •  Beilstein/REAXYS Number 1912326

  •  MDL number MFCD00008875

  •  PubChem Substance ID 24853505

  •  NACRES NA.22

Purchase

Properties

Related Categories C-X Bond Formation (Non-Halogen), Chemical Reagents, Chemical Synthesis, Development Quantities for Research, Mitsunobu,
Quality Level   200
assay   98%
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

Description

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

Packaging

25, 100, 500 g in poly bottle

5 g in glass bottle

Safety & Documentation

Safety Information

Symbol 
Signal word 
Warning
Hazard statements 
Precautionary statements 
RIDADR 
UN 3082 9 / PGIII
WGK Germany 
2
Flash Point(F) 
222.8 °F
Flash Point(C) 
106 °C
Protocols & Articles

Articles

Reagents for the Mitsunobu Reaction

One of the most powerful and widely used carboncarbon bond forming reactions in organic synthesis is the Mitsunobu reaction.1 The Mitsunobu reaction is also useful in the preparation of other moietie...
ChemFiles Volume 4 Article 2
Keywords: Mitsunobu Reaction, Organic synthesis

Peer-Reviewed Papers
15

References

Related Products

related product

Product #

Description

Add to Cart

08168 Timestrip Plus 8 °C

Technical Service:

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Bulk Ordering & Pricing:

Need larger quantities for your development, manufacturing or research applications?