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Sigma-Aldrich

Diisopropyl azodicarboxylate

98%

Synonym(s):

DIAD, Diisopropyl azodiformate

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About This Item

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

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.)

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

H315,H319,H335,H351,H411

Hazard Classifications

Aquatic Chronic 2 - Carc. 2 - Eye Irrit. 2 - Skin Irrit. 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

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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