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225541

Sigma-Aldrich

Diisopropyl azodicarboxylate

98%

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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
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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1 of 4

This Item
122130166804557811
Diisopropyl azodicarboxylate 98%

Sigma-Aldrich

225541

Diisopropyl azodicarboxylate

3,5-Dibromosalicylaldehyde 98%

Sigma-Aldrich

122130

3,5-Dibromosalicylaldehyde

Dibenzyl azodicarboxylate technical grade, 90%

Sigma-Aldrich

166804

Dibenzyl azodicarboxylate

2,4-Diisopropylphenol 98%

Sigma-Aldrich

557811

2,4-Diisopropylphenol

form

liquid

form

solid

form

solid

form

-

refractive index

n20/D 1.420 (lit.)

refractive index

-

refractive index

-

refractive index

n20/D 1.5130 (lit.)

bp

75 °C/0.25 mmHg (lit.)

bp

-

bp

-

bp

79-80 °C (lit.)

density

1.027 g/mL at 25 °C (lit.)

density

-

density

-

density

0.948 g/mL at 25 °C (lit.)

storage temp.

2-8°C

storage temp.

-

storage temp.

2-8°C

storage temp.

-

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 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

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