Diisopropyl azodicarboxylate

98%

Sinônimo(s):

DIAD, Diisopropyl azodiformate

Sobre este item

Fórmula linear:

(CH₃)₂CHOOCN=NCOOCH(CH₃)₂

Número CAS:

2446-83-5

Peso molecular:

202.21

UNSPSC Code:

12352302

NACRES:

NA.22

PubChem Substance ID:

24853505

MDL number:

MFCD00008875

Beilstein/REAXYS Number:

1912326

Assay:

98%

Form:

liquid

Propriedades

Quality Segment

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

Descrição

General description

Reacted with dioxaphosphorinanes and iron catalyst to generate rearranged phosphonium ylide products.[1]

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

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.