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225541

Sigma-Aldrich

Diisopropyl azodicarboxylate

98%

Synonyme(s) :

DIAD, Diisopropyl azodiformate

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About This Item

Formule linéaire :
(CH3)2CHOOCN=NCOOCH(CH3)2
Numéro CAS:
2446-83-5
Poids moléculaire :
202.21
Numéro Beilstein :
1912326
Numéro MDL:
MFCD00008875
Code UNSPSC :
12352302
ID de substance PubChem :
24853505
Nomenclature NACRES :
NA.22

Niveau de qualité

200

Pureté

98%

Forme

liquid

Impuretés

≤2% dichloromethane

Indice de réfraction

n20/D 1.420 (lit.)

Point d'ébullition

75 °C/0.25 mmHg (lit.)

Densité

1.027 g/mL at 25 °C (lit.)

Température de stockage

2-8°C

Chaîne SMILES 

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+

Clé InChI

VVWRJUBEIPHGQF-MDZDMXLPSA-N

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Description générale

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

Pictogrammes

Health hazardExclamation markEnvironment
GHS08,GHS07,GHS09

Mention d'avertissement

Warning

Classification des risques

Aquatic Chronic 2 - Carc. 2 - Eye Irrit. 2 - Skin Irrit. 2 - STOT RE 2 - STOT SE 3

Organes cibles

Respiratory system

Code de la classe de stockage

10 - Combustible liquids

Classe de danger pour l'eau (WGK)

WGK 2

Point d'éclair (°F)

222.8 °F

Point d'éclair (°C)

106 °C

Équipement de protection individuelle

Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter

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Certificats d'analyse (COA)

Lot/Batch Number
SHBN8649
SHBN8646
WXBD2123V
WXBD4743V
WXBD1204V

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Diethyl azodicarboxylate, polymer-bound 100-200 mesh, extent of labeling: 1.0-1.5 mmol/g loading, 1 % cross-linked with divinylbenzene

Sigma-Aldrich

561851

Diethyl azodicarboxylate, polymer-bound

Phthalimide ≥99%

Sigma-Aldrich

240230

Phthalimide

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