225541

Diisopropyl azodicarboxylate

98%

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

Propriétés

• Niveau de qualité: 200
• Essai: 98%
• Forme: liquid
• Impuretés: ≤2% dichloromethane
• Indice de réfraction: n20/D 1.420 (lit.)
• pb: 75 °C/0.25 mmHg (lit.)
• Densité: 1.027 g/mL at 25 °C (lit.)
• Groupe fonctionnel: azo
• 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

Description

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

Informations sur la sécurité

• Pictogrammes: GHS08,GHS07,GHS09
• Mention d'avertissement: Warning
• Mentions de danger: H315,H319,H335,H351,H373,H411
• Conseils de prudence: P202 - P260 - P273 - P302 + P352 - P305 + P351 + P338 - P308 + P313
• 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