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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

Mentions de danger

H315,H319,H335,H351,H411

Classification des risques

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

Certificats d'analyse (COA)

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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

J Miles Blackburn et al.
Organic letters, 19(21), 6012-6015 (2017-10-20)
A general approach to access sulfamate esters through preparation of sulfamic acid salts, subsequent activation with triphenylphosphine ditriflate, and nucleophilic trapping is disclosed. The method proceeds in modest to excellent yields to incorporate nucleophiles derived from aliphatic alcohols and phenols.
Eun-Hye Kim et al.
International journal of molecular sciences, 21(10) (2020-05-28)
Cancer immunotherapy has been revolutionized by the development of monoclonal antibodies (mAbs) that inhibit interactions between immune checkpoint molecules, such as programmed cell-death 1 (PD-1), and its ligand PD-L1. However, mAb-based drugs have some drawbacks, including poor tumor penetration and
Petia Atanasova et al.
Nanomaterials (Basel, Switzerland), 9(5) (2019-05-30)
The robust, anisotropic tobacco mosaic virus (TMV) provides a monodisperse particle size and defined surface chemistry. Owing to these properties, it became an excellent bio-template for the synthesis of diverse nanostructured organic/inorganic functional materials. For selective mineralization of the bio-template
Jorge J Llibre-Guerra et al.
JAMA network open, 2(12), e1917126-e1917126 (2019-12-12)
The amyloid/tau/neurodegeneration (A/T/N) framework uses cerebrospinal fluid (CSF) levels of total tau (tTau) as a marker of neurodegeneration and CSF levels of phosphorylated tau 181 (pTau181) as a marker of tau tangles. However, it is unclear whether CSF levels of
Marcelle L Ferguson et al.
Journal of the American Chemical Society, 128(14), 4576-4577 (2006-04-06)
Allylic phosphonium ylides are readily generated by the combination of an allylic alcohol, a carbene, and a chlorophosphite. Here we demonstrate that these intermediates undergo a thermal [3,3]-rearrangement to provide single isomers of homoallylic phosphonates in good to excellent yields.
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