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225541

Sigma-Aldrich

Diisopropyl azodicarboxylate

98%

Sinônimo(s):

DIAD, Diisopropyl azodiformate

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About This Item

Fórmula linear:
(CH3)2CHOOCN=NCOOCH(CH3)2
Número CAS:
2446-83-5
Peso molecular:
202.21
Beilstein:
1912326
Número MDL:
MFCD00008875
Código UNSPSC:
12352302
ID de substância PubChem:
24853505
NACRES:
NA.22

Nível de qualidade

200

Ensaio

98%

forma

liquid

Impurezas

≤2% dichloromethane

índice de refração

n20/D 1.420 (lit.)

pb

75 °C/0.25 mmHg (lit.)

densidade

1.027 g/mL at 25 °C (lit.)

temperatura de armazenamento

2-8°C

cadeia de caracteres 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+

chave InChI

VVWRJUBEIPHGQF-MDZDMXLPSA-N

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Descrição geral

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

Aplicação

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

Palavra indicadora

Warning

Frases de perigo

H315,H319,H335,H351,H411

Classificações de perigo

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

Órgãos-alvo

Respiratory system

Código de classe de armazenamento

10 - Combustible liquids

Classe de risco de água (WGK)

WGK 2

Ponto de fulgor (°F)

222.8 °F

Ponto de fulgor (°C)

106 °C

Equipamento de proteção individual

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

Certificados de análise (COA)

Busque Certificados de análise (COA) digitando o Número do Lote do produto. Os números de lote e remessa podem ser encontrados no rótulo de um produto após a palavra “Lot” ou “Batch”.

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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.
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