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Diisopropyl azodicarboxylate

CAS No.:2446-83-5
Molecular Weight: 202.20800 Molecular Formula: C8H14N2O4

Description

Diisopropyl azodicarboxylate (DIAD) is the diisopropyl ester of azodicarboxylic acid. It is used as a reagent in the production of many organic compounds. It is often used in the Mitsunobu reaction where it serves as an oxidizer of triphenylphosphine to triphenylphosphine oxide. It has also been used to generate aza-Baylis-Hillman adducts with acrylates. It can also serve as a selective deprotectant of N-benzyl groups in the presence of other protecting groups. It is sometimes preferred to diethyl azodicarboxylate (DEAD) because it is more hindered, and thus less likely to form hydrazide byproducts.

Properties

Appearance:orange crystal or liquid
Density:1.02
Melting Point:41703ºC
Boiling Point:75ºC (0.2 mmHg)
Storage temp:2-8ºC
Vapour:0.00463mmHg at 25°C
Refractive Index:1.418-1.422
Flash Point:106ºC
Solubility:insoluble
Stability:Stable at room temperature in closed containers under normal storage and handling conditions.

Safety and Handling

RTECS:UN 3082

Hazard Class:III

Safety Statements:S16-S26-S29-S36/37/39-S47-S61

HS Code:29270000

Packing Group:III

WGK Germany:1

RIDADR:UN 3082

Risk Statements:R11; R36/37/38; R43; R5; R51/53

Hazard Codes:F

Signal Word:Warning

Symbol:GHS07, GHS08, GHS09

Caution Statement:P261; P273; P281; P305 + P351 + P338

Hazard Declaration:H315; H319; H335; H351; H373; H411

NMR Spectrum

Precursor and Product