Diisopropyl azodicarboxylate, CAS No. 2446-83-5

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2446-83-5

Catalog No. EBD18031

CAS 2446-83-5

Name Diisopropyl azodicarboxylate

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Basic Information

Synonyms: azodicarbonicaciddiisopropylester azodicarboxylicaciddiisopropylester LABOTEST-BBLT00454155 diisopropylazodiformate Diisopropylazodicarboxylate Diazenedicarboxylicacid,bis(1-methylethyl)ester DIADAlternativetoDEAD DIISOPYLazodicarboxylate Diisopropylazodicarboxylat dipropan-2-yldiazene-1,2-dicarboxylate bis(1-methylethyl)(E)-diazene-1,2-dicarboxylate DIAD

Molecular Formula: C8H14N2O4

Molecular Weight: 202.21

MDL Number: MFCD00008875

Categories: Synthetic Chemistry > Basic Synthetic Reagents > Condensation Reagents

Product Description:

Diisopropyl azodicarboxylate (DIAD, CAS 2446-83-5) is an organic compound featuring an azo functional group (N=N) flanked by two isopropyl carboxylate esters. It is a red-orange liquid commonly used as a key reagent in organic synthesis. Its primary application is as an oxidizing agent and coupling reagent in the Mitsunobu reaction, where it facilitates the stereospecific conversion of alcohols into various functional groups (e.g., esters, ethers, thioethers) in combination with triphenylphosphine. DIAD also serves as a versatile synthetic building block for introducing azodicarboxylate moieties into target molecules, particularly in the preparation of heterocycles and pharmaceutical intermediates. Due to its high reactivity, DIAD is typically handled under inert atmospheres and stored at low temperatures. It is a standard reagent in both academic research and industrial process chemistry for constructing carbon-heteroatom bonds.

Physical Properties

Melting Point: 3-5 °C

Boiling Point: 75 °C/0.25 mmHg(lit.)

Flash Point: 106 °C

Density: 1.027 g/mL at 25 °C(lit.)

Solubility: insoluble

Refractivity: n20/D 1.420(lit.)

Storage: 2-8°C

Safety Information

Packing Level: III

Hazard Category: 9

Transport Codes: 3082