Diisopropyl azodicarboxylate
[CAS# 2446-83-5]

Identification

• Classification: Chemical reagent >> Organic reagent >> Ester >> Propyl esters
• Name: Diisopropyl azodicarboxylate
• Synonyms: DIAD
• Molecular Formula: C₈H₁₄N₂O₄
• Molecular Weight: 202.21
• CAS Registry Number: 2446-83-5
• EC Number: 219-502-8
• SMILES: CC(C)OC(=O)/N=N/C(=O)OC(C)C

Properties

• Density: 1.02
• Melting point: 3-5 °C
• Boiling point: 75 °C (0.2 mmHg)
• Refractive index: 1.418-1.422
• Flash point: 106 °C
• Water solubility: insoluble

Safety Data

• Hazard Symbols: GHS07;GHS08 Warning
• Risk Statements: H315-H319-H335-H373-H411
• Safety Statements: P260-P261-P264-P264+P265-P271-P273-P280-P302+P352-P304+P340-P305+P351+P338-P319-P321-P332+P317-P337+P317-P362+P364-P391-P403+P233-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Skin irritation	Skin Irrit.	2	H315
Eye irritation	Eye Irrit.	2	H319
Chronic hazardous to the aquatic environment	Aquatic Chronic	2	H411
Specific target organ toxicity - single exposure	STOT SE	3	H335
Specific target organ toxicity - repeated exposure	STOT RE	2	H373
Carcinogenicity	Carc.	2	H351
Specific target organ toxicity - single exposure	STOT SE	3	H371

• Transport Information: UN 3082

Discovery and Applications

Diisopropyl azodicarboxylate (DIAD) is a versatile compound that has had a major impact on organic synthesis since its discovery. First synthesized in 1960 by J. W. Cook and W. R. Benson, DIAD has become a cornerstone reagent in organic chemistry, highly regarded for its efficiency and selectivity in a wide range of reactions.

References

2024. Synthetic studies on the tetrasubstituted D-ring of cystobactamids lead to potent terephthalic acid antibiotics. *Communications Chemistry*, 7(1).
DOI: 10.1038/s42004-024-01337-6

2023. (Parallel) kinetic resolution of 3,3-disubstituted indolines via organocatalyzed reactions with azodicarboxylates. *Science China Chemistry*, 66(11).
DOI: 10.1007/s11426-023-1810-9

2024. Synthesis of oligosaccharides from terminal B. pertussis LPS pentasaccharide and definition of the minimal epitope recognized by anti-pertussis antibodies. *Glycoconjugate Journal*, 41(3).
DOI: 10.1007/s10719-024-10160-z