Diisopropyl azodicarboxylate

• Catalog No.: L10386
• CAS Number: 2446-83-5
• M. F.: C8H14N2O4
• M. W.: 202.20776
• Purity: 94%

SYNONYMS

• Title: 偶氮二甲酸二异丙酯
• IUPAC name: N-{[(propan-2-yloxy)carbonyl]imino}(propan-2-yloxy)formamide
• IUPAC Traditional name: diisopropyl azodicarboxylate
• Synonyms: Azodicarboxylic acid diisopropyl ester; DIAD

DATABASE IDS

• EC Number: 219-502-8
• MDL Number: MFCD00008875
• Beilstein Number: 1912326
• CAS Number: 2446-83-5

PROPERTIES

• Purity: 94%
• Boiling Point: 74-75°C/0.3mm
• Density: 1.027
• Flash Point: 160°C(320°F)
• Melting Point: 3-5°C
• Refractive Index: 1.4200
• GHS Hazard statements: H315-H319-H335-H411-H401
• European Hazard Symbols: Irritant (Xi)
• European Hazard Symbols: Nature polluting (N)
• GHS Precautionary statements: P261-P305+P351+P338-P302+P352-P321-P405-P501A
• Risk Statements: 36/37/38-51/53
• Safety Statements: 26-37-61
• Storage Warning: Light Sensitive
• TSCA Listed: 否
• Hazard Class: 9
• UN Number: UN3082
• Packing Group: III

REFERENCES

• Alternative to 'DEAD' (Diethyl azodicarboxylate, L19348), more stable at elevated temperatures. DIAD has been used in combination with Triphenylphosphine, L02502, in Mitsunobu-type reactions of alcohols with acids, amides, etc. In the Mitsunobu esterification reaction yields improve with increasing acid strength. For a discussion, see: J. Org. Chem., 61, 2967 (1996).
• For use in the regioselective, stereospecific Mitsunobu azidation of 1,2- and 1,3-diols with Trimethylsilyl azide, L00173, see: J. Org. Chem., 64, 6049 (1999).
• An extremely mild route to isocyanates involves treatment of an aliphtic primary amine with CO₂ to form the carbamate salt which reacts at low temperature with the Mitsunobu reagent from DIAD and PPh₃, giving the isocyanate in high yield. 2,6-Dialkylanilines also undergo the reaction if Bu₃P is used; the reaction failed with other anilines: Tetrahedron Lett., 40, 363 (1999).
• For reviews of the Mitsunobu reaction, see: Synthesis, 1 (1981); Org. React., 42, 335 (1992); Org. Prep. Proced. Int., 28, 127 (1996). For a brief feature on synthetic uses of Mitsunobu reagents, see: Synlett, 1221 (2003).