Substance
ID:736212
Names and Identifiers
Synonyms
DIAD偶氮二甲酸二异丙酯Diisopropyl azodicarboxylateAzodicarboxylic acid diisopropyl ester
IUPAC Traditional name
diisopropyl azodicarboxylate
IUPAC name
N-{[(propan-2-yloxy)carbonyl]imino}(propan-2-yloxy)formamide
Registration numbers
EC Number
MDL Number
Beilstein Number
CAS Number
Properties
Safety Information
Hazard Class
9
GHS Pictograms
Hazardous to the aquatic environment
Acute hazard, category1
Chronic hazard, categories 1,2
Acute toxicity (oral, dermal, inhalation), category 4
Skin irritation, category 2
Eye irritation, category 2
Skin sensitisation, category 1
Specific Target Organ Toxicity – Single exposure, category 3
GHS Hazard statements
H315-H319-H335-H411-H401
Safety Statements
26-37-61
Storage Warning
Light Sensitive
European Hazard Symbols
Irritant (Xi)
Nature polluting (N)Risk Statements
36/37/38-51/53
UN Number
UN3082
GHS Precautionary statements
P261-P305+P351+P338-P302+P352-P321-P405-P501A
TSCA Listed
否
Packing Group
III
Product Information
Purity
94%
Physical Property
Melting Point
3-5°C
Boiling Point
74-75°C/0.3mm
Refractive Index
1.4200
Density
1.027
Flash Point
160°C(320°F)
Molecule Details
No Data Available
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Molecular Spectra
No Data Available
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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).
• 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 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).
• 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).