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L10386 Diisopropyl azodicarboxylate, 94%

CAS Number
2446-83-5
Synonyms
Azodicarboxylic acid diisopropyl ester
DIAD

Stock No. Size Price ($) Quantity Availability
L10386-14 25g 44.00
L10386-22 100g 92.50
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Diisopropyl azodicarboxylate, 94%

MDL
MFCD00008875
EINECS
219-502-8

Chemical Properties

Formula
(CH3)2CHO2C-N=N-CO2CH(CH3)2
Formula Weight
202.21
Melting point
3-5°
Boiling Point
74-75°/0.3mm
Flash Point
160°(320°F)
Density
1.027
Refractive Index
1.4200
Storage & Sensitivity
Keep Cold. Light Sensitive.
Solubility
Immiscible with water.

Applications

Diisopropyl azodicarboxylate is used as an important reagent in the production of many organic compounds. It is used in association with triphenyl phosphine in Mitsunobu reaction of alcohols, acids and amides. It acts as reactant in the preparation of chromenes resembling classical cannabinoids, norbornene-based guanidine-rich polymers and acceptor-donor-acceptor organic dyes.

Notes

Store in cool place. Light sensitive. Incompatible with strong oxidizing agents, strong bases, alcohols and metallic salts. Decomposes violently at or above: 100 0C.

Literature 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).

Ryu, I.; Tani, A.; Fukuyama, T.; Ravelli, D.; Montanaro, S.; Fagnoni, M. Efficient C-H/C-N and C-H/C-CO-N Conversion via Decatungstate-Photoinduced Alkylation of Diisopropyl Azodicarboxylate. Org. Lett. 2013, 15 (10), 2554-2557.

Hayashi, M.; Shibuya, M.; Iwabuchi, Y. Oxidation of Alcohols to Carbonyl Compounds with Diisopropyl Azodicarboxylate Catalyzed by Nitroxyl Radicals. J. Org. Chem. 2012, 76 (6), 3005-3009.

GHS Hazard and Precautionary Statements

Hazard Statements: H315-H319-H335-H373

Causes skin irritation. Causes serious eye irritation. May cause respiratory irritation. May cause damage to organs through prolonged or repeated exposure.

Precautionary Statements: P260-P264b-P271-P280-P302+P352-P304+P340-P305+P351+P338-P312-P314-P332+P313-P337+P313-P362-P501c

Do not breathe dust/fume/gas/mist/vapours/spray. Wash face, hands and any exposed skin thoroughly after handling Use only outdoors or in a well-ventilated area. Wear protective gloves/protective clothing/eye protection/face protection. IF ON SKIN: Wash with plenty of soap and water. IF INHALED: Remove to fresh air and keep at rest in a position comfortable for breathing. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. Call a POISON CENTER or doctor/physician if you feel unwell. Get medical advice/attention if you feel unwell. If skin irritation occurs: Get medical advice/attention. If eye irritation persists: Take off contaminated clothing and wash before reuse. Dispose of contents/ container to an approved waste disposal plant

Other References

Beilstein
1912326
Hazard Class
9
Packing Group
III
Harmonized Tariff Code
2927.00
TSCA
No

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