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2446-83-5 - Diisopropyl azodicarboxylate, 94% - Azodicarboxylic acid diisopropyl ester - DIAD - L10386 - Alfa Aesar

L10386 Diisopropyl azodicarboxylate, 94%

CAS-Nummer
2446-83-5
Synonyme
Azodicarboxylic acid diisopropyl ester
DIAD

Größe Preis ($) Menge Verfügbarkeit
25g 37,71
100g 87,55
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Diisopropyl azodicarboxylate, 94%

MDL
MFCD00008875
EINECS
219-502-8

Chemische Eigenschaften

Formel
(CH3)2CHO2C-N=N-CO2CH(CH3)2
Molmasse
202.21
Schmelzpunkt
3-5°
Siedepunkt
74-75°/0.3mm
Flammpunkt
160°(320°F)
Dichte
1.027
Brechungsindex
1.4200
Sensitivität
Light Sensitive
Löslichkeit
Immiscible with water.

Anwendungen

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.

Bemerkungen

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

Literaturverweise

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 Gefahren- und Sicherheitshinweise

Gefahrenhinweise (EU): H315-H319-H335-H411-H401

Causes skin irritation. Causes serious eye irritation. May cause respiratory irritation. Toxic to aquatic life with long lasting effects. Toxic to aquatic life.

Sicherheitshinweise: P261-P273-P280-P305+P351+P338-P304+P340-P362-P312-P405-P403+P233-P501a

Avoid breathing dust/fume/gas/mist/vapours/spray. Avoid release to the environment. Wear protective gloves/protective clothing/eye protection/face protection. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. IF INHALED: Remove to fresh air and keep at rest in a position comfortable for breathing. Take off contaminated clothing and wash before reuse. Call a POISON CENTER or doctor/physician if you feel unwell. Store locked up. Store in a well-ventilated place. Keep container tightly closed. Dispose of contents/container in accordance with local/regional/national/international regulations.

Weitere Referenzen

Beilstein
1912326
Gefahrenklasse
9
Verpackungsgruppe
III
Harmonized Tariff Code
2927.00
TSCA
No

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