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

L10386 Diisopropyl azodicarboxylate, 94%

Codice CAS
2446-83-5
Sinonimi
Azodicarboxylic acid diisopropyl ester
DIAD

Dimensioni Prezzo ($) Quantità Disponibilità
25g 42,30
100g 88,00
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Diisopropyl azodicarboxylate, 94%

MDL
MFCD00008875
EINECS
219-502-8

Proprietà chimiche

Formula
(CH3)2CHO2C-N=N-CO2CH(CH3)2
Peso formula
202.21
Punto di fusione
3-5°
Punto di ebollizione
74-75°/0.3mm
Punto di infiammabilità
160°(320°F)
Densità
1.027
Indice di rifrazione
1.4200
Sensibilità
Light Sensitive
Solubilità
Immiscible with water.

Applicazioni

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.

Note

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

Letteratura

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.

Rischio GHS e dichiarazioni precauzionali

Dichiarazioni di rischio (UE): H315-H319-H335

Causes skin irritation. Causes serious eye irritation. May cause respiratory irritation.

Dichiarazioni precauzionali: P261-P280a-P305+P351+P338-P304+P340-P405-P501a

Avoid breathing dust/fume/gas/mist/vapours/spray. Wear protective gloves and eye/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. Store locked up. Dispose of contents/container in accordance with local/regional/national/international regulations.

Altri riferimenti

Beilstein
1912326
Classe di rischio
9
Gruppo di imballaggio
III
Codice tariffe armonizzato
2927.00
TSCA
No

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