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870-50-8 - Di-tert-butyl azodicarboxylate, 98% - Azodicarboxylic acid di-tert-butyl ester - DTAD - L00294 - Alfa Aesar

L00294 Di-tert-butyl azodicarboxylate, 98%

Codice CAS
870-50-8
Sinonimi
Azodicarboxylic acid di-tert-butyl ester
DTAD

Dimensioni Prezzo ($) Quantità Disponibilità
5g 40,90
25g 144,00
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Di-tert-butyl azodicarboxylate, 98%

MDL
MFCD00015001
EINECS
212-796-9

Proprietà chimiche

Formula
(CH3)3CO2C-N=N-CO2C(CH3)3
Peso formula
230.27
Punto di fusione
89-92°
Sensibilità
Light Sensitive
Solubilità
Soluble in most organic solvents. Insoluble in water.

Applicazioni

Di-tert-butyl azodicarboxylate is a reagent used in the preparation of acyl hydrazinedicarboxylates. It is also used in the electrophilic amination of beta-keto esters catalyzed by an axially chiral guanidine. It serves as a precursor in an enantioselective synthesis of 3,6-dihyropyridazines employing organocatalysts such as L-proline or (S)-2-pyrrolidinyl tetrazole. It is also utilized in the asymmetric Friedel-Crafts amination through a chiral organocatalyst. Further, it acts as a reactant for preparation of hexapeptide key fragments through stereo selective selenocyclization/oxidative deselenylation reactions. In addition to this, it is employed as a starting material in the synthesis of pyrroloisoquinoline template through stereoselective N-acyliminium-mediated cyclization and enolate amination for preparation of peptidomimetic compounds and Barbier-type propargylation reactions.

Note

Light sensitive. Store in a cool place. Keep the container tightly closed in a dry and well-ventilated place. Incompatible with strong bases and alcohols.

Letteratura

Aza-dienophile. The ester groups are readily removed from adducts by acid: J. Org. Chem., 26, 4336 (1961); 38, 2043 (1973); 40, 563 (1975).

Useful "NH2 +" synthon for enantioselective amination reactions: J. Am. Chem. Soc., 108, 6394, 6395, 6397 (1986); Tetrahedron Lett., 29, 6765 (1988).

Mitsunobu reaction with alcohols gives a direct route to the corresponding N,N'-di-Boc protected hydrazine derivatives: Tetrahedron Lett., 37, 4327 (1996).

Kasaplar, P.; Ozkal, E.; Rodríguez-Escrich, C.; Pericàs, M. A. Enantioselective alpha-amination of 1,3-dicarbonyl compounds in batch and flow with immobilized thiourea organocatalysts. Green Chem. 2015, 17 (5), 3122-3129.

Yang, X.; Toste, F. D. Direct Asymmetric Amination of alpha-Branched Cyclic Ketones Catalyzed by a Chiral Phosphoric Acid. J. Am. Chem. Soc. 2015, 137 (9), 3205-3208.

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
1911434
Codice tariffe armonizzato
2927.00
TSCA
No

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