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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%

CAS Number
870-50-8
Synonyms
Azodicarboxylic acid di-tert-butyl ester
DTAD

Size Price ($) Quantity Availability
5g 41.30
25g 135.12
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Di-tert-butyl azodicarboxylate, 98%

MDL
MFCD00015001
EINECS
212-796-9

Chemical Properties

Formula
(CH3)3CO2C-N=N-CO2C(CH3)3
Formula Weight
230.27
Melting point
89-92°
Sensitivity
Light Sensitive
Solubility
Soluble in most organic solvents. Insoluble in water.

Applications

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.

Notes

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.

Literature References

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.

GHS Hazard and Precautionary Statements

Hazard Statements: H315-H319-H335

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

Precautionary Statements: P261-P280-P305+P351+P338-P304+P340-P362-P312-P321-P405-P403+P233-P501a

Avoid breathing dust/fume/gas/mist/vapours/spray. 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. Specific treatment (see label). 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.

Other References

Beilstein
1911434
Harmonized Tariff Code
2927.00
TSCA
No

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