L19348

Diethyl azodicarboxylate, 97%

CAS Number 1972-28-7 Synonyms
  • Azodicarboxylic acid diethyl ester
  • DEAD

 
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Diethyl azodicarboxylate, 97%

MDL: MFCD00009103
EINECS: 217-821-7

Chemical Properties

Formula: C6H10N2O4  Density: 1.106
Formula weight: 174.16  Refractive Index: 1.4210
Boiling point: 106°/13mm Sensitivity: Air & Light Sensitive
Flash point: 85°(185°F) 

Literature References

Explosion risk by heating undiluted material.

Dehydrogenating agent and aza-dienophile. Oxidizes alcohols to aldehydes, thiols to disulfides and hydrazo to azo groups: J. Am. Chem. Soc., 88, 2328 (1966). Arylhydroxylamines are converted in high yield to nitroso compounds: Chem. Commun., 199 (1967).

Undergoes pericyclic reactions with alkenes and dienes via both ene and Diels-Alder processes. For further details and references, see: Encyclopedia of Reagents for Organic Synthesis, L. A. Paquette, Ed., Wiley, Chichester (1995), vol. 3, p. 1790.

Secondary and tertiary amines have been dealkylated by reaction with DEAD under mild conditions, followed by acid hydrolysis: J. Org. Chem., 38, 1652 (1973).

In combination with Triphenyl­phosphine, L02502, is widely used in the Mitsunobu reaction for activation of primary and secondary alcohols by formation of the alkoxyphosphonium salts, which behave as versatile alkylating agents under mild SN2 conditions: reactions normally proceed with inversion of configuration. For reviews, see: Synthesis, 1 (1981); Org. React., 42, 335 (1992); Org. Prep. Proced. Int., 28, 127 (1996); Synlett, 1221 (2003); Eur. J. Org. Chem., 2763 (2004):

For study of the mechanism, see: J. Org. Chem., 67, 1751 (2002).

Details for esterification of (-)-menthol with 4-nitrobenzoic acid with stereoinversion: Org. Synth. Coll., 9, 607 (1998). For an example of its use to convert a secondary alcohol to an amine by reaction with phthalimide followed by hydrazinolysis, see: Org. Synth. Coll., 7, 501 (1990). For dehydration of Boc-L-serine to the cyclic anhydride (2-oxetanone), see: Org. Synth. Coll., 9, 24 (1998).

ɑ-Amination of aldehydes can be effected in the presence of L-proline as an enantioselective catalyst, affording chiral ɑ-amino alcohols and ɑ-amino acids with good ee: Angew. Chem. Int. Ed., 41, 1790 (2002); for a similar reaction with scheme, see Dibenzyl­ azodicarboxyl­ate, L19347.

See also Di-tert-butyl­ azodicarboxyl­ate, L00294, and Diisopropyl­ azodicarboxyl­ate, L10386.

GHS Hazard and Precautionary Statements

Hazard Statements : H302-H312-H315-H319-H335-H227

Harmful if swallowed. Harmful in contact with skin. Causes skin irritation. Causes serious eye irritation. May cause respiratory irritation. Combustible liquid.

Precautionary Statements : P210-P261-P280-P305+P351+P338-P405-P501A

Keep away from heat/sparks/open flames/hot surfaces. - No smoking. 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. Store locked up. Dispose of contents/container in accordance with local/regional/national/international regulations.

Harmful or Irritant

Other References

Beilstein: 908662
UN#: UN2810
Hazard Class: 6.1
Packing Group: III
Harmonized Tariff Code: 2927.00
TSCA: No
Diethyl azodicarboxylate, 97% - CAS 1972-28-7 - Formula C6H10N2O4

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