Diethyl azodicarboxylate

• Catalog No.: L19348
• CAS Number: 1972-28-7
• M. F.: C6H10N2O4
• M. W.: 174.1546
• Purity: 97%

SYNONYMS

• Title: 偶氮二甲酸二乙酯
• IUPAC name: N-[(ethoxycarbonyl)imino]ethoxyformamide
• IUPAC Traditional name: diethyl azodicarboxylate
• Synonyms: Azodicarboxylic Acid Diethyl Ester; DEAD

DATABASE IDS

• MDL Number: MFCD00009103
• CAS Number: 1972-28-7
• Beilstein Number: 908662
• EC Number: 217-821-7

PROPERTIES

• Purity: 97%
• Boiling Point: 106°C/13mm
• Density: 1.106
• Flash Point: 85°C(185°F)
• Refractive Index: 1.4210
• GHS Hazard statements: H302-H312-H315-H319-H335-H227
• European Hazard Symbols: X
• GHS Precautionary statements: P210-P305+P351+P338-P302+P352-P321-P405-P501A
• Risk Statements: 5-21/22-36/37/38
• Safety Statements: 26-36/37-60
• Storage Warning: Air Sensitive
• TSCA Listed: 否
• Hazard Class: 6.1
• UN Number: UN2810
• Packing Group: III

REFERENCES

• 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.
• 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.
• 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 S_N2 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).
• Explosion risk by heating undiluted material.
• Secondary and tertiary amines have been dealkylated by reaction with DEAD under mild conditions, followed by acid hydrolysis: J. Org. Chem., 38, 1652 (1973).