Substance
ID:738472
Names and Identifiers
IUPAC name
N-[(ethoxycarbonyl)imino]ethoxyformamide
IUPAC Traditional name
diethyl azodicarboxylate
Synonyms
DEADDiethyl azodicarboxylate偶氮二甲酸二乙酯Azodicarboxylic Acid Diethyl Ester
Registration numbers
CAS Number
MDL Number
Beilstein Number
EC Number
Properties
Safety Information
Storage Warning
Air Sensitive
Hazard Class
6.1
European Hazard Symbols
Harmful (X)Packing Group
III
GHS Pictograms
Acute toxicity (oral, dermal, inhalation), category 4
Skin irritation, category 2
Eye irritation, category 2
Skin sensitisation, category 1
Specific Target Organ Toxicity – Single exposure, category 3
UN Number
UN2810
Safety Statements
26-36/37-60
TSCA Listed
否
GHS Hazard statements
H302-H312-H315-H319-H335-H227
GHS Precautionary statements
P210-P305+P351+P338-P302+P352-P321-P405-P501A
Risk Statements
5-21/22-36/37/38
Product Information
Purity
97%
Physical Property
Flash Point
85°C(185°F)
Boiling Point
106°C/13mm
Refractive Index
1.4210
Density
1.106
Molecule Details
No Data Available
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Molecular Spectra
No Data Available
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References
• For study of the mechanism, see: J. Org. Chem., 67, 1751 (2002).
• 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):
• 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).
• 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).
• 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.
• 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.